Jason Heyward

The son of Dartmouth graduates, Jason Heyward was born on August 9, 1989,{{Cite web |last=Sickels |first=John |date=July 24, 2009 |title=Prospect Smackdown: Jason Heyward vs. Mike Stanton |url=https://www.minorleagueball.com/2009/7/24/961747/prospect-smackdown-jason-heyward |access-date=August 5, 2019 |website=Minor League Ball}} in Ridgewood, New Jersey. His father, Eugene, is from Beaufort, South Carolina, and his mother, Laura, is from New York City; they met at Dartmouth. Eugene played basketball and majored in engineering and Laura studied French.{{Cite magazine |last=McGrath |first=Ben |date=April 12, 2010 |title=The rainy season |url=http://www.newyorker.com/magazine/2010/04/12/the-rainy-season-3 |access-date=December 26, 2014 |magazine=The New Yorker}} Eugene's uncle, Kenny Washington, played basketball for two John Wooden-led NCAA championship UCLA teams in 1964 and 1965.{{Cite web |last=Gammons |first=Peter |author-link=Peter Gammons |date=March 9, 2010 |title=Heyward works hard to play hard |url=http://mlb.mlb.com/news/print.jsp?ymd=20100309&content_id=8723826&c_id=mlb&fext=.jsp |access-date=December 27, 2014 |website=MLB.com}} Jason has one younger brother, Jacob (b. 1995), who attended the University of Miami and played baseball for the Hurricanes.{{Cite web |title=Jacob Heyward bio |url=http://www.hurricanesports.com/ViewArticle.dbml?ATCLID=209261774 |access-date=December 27, 2014 |publisher=University of Miami Hurricanes |archive-date=December 28, 2014 |archive-url=https://web.archive.org/web/20141228000051/http://www.hurricanesports.com/ViewArticle.dbml?ATCLID=209261774 |url-status=dead }} Jacob was drafted by the San Francisco Giants in 2016.{{Cite web |title=Jacob Heyward #85 |url=https://www.mlb.com/player/jacob-heyward-641689?stats=career-r-hitting-minors&year=2020 |access-date=July 24, 2020 |website=MLB.com}}

The Heywards moved to the Atlanta metropolitan area soon after he was born. Jason played and showed marked ability in baseball from an early age. Before he turned 10, he played for a national championship. Eugene helped fuel both of his sons' passion for baseball. He dedicated himself to driving them to every tournament and competition possible in the family Chevrolet Suburban, which racked up hundreds of thousands of miles between the events and his 90-minute work commute to and from Robins Air Force Base to the south in Houston County.{{Cite news |last=Goold |first=Derrick |date=March 7, 2015 |title=Heyward is at a crossroads |work=St. Louis Post-Dispatch |url=http://www.stltoday.com/sports/baseball/professional/heyward-is-at-a-crossroads/article_05560f20-5e4b-5df4-85bd-e25fb21f7c91.html |access-date=March 7, 2015}}

While his father emphasized that working hard and approaching the game with discipline were important, he also stressed that baseball was to be, above all else, fun. Heyward has maintained this same approach throughout his youth and professional career. One tournament in which he played was the renowned East Cobb Baseball program, where he was a standout and has produced other major league players. Heyward attended Henry County High School in McDonough near Atlanta. Heyward briefly played basketball in his youth but concentrated exclusively on baseball in high school at his father's urging. In February 2010, an Associated Press reporter learned from a varsity coach that Heyward's early batting practice exploits proved fatal to an oak tree in deep center field at the high school playing field.

Facing off against future Major League Baseball (MLB) catcher Buster Posey of Lee County High in the Georgia Class AAAA baseball championship during Heyward's sophomore year, Henry County won two of the best-of-three series. Posey was actually the starting pitcher in the first game as Henry Country prevailed, 2–1. Heyward hit a game-tying {{convert|400|ft|m|abbr=on}} home run in Game 2 to cap an eight-run comeback, but Lee County prevailed 14–10. The next game, Heyward's three-run single was the game and series winner in a 16–14 outcome.{{Cite news |last=Witz |first=Billy |date=October 8, 2010 |title=Schoolboys meet again, with more on the line |work=The New York Times |url=https://www.nytimes.com/2010/10/09/sports/baseball/09teammates.html?module=Search&mabReward=relbias%3As |access-date=December 29, 2014}} During his junior season, he again helped lead the Henry County High Warhawks to the state championship.{{Cite news |last=Jackson |first=Johnny |date=February 2, 2010 |title=Heyward returns to inspire students |work=Henry Daily Herald |url=http://www.henryherald.com/news/2010/feb/02/heyward-returns-to-inspire-students/ |access-date=December 27, 2014}} As a senior, he batted .520 with eight home runs (HR) and 29 runs batted in (RBIs).{{Cite web |last=Bowman |first=Mark |date=August 12, 2007 |title=Braves sign No. 1 pick Heyward |url=http://atlanta.braves.mlb.com/news/article.jsp?ymd=20070812&content_id=2145265&vkey=news_atl&fext=.jsp&c_id=atl |archive-url=https://web.archive.org/web/20110616122711/http://atlanta.braves.mlb.com/news/article.jsp?ymd=20070812&content_id=2145265&vkey=news_atl&fext=.jsp&c_id=atl |url-status=dead |archive-date=June 16, 2011 |website=MLB.com}}

One of Heyward's close friends and teammates from the 2005 AAAA Georgia state championship team, Andrew Wilmot, died in a traffic collision while attending college.{{Cite web |last=Berler |first=Ron |date=2010 |title=Honoring number 22: The inspiring story behind Braves right-fielder Jason Heyward's jersey |url=http://www.guideposts.org/inspirational-stories/inspiring-story-jason-heyward-wears-number-22-honor-best-friend |access-date=December 29, 2014 |website=Guideposts |archive-date=December 30, 2014 |archive-url=https://web.archive.org/web/20141230053700/http://www.guideposts.org/inspirational-stories/inspiring-story-jason-heyward-wears-number-22-honor-best-friend |url-status=dead }} Wilmot was a catcher who wore the uniform number 22, the number Heyward would later wear in his major league career to honor him. Wilmot's mother, Tammie Ruston, was Heyward's high school literature teacher in his senior year.{{Cite web |last=Langosh |first=Jenifer |date=November 25, 2014 |title=Matheny offers to give No. 22 to Heyward |url=http://m.cardinals.mlb.com/news/article/102419696/cardinals-manager-mike-matheny-offers-to-give-jersey-no-22-to-jason-heyward |archive-url=https://web.archive.org/web/20141127210840/http://m.cardinals.mlb.com/news/article/102419696/cardinals-manager-mike-matheny-offers-to-give-jersey-no-22-to-jason-heyward |url-status=dead |archive-date=November 27, 2014 |access-date=December 15, 2014 |website=MLB.com}}

Numerous colleges showed interest and recruited Heyward, including UCLA, which offered a full-ride scholarship due in part to the family connection. Heyward was also especially interested in Clemson and Georgia Tech.{{Cite news |title=Chat with Jason Heyward |work=SportsNation |publisher=ESPN |url=http://espn.go.com/sportsnation/chat/_/id/30564/braves-jason-heyward |archive-url=https://web.archive.org/web/20100131113152/http://espn.go.com/sportsnation/chat/_/id/30564/braves-jason-heyward |url-status=dead |archive-date=January 31, 2010 |access-date=November 3, 2015}} Concurrently, the hometown Atlanta Braves had followed and scouted him for years, while attempting to conceal their excitement.

Heyward was the 14th overall selection by Atlanta in the 2007 Major League Baseball draft. Despite signing a National Letter of Intent with UCLA, he chose professional baseball over college and signed a contract with the team worth $1.7 million.{{Cite web |date=August 15, 2007 |title=Two UCLA Baseball Recruits Sign Major League Deals |url=http://uclabruins.cstv.com/sports/m-basebl/spec-rel/081507aaa.html |url-status=dead |archive-url=https://web.archive.org/web/20080207054836/http://uclabruins.cstv.com/sports/m-basebl/spec-rel/081507aaa.html |archive-date=February 7, 2008 |publisher=UCLA Baseball}}

At age 17, Heyward began his professional career in Minor League Baseball in the Braves' system. He played for both the Gulf Coast League Braves and the Danville Braves of the Appalachian League in 2007. He homered in his first professional game.{{Cite web |title=Jason Heyward stats, video and highlights: Bio, 2007 season |url=http://stlouis.cardinals.mlb.com/team/player.jsp?player_id=518792#gameType=%27R%27§ionType=career&statType=1&season=2014&level=%27ALL%27 |archive-url=https://web.archive.org/web/20141119165136/http://stlouis.cardinals.mlb.com/team/player.jsp?player_id=518792#gameType=%27R%27§ionType=career&statType=1&season=2014&level=%27ALL%27 |url-status=dead |archive-date=November 19, 2014 |access-date=January 11, 2015 |website=St. Louis Cardinals |publisher=MLB.com}} In 12 minor league contests in 2007, he batted .302 with one home run and six RBIs. In 2007, Baseball America selected Heyward as the Braves' top overall prospect and the organization's best power hitter; it cited Heyward as having the best strike zone discipline and excelling at multiple other skills.{{Cite web |date=November 5, 2007 |title=Top 10 Prospects: Atlanta Braves |url=http://www.baseballamerica.com/today/prospects/features/265139.html |website=Baseball America}}

Heyward split the 2008 season between Class-A Rome of the South Atlantic League (SAL) and Advanced-A Myrtle Beach of the Carolina League.{{Cite web |title=Jason Heyward minor league statistics & history |url=https://www.baseball-reference.com/minors/player.cgi?id=heywar001jas |access-date=June 16, 2015 |website=Baseball-Reference.com}} He was named the club's Player of the Month in April.{{Cite web |title=Jason Heyward stats, video, and highlights: Bio, 2008 season |url=http://stlouis.cardinals.mlb.com/team/player.jsp?player_id=518792#gameType=%27R%27§ionType=career&statType=1&season=2014&level=%27ALL%27 |archive-url=https://web.archive.org/web/20141119165136/http://stlouis.cardinals.mlb.com/team/player.jsp?player_id=518792#gameType=%27R%27§ionType=career&statType=1&season=2014&level=%27ALL%27 |url-status=dead |archive-date=November 19, 2014 |access-date=January 11, 2015 |website=St. Louis Cardinals |publisher=MLB.com}} While playing for Rome, Heyward had 42 multi-hit games, including two four-hit games. He finished in the top three in nine offensive categories for the club.

The Braves promoted Heyward to Myrtle Beach on August 25, 2008. He played seven games there. Following the 2008 season, Baseball America named Heyward the South Atlantic League's Most Outstanding Prospect, Top Batting Prospect, and Most Exciting Player. He was also a Baseball America All-Star for the entire minor leagues, Mid- and Post-Season All-Star, Low-Class A All-Star, and the Braves' second-best prospect. MLB.com named him the third-best overall minor league prospect. ESPN.com named him the minor leagues' best corner outfield prospect, the #1 Atlanta prospect, and third-overall minor-league prospect.

Heyward started the 2009 season at Myrtle Beach and then gained successive promotions to Double-A Mississippi and Triple-A Gwinnett. He was named the Carolina League Player of the Week on May 18. Heyward was selected to the Carolina League All-Star team but missed the game due to an oblique injury. He participated in the All-Star Futures Game at Busch Stadium.{{Cite web |title=Jason Heyward stats, video, and highlights: Bio, 2009 season |url=http://stlouis.cardinals.mlb.com/team/player.jsp?player_id=518792#gameType=%27R%27§ionType=career&statType=1&season=2014&level=%27ALL%27 |archive-url=https://web.archive.org/web/20141119165136/http://stlouis.cardinals.mlb.com/team/player.jsp?player_id=518792#gameType=%27R%27§ionType=career&statType=1&season=2014&level=%27ALL%27 |url-status=dead |archive-date=November 19, 2014 |access-date=January 11, 2015 |website=St. Louis Cardinals |publisher=MLB.com}} On July 4, the Braves promoted Heyward to Mississippi, where he was named the team's Player of the Month. From September 5–7, he appeared with the Gwinnett Braves of the Triple-A of the International League. He also played four games with the Peoria Saguaros of the Arizona Fall League (AFL). That September, both Baseball America and USA Today named Heyward their Minor League Player of the Year.{{Cite web |date=September 11, 2009 |title=Jason Heyward honored by USA Today & Baseball America |url=http://www.oursportscentral.com/services/releases/?id=3904295 |access-date=September 28, 2010 |publisher=OurSports Central}} He won the Braves' Hank Aaron Award (not to be confused with MLB's Hank Aaron Award), conferred annually to the top offensive player in the Braves organization.

Entering the 2010 season, Baseball America, Keith Law of ESPN.com and Jonathan Mayo of MLB.com each listed Heyward as baseball's top prospect;{{Cite web |last=Law |first=Keith |author-link=Keith Law (baseball writer) |date=January 28, 2010 |title=Ranking the top prospects |url=https://insider.espn.com/mlb/insider/columns/story?columnist=law_keith&id=4856310 |website=ESPN.com}} BA ranked him ahead of Stephen Strasburg and Giancarlo Stanton.{{Cite web |last=Staff reports |date=February 23, 2010 |title=Top 100 Prospects: No. 1−20 |url=http://www.baseballamerica.com/today/prospects/rankings/top-100-prospects/2010/269546.html |access-date=December 25, 2014 |website=Baseball America}} The Braves added Heyward to their 40-man roster before the 2010 season began.

File:DSC00828 Jason Heyward.jpg in 2010{{Cite web |title=Jason Heyward 2010 batting game logs |url=https://www.baseball-reference.com/players/gl.cgi?id=heywaja01&t=b&year=2010 |access-date=May 31, 2015 |website=Baseball-Reference.com}}]]

After Heyward made a rapid ascent through the minor leagues, the Braves invited him to spring training in March 2010. There, his hitting continued to draw notice; he routinely hit "rockets" all over the field and over the fences, compelling manager Bobby Cox to make him a regular in the lineup. Cox mentioned that the balls Heyward hit made a different, more pronounced sound than the balls hit by other players.{{Cite news |last=Thompson |first=Phil |date=December 11, 2015 |title=5 things to know about Jason Heyward |work=Chicago Tribune |url=https://www.chicagotribune.com/sports/cubs/ct-5-things-jason-heyward-cubs-spt-1212-20151211-story.html |access-date=July 24, 2020}} Heyward hit two notable batting practice home runs at the Champion Stadium training complex in Lake Buena Vista, Florida. One damaged a Coca-Cola truck in the parking lot, and another broke the sunroof of Atlanta Braves' assistant general manager Bruce Manno's car. He was initially issued uniform number 71. At the end of spring training, he asked for and received number 22, which he wore in memory of his deceased high school teammate, Andrew Wilmot.

Heyward was one of the most anticipated prospects in all of baseball. Shirts depicting his nickname, "The J-Hey Kid," were in high demand before he even played his first official major league game. Fans and pundits prognosticated on a future Hall of Fame career, comparing Heyward to former greats such as Darryl Strawberry, Willie McCovey and Willie Mays, among many others. In fact, the "J-Hey Kid" nickname was drawn from Mays' nickname, "The Say Hey Kid." On March 26, after Heyward led the club in on-base percentage and slugging percentage in spring training, the Braves named him their starting right fielder.

During his first MLB plate appearance – and on his first swing at an MLB pitch – Heyward hit a three-run home run, estimated at {{convert|471|ft|m}}, off of starter Carlos Zambrano.{{Cite web |date=April 5, 2010 |title=Heyward goes yard in first AB |url=https://www.mlb.com/video/heyward-goes-yard-in-first-ab-c7282459 |access-date=July 24, 2020 |website=MLB.com}} Heyward became the fifth player in Braves history to hit a home run in his first major league at-bat and the 11th in franchise history to do so in his MLB debut.{{Cite web |last=Bowman |first=Mark |date=April 5, 2010 |title=Heyward adds to legend in first at-bat |url=http://mlb.mlb.com/news/article.jsp?ymd=20100405&content_id=9088530&vkey=affililiate&fext=.jsp&c_id=atl |publisher=braves.mlb.com}}

Through Atlanta's first 50 games, Heyward lived up to the hype that surrounded him, hitting 10 home runs while batting .301 with a .421 OBP and .596 slugging percentage.{{Cite magazine |last=Corcoran |first=Cliff |date=November 17, 2014 |title=Cardinals, Braves betting on potential with Heyward-Miller trade |url=https://www.si.com/mlb/2014/11/17/jason-heyward-shelby-miller-trade-cardinals-braves-mlb |access-date=February 13, 2015 |magazine=Sports Illustrated}} He was named the National League (NL) Rookie of the Month in both April{{Cite web |last=Gonzalez |first=Alden |date=May 4, 2010 |title=Heyward, Jackson named April's top rookies |url=http://mlb.mlb.com/news/article.jsp?ymd=20100504&content_id=9785294&vkey=news_mlb&fext=.jsp&c_id=mlb |url-status=dead |archive-url=https://web.archive.org/web/20100507081502/http://mlb.mlb.com/news/article.jsp?ymd=20100504&content_id=9785294&vkey=news_mlb&fext=.jsp&c_id=mlb |archive-date=May 7, 2010 |access-date=September 28, 2010 |website=MLB.com}} and May.{{Cite web |last=Stephens |first=Bailey |date=June 2, 2010 |title=Heyward, Boesch named top May rookies |url=http://atlanta.braves.mlb.com/news/article.jsp?ymd=20100602&content_id=10721656&vkey=news_atl&fext=.jsp&c_id=atl |url-status=dead |archive-url=https://web.archive.org/web/20100605055733/http://atlanta.braves.mlb.com/news/article.jsp?ymd=20100602&content_id=10721656&vkey=news_atl&fext=.jsp&c_id=atl |archive-date=June 5, 2010 |access-date=September 28, 2010 |publisher=Atlanta.braves.mlb.com}} However, after sustaining a thumb injury while sliding in May, Heyward missed playing time. After he returned later in the season, his performance declined and consistency was elusive. He was selected as a starter for the NL All-Star team, but did not participate due to his thumb injury.{{Cite web |last=Jackson |first=Tony |date=July 12, 2010 |title=Dodgers' Kuo added to All-Star Game |url=https://www.espn.com/los-angeles/mlb/news/story?id=5371297 |access-date=December 15, 2014 |publisher=ESPN}}

Heyward stole home in a double steal against the Washington Nationals in the first inning on July 28. In so doing, he became the first Brave to steal home since Rafael Furcal, who had done so more than ten years earlier.{{Cite web |date=July 28, 2010 |title=Heyward swipes home on double steal |url=http://m.braves.mlb.com/news/article/12740636/ |url-status=dead |archive-url=https://web.archive.org/web/20150712150609/http://m.braves.mlb.com/news/article/12740636/ |archive-date=July 12, 2015 |access-date=December 15, 2014 |website=MLB.com}} A 16–5 victory over the Cubs on August 22 featured Heyward's first MLB multi-home run game, as well as career highs in hits and runs scored with four each.{{Cite web |last=Bowman |first=Mark |date=August 22, 2010 |title=Infante, Heyward provide muscle for Braves |url=http://m.braves.mlb.com/news/article/13778026/ |url-status=dead |archive-url=https://web.archive.org/web/20160304054038/http://m.braves.mlb.com/news/article/13778026/ |archive-date=March 4, 2016 |access-date=January 11, 2015 |website=MLB.com}} In the final 112 games of the season, Heyward batted .266 with a .381 OBP and .396 SLG.

Heyward made his postseason debut on October 7, 2010, in the National League Division Series (NLDS) against the San Francisco Giants.{{Cite web |last=Langosch |first=Jenifer |date=October 7, 2010 |title=After playoff debut, Heyward looks forward |url=http://m.braves.mlb.com/news/article/15492592/ |url-status=dead |archive-url=https://web.archive.org/web/20150123170550/http://m.braves.mlb.com/news/article/15492592/ |archive-date=January 23, 2015 |access-date=January 11, 2015 |website=MLB.com}} San Francisco eliminated Atlanta, and Heyward had just two hits in the entire series.{{Cite news |date=October 11, 2010 |title=Giants advance to NLCS by sending off Braves and manager Bobby Cox |url=http://scores.espn.go.com/mlb/recap?gameId=301011115 |url-status=dead |archive-url=https://web.archive.org/web/20101014190618/http://scores.espn.go.com/mlb/recap?gameId=301011115 |archive-date=October 14, 2010 |access-date=January 11, 2015 |work=ESPN|agency=Associated Press}}

Heyward finished his first major league season with a .277 batting average, a .393 on-base percentage, 18 home runs, and 83 runs scored in 142 regular season games. He ranked fourth overall in the NL in OBP and walks.{{Cite web |title=Jason Heyward statistics and history |url=https://www.baseball-reference.com/players/h/heywaja01.shtml |access-date=November 23, 2023 |website=Baseball-Reference.com}} Heyward was named the Sporting News NL Rookie of the Year,{{Cite web |date=October 19, 2010 |title=Heyward, Jackson named Sporting News' rookies of the year |url=http://www.sportingnews.com/mlb/feed/2010-10/2010-baseball-awards/story/heyward-jackson-named-sporting-news-rookies-of-the-year |access-date=December 24, 2014 |website=Sporting News |archive-date=December 28, 2014 |archive-url=https://web.archive.org/web/20141228061403/http://www.sportingnews.com/mlb/feed/2010-10/2010-baseball-awards/story/heyward-jackson-named-sporting-news-rookies-of-the-year |url-status=dead }} the Baseball America MLB Rookie of the Year; he was also named to the Baseball America All-Rookie Team{{Cite web |last=Eddy |first=Matt |date=October 19, 2010 |title=Future big league stars highlight all-rookie team |url=http://www.baseballamerica.com/today/majors/awards/rookie-of-the-year/2010/2610794.html |access-date=October 21, 2010 |website=Baseball America}} and to Topps' Major League Rookie All-Star Team.{{Cite web |last=Thesier |first=Kelly |date=November 29, 2010 |title=Valencia awarded with rookie honor |url=http://minnesota.twins.mlb.com/news/article.jsp?ymd=20101129&content_id=16225164&vkey=news_min&c_id=min |access-date=December 11, 2010 |website=MLB.com |archive-date=December 8, 2010 |archive-url=https://web.archive.org/web/20101208192811/http://minnesota.twins.mlb.com/news/article.jsp?ymd=20101129&content_id=16225164&vkey=news_min&c_id=min |url-status=dead }} He finished second in the voting for the NL Rookie of the Year award.{{Cite web |last=Haft |first=Chris |date=November 15, 2010 |title=Posey catches NL Rookie of the Year honors |url=http://m.mlb.com/news/article/16099576/ |url-status=dead |archive-url=https://web.archive.org/web/20150712162116/http://m.mlb.com/news/article/16099576/ |archive-date=July 12, 2015 |access-date=December 15, 2010 |website=MLB.com}}

Heyward's second MLB season commenced in a fashion that reprised the high expectations from his rookie season, but injuries ultimately led to a lengthy and dramatic slump. In the spring, Heyward was diagnosed with a degenerative condition in his lower back. He hit a home run off of Nationals pitcher Liván Hernández in his first at-bat of the season on March 31. He became just the second MLB player, after Kazuo Matsui, to homer in his first major league at-bat on Opening Day and to hit a home run in his first at-bat of the following season.{{Cite web |date=March 31, 2011 |title=Heyward hits another Opening Day homer |url=http://m.braves.mlb.com/news/article/17225532/ |url-status=dead |archive-url=https://web.archive.org/web/20150712145154/http://m.braves.mlb.com/news/article/17225532/ |archive-date=July 12, 2015 |access-date=July 11, 2015 |publisher=atlanta.braves.mlb.com}} In a back-and-forth game with the Giants on April 24, he hit a go-ahead home run off relief pitcher Jeremy Affeldt in a 9–6, ten-inning victory.{{Cite web |last=Kriochik |first=Ron |date=April 24, 2011 |title=San Francisco bullpen falters in 10-inning loss |url=http://www.sfgate.com/sports/article/SF-Giants-bullpen-stumbles-in-10-inning-loss-2374230.php |access-date=January 10, 2015 |website=San Francisco Chronicle}}

Having previously been represented by Victor Menocal from Career Sports Entertainment (CSE) until Menocal resigned from CSE, news emerged on May 6 that Heyward had made Casey Close his new agent.{{Cite web |last=Bowman |first=Mark |date=May 6, 2011 |title=Braves outfielder Heyward changes agents |url=http://m.mlb.com/news/article/18709988/ |url-status=dead |archive-url=https://web.archive.org/web/20141120000830/http://m.mlb.com/news/article/18709988 |archive-date=November 20, 2014 |access-date=January 10, 2015 |website=MLB.com}}

From the beginning of spring training, Heyward endured lingering shoulder soreness. After Heyward collected just four hits in his first 41 at-bats in May,{{Cite web |last=Sullivan |first=Jeff |date=May 22, 2014 |title=Jason Heyward shoulder injury sends Braves slugger to DL |url=https://www.sbnation.com/2011/5/22/2184961/jason-heyward-injury-braves-shoulder |access-date=December 30, 2014 |publisher=SB Nation}} the Braves performed a magnetic resonance imaging (MRI) scan on May 12 which revealed an inflamed rotator cuff, but no structural damage.{{Cite web |date=May 12, 2011 |title=Braves' Jason Heyward out again |url=https://www.espn.com/mlb/news/story?id=6535384 |access-date=June 4, 2015 |publisher=ESPN |agency=Associated Press}} He rested and received a cortisone injection, but aggravated the injury days later during batting practice. The Braves placed him on the disabled list (DL) on May 22. The following month, teammate Chipper Jones publicly criticized Heyward for not playing through his injuries; Jones said, "I think where Jason might have erred was the comment that he made, 'I'm not coming back until it doesn't hurt anymore.' ... What Jason needs to realize is that Jason at 80 percent is a force, and Jason at 80 percent is better than a lot of people in this league".{{Cite web |date=June 8, 2011 |title=Chipper Jones calls out Jason Heyward |url=https://www.espn.com/mlb/news/story?id=6640173&src=mobile |access-date=January 17, 2015 |publisher=ESPN |agency=Associated Press}} Jones later explained that he reassured Heyward in a phone call that he did not intend to misrepresent Heyward's efforts to rehabilitate.{{Cite news |last=Rogers |first=Carroll |date=June 14, 2011 |title=Jones clarifies comments in phone call to Heyward |work=The Atlanta Journal-Constitution |url=http://www.ajc.com/news/sports/baseball/jones-clarifies-comments-in-phone-call-to-heyward/nQwQX/ |access-date=January 17, 2015}}

Upon his return from the DL, Heyward experienced difficulty driving the ball.{{Cite web |last=Vooris |first=Ryan |date=August 8, 2011 |title=Jason Heyward and why he has struggled for the Atlanta Braves in 2011 |url=http://bleacherreport.com/articles/793218-jason-heyward-and-why-hes-struggled-for-the-atlanta-braves-in-2011 |access-date=December 30, 2014 |publisher=Bleacher Report}} A sixth-inning home run against the Baltimore Orioles on July 1 was Heyward's first since April 29 against the St. Louis Cardinals, a span of 104 at-bats.{{Cite news |title=Jason Heyward stats, video, and highlights: Bio, 2011 season |work=St. Louis Cardinals |publisher=MLB |url=http://stlouis.cardinals.mlb.com/team/player.jsp?player_id=518792#gameType=%27R%27§ionType=career&statType=1&season=2014&level=%27ALL%27 |archive-url=https://web.archive.org/web/20141119165136/http://stlouis.cardinals.mlb.com/team/player.jsp?player_id=518792#gameType=%27R%27§ionType=career&statType=1&season=2014&level=%27ALL%27 |url-status=dead |archive-date=November 19, 2014 |access-date=January 10, 2015}} During a game against the Chicago Cubs on August 23, Heyward hit his first career grand slam.{{Cite news |last=O'Brien |first=David |date=August 24, 2011 |title=Heyward slam fuels Braves' win against Cubs |work=The Atlanta Journal-Constitution |url=http://www.ajc.com/sports/atlanta-braves/heywards-slam-fuels-braves-1135775.html |access-date=August 22, 2012}}

Through the end of August, the Braves were the NL wild card leader. However, the Cardinals overcame a {{frac|10|1|2}}-game deficit for the wild card position by winning 20 of their final 28 games, eliminating the Braves from the playoffs on the final day of the season. The Braves' failure to make the playoffs was one of the epic late-season collapses in MLB history.{{Cite news |last=Tierney |first=Mike |date=September 29, 2011 |title=Braves complete collapse in 13-inning loss to Phillies |work=The New York Times |url=https://www.nytimes.com/2011/09/29/sports/baseball/braves-complete-collapse-in-13-inning-loss-to-phillies.html?_r=0 |access-date=April 5, 2014}}{{Cite news |last=Hummel |first=Rick |author-link=Rick Hummel |date=November 20, 2013 |title=9 Chris Carpenter games we'll never forget |work=St. Louis Post-Dispatch |url=http://www.stltoday.com/gallery/sports/baseball/professional/chris-carpenter-games-we-ll-never-forget/collection_f68337ea-0ff9-57e8-b8cb-49d763c8aa75.html#3 |access-date=December 9, 2013}} Heyward's overall performance dropped off from his performance during his rookie season. His batting average dropped 50 points to .227; his other contributions, also in decline, included 14 home runs and 42 RBIs in 128 games.

File:Jason Heyward.jpg before a spring training game in 2011]]

In an effort to improve his performance, Heyward took extra steps in his preseason preparation. He streamlined his swing to mitigate bad habits incorporated after the shoulder injury. He modified his diet to include more fruits, chicken, and fish. Further, he participated in physical therapy to strengthen the shoulder and worked for a leaner weight, dropping from {{convert|256|lb}} to {{convert|235|lb}}.{{Cite news |last=Rogers |first=Carroll |date=January 31, 2012 |title=Jason Heyward optimistic about re-tooled swing |work=The Atlanta Journal-Constitution |url=http://www.ajc.com/news/sports/baseball/jason-heyward-optimistic-about-re-tooled-swing/nQQtw/ |access-date=January 16, 2015}} He started the 2012 season slowly. However, his bases-loaded double on May 13 off Lance Lynn drove in the game-winning run as the Braves triumphed over the Cardinals, 7–4.{{Cite news |last=Rogers |first=Carroll |date=May 13, 2012 |title=Braves complete sweep of Cardinals |work=The Atlanta Journal-Constitution |url=http://www.ajc.com/news/sports/baseball/braves-complete-sweep-of-cardinals/nQTnJ/ |access-date=January 25, 2015}}

On June 7, Heyward's first multi-HR game of the season (and the second of his career) helped secure an 8–2 victory over the Marlins.{{Cite news |last=O'Brien |first=David |date=June 8, 2012 |title=Heyward homers twice; Braves complete sweep in Miami |work=The Atlanta Journal-Constitution |url=http://www.ajc.com/news/sports/baseball/heyward-homers-twice-braves-complete-sweep-in-miam/nQWNY/ |access-date=January 25, 2015}} On June 19, he threw the New York Yankees' Mark Teixeira out at home plate, preserving a 4–3 win.{{Cite web |date=June 30, 2012 |title=Heyward impressing with arm strength, accuracy |url=http://m.braves.mlb.com/news/article/34216962/ |url-status=dead |archive-url=https://web.archive.org/web/20141228061529/http://m.braves.mlb.com/news/article/34216962/ |archive-date=December 28, 2014 |access-date=December 27, 2014 |publisher=braves.mlb.com}} In a 12-game hitting streak that spanned from June 13 to 27, Heyward batted .455 (20-for-44) and homered four times.{{Cite web |title=Jason Heyward stats, video, and highlights: Bio, 2012 season |url=http://stlouis.cardinals.mlb.com/team/player.jsp?player_id=518792#gameType=%27R%27§ionType=career&statType=1&season=2014&level=%27ALL%27 |archive-url=https://web.archive.org/web/20141119165136/http://stlouis.cardinals.mlb.com/team/player.jsp?player_id=518792#gameType=%27R%27§ionType=career&statType=1&season=2014&level=%27ALL%27 |url-status=dead |archive-date=November 19, 2014 |access-date=January 16, 2015 |website=St. Louis Cardinals |publisher=MLB.com}}

After the season, Heyward captured his first career defensive awards: an MLB Fielding Bible Award and a National League Rawlings Gold Glove Award.{{Cite web |title=The 2012 awards |url=http://www.fieldingbible.com/the-2012-winners.asp |access-date=December 26, 2014 |website=Fielding Bible}}{{Cite web |date=October 25, 2012 |title=The 2012 Awards |url=http://www.actasports.com/stats_detail/?StatId=345 |url-status=dead |archive-url=https://web.archive.org/web/20121027035418/http://www.actasports.com/stats_detail/?StatId=345 |archive-date=October 27, 2012 |publisher=ACTA Sports}} In 158 games, he batted .269 with career highs of 27 home runs, 82 RBIs, and 21 stolen bases.

On January 18, 2013, the Braves avoided salary arbitration with Heyward by signing him to a one-year, $3.65 million deal. The Braves' outfield also included newly acquired brothers Justin and B. J. Upton,{{Cite web |last=Bowman |first=Mark |date=January 18, 2013 |title=Heyward, four other Braves avoid arbitration |url=http://mlb.mlb.com/news/article.jsp?ymd=20130118&content_id=41019756&vkey=news_mlb&c_id=mlb |website=MLB.com}} with whom Heyward would play for the remainder of his Braves tenure. An appendectomy on April 22 led to Heyward being placed on the 15-day disabled list.{{Cite web |title=Jason Heyward stats, video, and highlights: Bio, 2013 season |url=http://stlouis.cardinals.mlb.com/team/player.jsp?player_id=518792#gameType=%27R%27§ionType=career&statType=1&season=2014&level=%27ALL%27 |archive-url=https://web.archive.org/web/20141119165136/http://stlouis.cardinals.mlb.com/team/player.jsp?player_id=518792#gameType=%27R%27§ionType=career&statType=1&season=2014&level=%27ALL%27 |url-status=dead |archive-date=November 19, 2014 |access-date=December 21, 2014 |website=St. Louis Cardinals |publisher=MLB.com}} He returned from the appendectomy on May 17, going 2-for-4 in an 8–5 win against the Dodgers.

New York Mets pitcher Jon Niese hit Heyward in the face with a pitch on August 21, fracturing his jaw in two places.{{Cite news |last=Rogers |first=Carroll |date=August 21, 2013 |title=Jason Heyward has surgery on jaw |work=The Atlanta Journal-Constitution |url=http://www.ajc.com/news/sports/baseball/jason-heyward-injury-dampens-braves-victory/nZYdT/ |access-date=August 26, 2013}} He had surgery, which required the insertion of two plates, and returned on September 20. Heyward began wearing a protective shield attached to the right side of his batting helmet.{{Cite web |last=Short |first=D.J. |date=February 15, 2014 |title=Jason Heyward will continue to wear protective guard on his helmet |url=http://hardballtalk.nbcsports.com/2014/02/15/jason-heyward-will-continue-to-wear-protective-guard-on-his-helmet/ |access-date=December 24, 2014 |publisher=NBCSports}} He struck out and walked in a 9–5 win against the Chicago Cubs.{{Cite web |last=Bowman |first=Mark |date=September 21, 2013 |title=Heyward has 'blast' in return from disabled list |url=http://m.braves.mlb.com/news/article/61183798/ |url-status=dead |archive-url=https://web.archive.org/web/20141129122124/http://m.braves.mlb.com/news/article/61183798/ |archive-date=November 29, 2014 |access-date=February 23, 2015 |publisher=braves.mlb.com}} Six days later, Heyward set career highs against Philadelphia with five hits and four extra-base hits. After two stints on the DL, Heyward appeared in 104 total games, batting .254 with 14 home runs, 38 RBI, and 67 runs scored. The Braves' record was 71–33 in the games in which he appeared.

File:Heywardb2014.jpg

The Braves bought out Heyward's last arbitration-eligible years on February 4, 2014, agreeing on a two-year, $13.3 million contract.{{Cite news |date=February 4, 2014 |title=Jason Heyward, Braves reach deal |work=ESPN |url=https://www.espn.com/mlb/story/_/id/10401941/jason-heyward-atlanta-braves-agree-two-year-contract |access-date=February 4, 2014}} Already rated one of the top defensive outfielders in the league, Heyward significantly improved his coverage in right field during the early part of the season.{{Cite web |last=Petriello |first=Mike |date=May 19, 2014 |title=Jason Heyward still providing value |url=http://www.fangraphs.com/blogs/jason-heyward-and-still-providing-value/ |access-date=December 24, 2014 |publisher=Fangraphs}} Two catches on balls hit by star Mike Trout – one on a sinking line drive and one on a ball Heyward leaped to catch at the warning track – helped ensure a 7–3 victory over the Los Angeles Angels of Anaheim on June 15.{{Cite news |date=June 15, 2014 |title=Angels taken down by Atlanta Braves, 7–3 |work=The Los Angeles Times |agency=Associated Press |url=http://www.latimes.com/sports/angels/la-sp-angels-braves-box-20140616-story.html |access-date=December 28, 2014}}

Playing as the Braves' primary leadoff hitter, Heyward played in 149 games and finished with a .271 batting average, 74 runs scored, 11 home runs, 58 RBI and 20 stolen bases.{{Cite news |date=November 17, 2014 |title=Braves trade Jason Heyward, Jordan Walden for Cardinals' Shelby Miller |work=The Albany Herald |url=http://www.albanyherald.com/news/2014/nov/17/braves-trade-jason-heyward-jordan-walden-for/ |access-date=December 15, 2014}} Heyward was the recipient of several awards, including his second of both the Rawlings NL Gold Glove Award and the Fielding Bible Award for all MLB right fielders; he won the latter award unanimously.{{Cite web |title=The 2014 awards |url=http://www.fieldingbible.com/the-winners.asp |access-date=December 26, 2014 |website=Fielding Bible}} Wilson Sporting Goods named him their MLB right field Defensive Player of the Year and their overall MLB Defensive Player of the Year.{{Cite news |last=O'Brien |first=David |date=November 5, 2014 |title=Heyward chosen best defensive player by Wilson |work=The Atlanta Journal-Constitution |url=http://www.ajc.com/news/sports/baseball/heyward-chosen-best-defensive-player-by-wilson/nh2KL/ |access-date=December 15, 2014}}

On November 17, 2014, the Braves traded Heyward to the St. Louis Cardinals along with pitcher Jordan Walden for pitchers Shelby Miller and Tyrell Jenkins to replace their former right fielder and top prospect Oscar Taveras, who died in a car accident a month earlier.{{Cite web |last=Bowman |first=Mark |date=November 17, 2014 |title=Cards get Heyward from Braves in four-player swap |url=https://www.mlb.com/news/braves-acquire-pitchers-shelby-miller-tyrell-jenkins-from-cardinals-for-outfield |website=MLB.com}} Cardinals manager Mike Matheny, who wore uniform #22 and had also done so for most of his playing career, gave his number to Heyward; Heyward wears this number to honor his late friend and teammate Andrew Wilmot.

File:Jason Heyward on May 18, 2015.jpg]]

On April 5, 2015, five years to the day after his MLB debut, Heyward appeared in his first game as a Cardinal. He garnered three hits, including two doubles and a stolen base in a 3–0 victory over the Chicago Cubs.{{Cite web |last=Langosch |first=Jenifer |date=April 5, 2015 |title=Hasten Jason! Heyward thrills in 3-hit Cards debut |url=http://m.mlb.com/news/article/116512248/jason-heyward-thrills-in-3-hit-cardinals-debut |archive-url=https://web.archive.org/web/20150408145907/http://m.mlb.com/news/article/116512248/jason-heyward-thrills-in-3-hit-cardinals-debut |archive-date=April 8, 2015 |access-date=April 7, 2015 |website=MLB.com}} Heyward homered in three straight games from June 22 to 24.{{Cite web |last1=Frisaro |first1=Joe |last2=Wilaj |first2=Steve |date=June 24, 2015 |title=Wong, Heyward punish Latos to lift Cards |url=https://www.mlb.com/news/kolten-wong-jason-heyward-homer-to-lift-cards/c-132708742 |access-date=June 24, 2015 |website=MLB.com}}{{Cite news |date=June 24, 2015 |title=Jason Heyward homers in third straight game, leads Cardinals past Marlins |work=USA Today |url=https://www.usatoday.com/story/sports/mlb/2015/06/24/cardinals-marlins-jason-heyward-giancarlo-stanton/29253647/ |access-date=June 25, 2015}} On July 18 against the Mets, he matched a career high with five hits in a 12–2 win.{{Cite web |last=Cobb |first=David |date=July 19, 2015 |title=Heyward matches career high with 5 hits |url=http://m.cardinals.mlb.com/news/article/137328554/jason-heyward-matches-career-high-with-5-hits?game_pk=415013 |url-status=dead |archive-url=https://web.archive.org/web/20160304093950/http://m.cardinals.mlb.com/news/article/137328554/jason-heyward-matches-career-high-with-5-hits?game_pk=415013 |archive-date=March 4, 2016 |access-date=July 19, 2015 |website=MLB.com}}

In an August 16 contest against the Marlins, Heyward hit two home runs for his first multi-home run game with the Cardinals.{{Cite news |last=Goold |first=Derrick |date=August 16, 2015 |title=Cards too generous in loss to Marlins |work=St. Louis Post-Dispatch |url=http://www.stltoday.com/sports/baseball/professional/cards-too-generous-in-loss-to-marlins/article_56718096-f882-5338-93a8-e4dd4f3aa3eb.html |access-date=August 17, 2015}} In the second game of a doubleheader against Pittsburgh on September 30, Heyward hit his second career grand slam in an 11–1 win, giving the Cardinals their 100th victory of the season while clinching their third consecutive National League Central division title. He also robbed both Francisco Cervelli and Michael Morse of hits in that game.{{Cite web |last1=Singer |first1=Tom |last2=Langosch |first2=Jenifer |date=September 30, 2015 |title=Cards rout Bucs in Game 2 to clinch Central |url=https://www.mlb.com/news/cards-rout-bucs-in-game-2-to-clinch-central-c152489984 |access-date=September 30, 2015 |website=MLB.com}}{{Cite news |last=Goold |first=Derrick |date=September 30, 2015 |title=Cards clinch third consecutive division title, win 100th game |work=St. Louis Post-Dispatch |url=http://www.stltoday.com/sports/baseball/professional/cardinal-beat/cards-clinch-third-consecutive-division-title-win-th-game/article_8bf3b8f1-46a0-52c2-9468-ecbac72d0b93.html |access-date=September 30, 2015}}

Heyward finished the season with a career-high .293 batting average, a .359 on-base percentage, and a .439 slugging percentage.{{Cite news |last=Schoenfield |first=David |date=November 24, 2015 |title=Where will Jason Heyward end up signing? |work=ESPN |url=https://www.espn.com/blog/sweetspot/post/_/id/66634/where-will-jason-heyward-end-up-signing |access-date=November 29, 2015}} Among all outfielders since 2010, Heyward's 96.2 accumulated ultimate zone rating (UZR) led the major leagues.{{Cite web |last=Todd |first=Jeff |date=October 30, 2015 |title=Free agent profile: Jason Heyward |url=http://www.mlbtraderumors.com/2015/10/free-agent-profile-jason-heyward.html |access-date=November 29, 2015 |publisher=MLB Trade Rumors}} The Cardinals lost the National League Division Series to the Chicago Cubs, three games to one. After becoming a free agent for the first time in his career,{{Cite news |last=Galanis |first=Sam |date=November 10, 2015 |title=MLB free agent power rankings: David Price, Jason Heyward lead top 25 |work=NESN.com |url=http://nesn.com/2015/11/mlb-free-agent-power-rankings-david-price-jason-heyward-lead-top-25/ |access-date=November 10, 2015}} Heyward won his third Fielding Bible Award{{Cite web |last=Goold |first=Derrick |date=November 1, 2015 |title=Heyward wins Fielding Bible award while Molina left for the Gold |url=http://www.stltoday.com/sports/baseball/professional/birdland/heyward-wins-fielding-bible-award-while-molina-left-for-the/article_7692098f-1bbf-5edd-a89f-9fe26acf2a6b.html |access-date=November 1, 2015 |website=St. Louis Post-Dispatch}} and his third Gold Glove.{{Cite web |last=Miller |first=Doug |date=November 10, 2015 |title=Endless glove: Best D honored; more tonight |url=https://www.mlb.com/news/gold-glove-winners-announced/c-156972846 |access-date=November 10, 2015 |website=MLB.com}}

File:Jason Heyward on July 17, 2016 (2).jpg]]

On December 15, 2015, Heyward signed an eight-year, $184 million contract with the Cubs.{{Cite news |last=Gonzales |first=Mark |date=December 15, 2015 |title=Jason Heyward passionately signs up for Cubs' quest to win World Series |work=Chicago Tribune |url=http://www.chicagotribune.com/sports/baseball/cubs/ct-cubs-introduce-jason-heyward-20151215-story.html |access-date=December 16, 2015}} At the time of Heyward's signing, the contract was the largest player contract that had ever been signed by the Cubs.{{Cite web|url=https://www.bleachernation.com/cubs/2023/10/14/jason-heywards-finally-done/|title=Jason Heyward's $184M is Finally Coming off the Books After a Great Season in L.A.|website=bleachernation.com |last=Cerami |first=Michael |date=October 14, 2023}} During his tenure with the Cubs, Heyward's play did not reach the expectations created by his contract.{{Cite web|url=https://www.nbcsportschicago.com/mlb/chicago-cubs/heyward-says-ill-rock-that-badge-of-maligned-contract/334251/|website=nbcsportschicago.com|title=Heyward says 'I'll rock that badge' of maligned contract|date=September 30, 2022}}{{Cite web|url=https://www.yardbarker.com/mlb/articles/cubs_release_free_agent_bust_jason_heyward_with_one_year_left_on_deal/s1_13237_38120808|title=Cubs release free-agent bust Jason Heyward with one year left on deal|date=November 15, 2023|website=Yardbarker}}

One of Heyward's first acts after signing his contract was to pay for hotel suites large enough to accommodate teammate David Ross, his wife, and their three young children on all of the Cubs' road trips during the 2016 season. Ross, set to retire after the 2016 season, had been Heyward's teammate during his first three seasons in Atlanta, and Heyward considered him a key mentor in his early MLB career. In an interview with Bleacher Report, Heyward said,

I know how special it is to have teammates like he was my first three years in Atlanta. You don't take it for granted. I wanted to say thank you from the bottom of my heart, as a teammate and as a friend, for what he's done for me.{{Cite news |last=Miller |first=Scott |date=May 23, 2016 |title=Dream Team: A Week with Cubs' Modern Family Reveals Unmatched Off-Field Bond |work=Bleacher Report |url=http://bleacherreport.com/articles/2640789-dream-team-a-week-with-cubs-modern-family-reveals-unmatched-off-f |access-date=May 24, 2016}}

Heyward struggled in his first season with the Cubs in 2016, batting only .230 with 7 home runs and 49 RBIs; however, he did win his fourth Gold Glove that season.{{Cite web|url=https://www.cbsnews.com/chicago/news/cubs-anthony-rizzo-jason-heyward-win-gold-gloves/|title=Cubs' Anthony Rizzo, Jason Heyward Win Gold Gloves - CBS Chicago|date=November 8, 2016|website=www.cbsnews.com}}

In Game Four of the 2016 National League Division Series against the San Francisco Giants, with the Cubs holding a 2–1 series lead, Heyward reached on a bunt force out. He then moved to second on an errant throw and scored the go-ahead run on a Javier Baez single, sending the Cubs to the 2016 National League Championship Series.{{Cite web |last1=Haft |first1=Chris |last2=Muskat |first2=Carrie |date=October 11, 2016 |title=Cubs deliver Giant stunner, advance to NLCS |url=https://www.mlb.com/news/cubs-rally-to-defeat-giants-advance-to-nlcs-c205809290 |access-date=October 12, 2016 |website=MLB.com}}

On October 25, 2016, Heyward, along with teammates Dexter Fowler, Addison Russell, and Carl Edwards Jr., became the first African-Americans to play for the Cubs in a World Series game.{{Cite news |last=Collier |first=Jamal |date=October 25, 2016 |title=Fowler Cubs' first African-American in Series: Center fielder will be first up in Game 1; Heyward, Edwards, Russell also honored by distinction |work=MLB.com |url=http://m.cubs.mlb.com/news/article/206961888/dexter-fowler-set-for-history-in-world-series/ |access-date=October 25, 2016 |archive-date=October 26, 2016 |archive-url=https://web.archive.org/web/20161026080022/http://m.cubs.mlb.com/news/article/206961888/dexter-fowler-set-for-history-in-world-series/ |url-status=dead }} Heyward was credited with leading an inspiring players-only meeting during a 17-minute rain delay near the end of Game 7 of the 2016 World Series.{{Cite news |last=Armour |first=Nancy |date=November 3, 2016 |title=Jason Heyward's speech spurs Cubs during World Series Game 7 rain delay |work=USA Today |url=https://www.usatoday.com/story/sports/MLB/cubs/2016/11/03/world-series-championship-game-7-rain-delay-jason-heyward/93226544/ |access-date=November 3, 2016}} The Cubs eventually won the game 8–7 after 10 innings, which gave the franchise its first World Series championship in 108 years.{{Cite web |last1=Bastian |first1=Jordan |last2=Muskat |first2=Carrie |date=November 3, 2016 |title=Cubs are heavy wait champions! |url=https://www.mlb.com/news/chicago-cubs-win-2016-world-series-c207938228 |access-date=November 3, 2016 |website=MLB.com}} Heyward hit .104 during the 2016 playoffs. On November 9, Heyward became the first position player in Major League Baseball history to win three straight Gold Glove Awards with three different teams (Braves, Cardinals, and Cubs).{{Cite web |date=November 8, 2016 |title=Three Giants, two Cubs among winners of Gold Gloves |url=https://www.espn.com/mlb/story/_/id/18004040/gold-glove-awards-chicago-cubs-take-two-home-san-francisco-giants-win-three |access-date=November 9, 2016 |website=ESPN |agency=Associated Press}}

On May 8, 2017, Heyward went on the 10-day disabled list due to a sprained finger he suffered in a game against the Yankees three days prior.{{Cite web |last=Perkins |first=Owen |date=May 8, 2017 |title=Sprained finger sends Jason Heyward to DL |url=https://www.mlb.com/news/jason-heyward-on-dl-with-sprained-finger-c229076024/ |access-date=May 8, 2017 |website=MLB.com}} In late June, Heyward suffered a left-hand laceration while catching a foul ball in Pittsburgh and was unavailable to play in the next series of games.{{Cite web |last=Muskat |first=Carrie |title=Heyward out again, DL might be an option |url=https://www.mlb.com/news/hand-injury-keeps-cubs-jason-heyward-out-c237857060 |access-date=June 22, 2017 |website=MLB.com}}

Heyward chose "J-Hey" as his nickname for the Players Weekend during the 2017 season.{{Cite web |date=August 10, 2017 |title=MLB Players Weekend to showcase unique nicknames, colorful uniforms |url=http://chicago.suntimes.com/sports/mlb-players-weekend-to-showcase-unique-nicknames-colorful-uniforms/ |website=Chicago Sun-Times}} For the season, Heyward hit .259 with 11 home runs and 59 RBIs.

On May 8, 2018, Heyward again went on the disabled list due to concussion protocols after attempting a game-saving catch of a home run by William Fowler in the 14th inning.{{Cite web |last=Muskat |first=Carrie |date=May 18, 2018 |title=Cubs place Heyward on concussion DL |url=https://www.mlb.com/cubs/news/jason-heyward-injured-placed-on-concussion-dl/c-275828400 |access-date=July 16, 2018 |website=MLB.com}} On June 6, Heyward hit a walk-off grand slam home run with two outs in the bottom of the ninth inning to give the Cubs a 7–5 win over the Philadelphia Phillies.{{Cite web |date=June 6, 2018 |title=Heyward's walk-off grand slam |url=https://www.mlb.com/video/heywards-walk-off-grand-slam/c-2126932683 |access-date=July 16, 2018 |website=MLB.com}} At the All-Star break, Heyward had a .285 batting average with 78 hits in 274 plate appearances with six home runs and 41 RBIs, a .344 OBP and a .431 SLG.{{Cite web |title=Jason Heyward 2018 Batting Game Logs |url=https://www.baseball-reference.com/players/gl.fcgi?id=heywaja01&t=b&year=2018 |access-date=July 13, 2021 |website=Baseball-Reference.com |language=en}} Heyward ended the season with a .270 batting average, eight home runs, and 57 RBIs.

Heyward had a quality start to the season. He hit two home runs and stole two bases against the Milwaukee Brewers on April 6, becoming only the 18th player—and first Cub—to have a multi-homer, multi-steal game since 1901.{{Cite web |title=Player Batting Game Finder: In the Regular Season, since 1901, requiring Home Runs >= 2 and Stolen Bases >= 2, sorted by earliest Date. |url=https://stathead.com/tiny/g9nwc |access-date=April 15, 2021 |website=Stathead}} It was also his first multi-homer game as a Cub. On April 24, he hit a dramatic three-run home run late in the game to regain the lead in a 7–6 victory against the Los Angeles Dodgers. On May 8, Heyward hit a walk-off, solo home run against the Miami Marlins in the 11th inning, giving the Cubs a 3–2 win.{{Cite news |last=Bastian |first=Jordan |date=May 9, 2019 |title=2nd straight walk-off HR: This Cub takes turn |work=MLB.com |url=https://www.mlb.com/news/jason-heyward-hits-walk-off-home-run |access-date=July 25, 2020}} This was Heyward's third walk-off hit and second walk-off home run as a Cub. With that hit, he snapped a 1-for-20 slump.{{Cite web |last=Yellon |first=Al |date=May 9, 2019 |title=Cubs 3, Marlins 2: Jason Heyward walks it off |url=https://www.bleedcubbieblue.com/2019/5/9/18538037/cubs-marlins-jason-heyward-kyle-hendricks-mlb-scores |access-date=July 13, 2021 |website=Bleed Cubbie Blue |language=en}} For the season, Heyward hit .251 with 21 home runs and 62 RBIs.

In the pandemic-shortened 2020 season, Heyward batted .265/.392/.456 with six home runs and 22 RBIs in 50 games.{{Cite web |title=Jason Heyward 2020 Batting Game Logs |url=https://www.baseball-reference.com/players/gl.fcgi?id=heywaja01&t=b&year=2020 |access-date=July 13, 2021 |website=Baseball-Reference.com |language=en}}

In 2021, Heyward slashed .214/.280/.347 with eight home runs and 30 RBIs in 104 games.

On May 8, 2022, Heyward was placed on the injured list with a left quadriceps strain. He returned to the IL in late June.{{cite news |title=Cubs select of Narciso Crook from Triple-A Iowa, place of Jason Heyward on 10-day injured list |url=https://www.mlb.com/press-release/press-release-cubs-select-of-narciso-crook-from-triple-a-iowa-place-of-jason-hey |access-date=August 14, 2022 |work=MLB.com |date=June 30, 2022}}{{cite news |title=Lingering knee injury lands Cubs' Heyward on IL |url=https://www.nbcsports.com/chicago/cubs/cubs-jason-heyward-knee-il-narciso-crook-promoted |access-date=August 14, 2022 |publisher=NBC Sports |date=June 30, 2022}} He remained on the injured list through August. In August, Cubs general manager Jed Hoyer stated that the team would release Heyward at the end of the season.{{cite news |last1=Bastian |first1=Jordan |title='Emotional leader' Heyward, Cubs to part ways |url=https://www.mlb.com/news/cubs-to-part-ways-with-jason-heyward |access-date=August 14, 2022 |work=MLB.com |date=August 8, 2022}}{{cite news |last1=Rogers |first1=Jesse |title=Jason Heyward, despite another year left on contract, won't be back with Chicago Cubs in 2023, Jed Hoyer says |url=https://www.espn.com/mlb/story/_/id/34371593/jason-heyward-another-year-left-contract-back-chicago-cubs-2023-jed-hoyer-says |access-date=August 14, 2022 |work=ESPN.com |date=August 8, 2022}} In 48 games for the Cubs, Heyward batted .204/.278/.277 with one home run and 10 RBI. He was officially released by Chicago on November 14, 2022,{{Cite web|title=Jason Heyward officially released by Cubs on Monday|url=https://wgntv.com/sports/cubs/jason-heyward-officially-released-by-the-cubs-on-monday/amp/|access-date=July 14, 2023|website=wgntv.com|date=November 14, 2022 |language=en}} despite the fact that the Cubs still owed him a salary of $22 million for the 2023 season.{{cite web | last=Goldberg | first=Rob | title=Jason Heyward Released by Cubs With $22M Remaining on Contract | website=Bleacher Report | date=2022-11-14 | url=https://bleacherreport.com/articles/10049124-jason-heyward-released-by-cubs-with-22m-remaining-on-contract | access-date=2024-11-01}}{{Cite web|url=https://www.yardbarker.com/mlb/articles/cubs_release_free_agent_bust_jason_heyward_with_one_year_left_on_deal/s1_13237_38120808|title=Cubs release free-agent bust Jason Heyward with one year left on deal|date=November 14, 2022|website=Yardbarker}}

During his seven-year stint with the Cubs, Heyward batted .245,{{Cite web|url=https://www.mlbtraderumors.com/2023/11/2023-24-top-50-free-agents-with-predictions.html|title=2023-24 Top 50 Free Agents With Predictions|date=November 6, 2023|website=MLB Trade Rumors}} hitting 62 home runs in 2,522 plate appearances.{{Cite magazine|url=https://www.si.com/mlb/2022/08/09/cubs-plan-to-release-jason-heyward-from-final-year-of-deal|title=Cubs Plan to Release Jason Heyward From Final Year of Deal|first=Jelani|last=Scott|date=August 8, 2022|magazine=Sports Illustrated}} In December 2022, The Sporting News included Heyward's eight-year, $184 million contract with the Cubs on its list of the top 15 worst MLB free-agent contracts of all time.{{Cite web|url=https://www.sportingnews.com/us/mlb/list/worst-mlb-free-agents-signings-josh-hamilton-carl-pavano-jason-bay-carl-crawford-albert-belle/zaaj9h66jdc41an4uaou11u0n|title=The 15 worst MLB free-agent signings of all time|date=December 7, 2022|website=www.sportingnews.com}}

On December 8, 2022, Heyward signed a minor league contract with the Los Angeles Dodgers that included an invitation to major league spring training.{{cite web|url=https://www.mlbtraderumors.com/2022/12/dodgers-sign-jason-heyward.html|title=Dodgers Sign Jason Heyward To Minor League Deal|work=MLB Trade Rumors|first=Steve|last=Adams|date=December 8, 2022|accessdate=December 8, 2022}} He made the Dodgers' Opening Day roster,{{cite web | title=Dodgers' Jason Heyward: Confirmed for Opening Day roster | website=CBSSports.com | date=2023-03-23 | url=https://www.cbssports.com/fantasy/baseball/news/dodgers-jason-heyward-confirmed-for-opening-day-roster/amp/ | access-date=2024-11-01}} reworked his swing,{{Cite web|url=https://www.si.com/mlb/dodgers/news/dodgers-news-jason-heyward-shares-appreciation-for-teammates-in-award-win-sm1970|title=Dodgers News: Jason Heyward Shares Appreciation for Teammates in Award Win|first=Sarah|last=Morris|date=September 25, 2023|website=SI.com}} accepted a platoon role,{{cite web | last=Plunkett | first=Bill | title=Jason Heyward's impact on Dodgers has not gone unnoticed | website=Orange County Register | date=2023-10-02 | url=https://www.ocregister.com/2023/10/02/jason-heywards-impact-on-dodgers-has-not-gone-unnoticed/ | access-date=2024-11-01}} and enjoyed a resurgent season.{{Cite web|url=https://www.si.com/mlb/dodgers/news/dodgers-news-jason-heyward-knew-he-could-revitalize-career-in-la-ml0802|title=Dodgers News: Jason Heyward Always Believed He Could Make An Impact For LA|first=Matt|last=Levine|date=October 3, 2023|website=SI.com}}{{Cite web|url=https://www.si.com/mlb/cubs/news/former-chicago-cubs-jason-heyward-among-top-50-free-agents-matt9|title=Former Chicago Cubs Outfielder Among Top 50 Free Agents|first=Matthew|last=Postins|date=November 3, 2023|website=SI.com|access-date=November 25, 2023|archive-date=November 25, 2023|archive-url=https://web.archive.org/web/20231125051121/https://www.si.com/mlb/cubs/news/former-chicago-cubs-jason-heyward-among-top-50-free-agents-matt9|url-status=dead}} Heyward played in 124 games, batting .269 with 15 homers and 40 RBI. Following the season, Heyward received the Roy Campanella Award, an award that is given by Dodgers players and coaches to the most inspirational Dodger on the team.

On December 6, 2023, Heyward signed a one-year, $9 million contract to return to the Dodgers.{{cite web | title=Jason Heyward and Los Angeles Dodgers finalize $9 million, 1-year contract | website=USA TODAY |agency=Associated Press| date=2023-12-06 | url=https://www.usatoday.com/story/sports/mlb/2023/12/06/jason-heyward-and-los-angeles-dodgers-finalize-9-million-1-year-contract/71827568007/ | access-date=2024-11-01}} In 63 games for them in 2024, he batted .208 with six home runs and 28 RBI. He was designated for assignment on August 22, two days after he hit a pinch-hit go-ahead three-run home run in his final at-bat for the Dodgers.{{cite web|url=https://www.mlb.com/dodgers/news/jason-heyward-designated-for-assignment-by-dodgers|title=Dodgers DFA Jason Heyward, activate Chris Taylor|work=mlb.com|first=Jason|last=Foster|date=August 22, 2024|accessdate=August 22, 2024}}{{cite news |last1=Gonzalez |first1=Alden |title=Veteran Jason Heyward DFA'd by Dodgers amid roster crunch |url=https://www.espn.com/mlb/story/_/id/40954421/veteran-jason-heyward-dfad-dodgers-amid-roster-crunch |access-date=August 23, 2024 |work=ESPN.com |date=August 22, 2024}} The Dodgers released him on August 26.{{cite web|url=https://www.mlbtraderumors.com/2024/08/dodgers-release-jason-heyward.html|title=Dodgers Release Jason Heyward|work=MLB Trade Rumors|first=Anthony|last=Franco|date=August 26, 2024|accessdate=August 27, 2024}}

On August 29, 2024, Heyward signed a one-year, major league contract with the Houston Astros.https://x.com/astros/status/1829248184222134283 During his debut as an Astro, Heyward hit a key two-run double that spearheaded a 6–3 win versus the Kansas City Royals.{{Cite web|last=Young|first=Matt|date=August 29, 2024|title=Astros 6, Royals 3: Houston has big eighth inning to come back and beat Kansas City|url=https://www.houstonchronicle.com/sports/astros/article/astros-royals-game-recap-19730687.php|access-date=August 29, 2024|website=Houston Chronicle}}

On September 24, 2024, the Astros clinched their fourth straight American League (AL) West Division title with a 4–3 win over the Seattle Mariners. Heyward made a jumping catch into the scoreboard to take away a hit in the top of the fifth inning and hit a two-run home run in the bottom half of the inning to give the Astros a lead they would not relinquish.{{Cite news |last=McTaggart |first=Brian |date=September 24, 2024 |title=Division dynasty continues: Resilient Astros grab 4th straight AL West title |url=https://www.mlb.com/news/astros-win-2024-al-west-title |access-date=September 25, 2024 |website=MLB.com}} As a member of the Astros, Heyward appeared in 24 games, batting .218/.283/.473 in 61 plate appearances, 2 doubles, 4 home runs, 9 RBI, and 1 stolen base. He played 16 games in right field, 8 in left field, and 2 in center field. Heyward appeared in both games of, and was 0-for-3 in, the American League Wild Card Series (ALWCS), which was swept by the Detroit Tigers. Following the season, he elected free agency.{{cite news |last=Kawahara |first=Matt |url=https://www.houstonchronicle.com/sports/astros/article/free-agency-alex-bregman-justin-verlander-kikuchi-19872362.php |title=Alex Bregman, Justin Verlander, Yusei Kikuchi head list of 8 Astros on MLB's free-agent market |work=Houston Chronicle |date=November 1, 2024 |access-date=November 3, 2024}}

On February 11, 2025, Heyward signed a one-year, $1 million contract with the San Diego Padres.{{Cite web |date=2025-02-08 |title=Padres Sign Former Dodgers, Braves All-Star Outfielder in Big Free Agent Move |url=https://www.si.com/mlb/padres/san-diego-padres-news/padres-sign-former-dodgers-braves-all-star-outfielder-in-big-free-agent-move-01jkhz4b6xgh |access-date=2025-02-08 |website=San Diego Padres On SI |language=en-US}}

In September 2012, Piedmont Henry Hospital in Stockbridge, Georgia, selected Heyward as one of ten representatives for their Real Men Wear Pink campaign against breast cancer. He stated at the time that one of his grandmothers was battling the condition but had improved and that her battle was an inspiration for him to participate.{{Cite web |last=Smith |first=Jason A. |date=September 26, 2012 |title=Heyward headlines 'Real Men' campaign |url=http://www.henryherald.com/news/2012/sep/26/heyward-headlines-real-men-campaign/?community |access-date=January 16, 2015 |website=Henry Daily Herald}}

Heyward's brother, Jacob, is a coach in the San Francisco Giants organization.{{Cite web |last=Sherman |first=Mitch |date=June 16, 2015 |title=Sherman: Heyward comes through in starring role for Miami |url=https://www.espn.com/college-sports/baseball/cws/story/_/id/13086622 |access-date=July 13, 2021 |website=ESPN.com}} Jacob Heyward was drafted by the Atlanta Braves out of high school in the 2013 MLB Draft and by the Giants in the 2016 MLB Draft.{{Cite web |last1=Single |first1=Eric |last2=Bowman |first2=Mark |date=June 8, 2013 |title=Braves grab Heyward's brother in 38th round |url=https://www.mlb.com/news/braves-grab-heywards-brother-in-38th-round/c-50047054 |access-date=July 13, 2021 |website=MLB.com}}{{Cite web |last=Haft |first=Chris |date=June 12, 2016 |title=Giants draft Heyward's brother on own merits |url=https://www.mlb.com/news/giants-draft-jason-heyward-s-brother-jacob-c183577550 |access-date=July 13, 2021 |website=MLB.com}}

Heyward is married to Vedrana Heyward.{{Cite instagram |user=jheylove22 |postid=CRUc-ZHsNBa |date=July 14, 2021|access-date=July 15, 2021 |link=https://www.instagram.com/p/CRUc-ZHsNBa/ |title=Wife 🤍 }}{{Cite instagram |user=veeheyward |postid=CMhdz32n2xY |date=March 17, 2021|access-date=July 15, 2021 |link=https://www.instagram.com/p/CMhdz32n2xY/ |title=•LIFE• 🧿}} Their son was born in March 2022.{{Cite web |url=https://twitter.com/cubszone/status/1500602682507251719 |title= Jason Heyward announced that he and his wife Vee have welcomed a baby boy into the world.|access-date=March 21, 2022 |website=Twitter |language=en}} They own a $5.9 million mansion in the Gold Coast neighborhood of Chicago.{{cite web | last=Goldsborough | first=Bob | title=Chicago Cubs right fielder Jason Heyward buys 6-bedroom Gold Coast mansion for $5.9 million | website=Chicago Tribune | date=2020-11-23 | url=https://www.chicagotribune.com/2020/11/23/chicago-cubs-right-fielder-jason-heyward-buys-6-bedroom-gold-coast-mansion-for-59-million/ | access-date=2024-10-26}}

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• List of Major League Baseball career putouts as a right fielder leaders
• List of Major League Baseball players with a home run in their first major league at bat

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• {{note label|DRS|a|a}}{{note label|DRS|a|b}} Developed by the organization that awards The Fielding Bible, defensive runs saved (DRS) measures a player's total defensive plays made in terms of numbers of runs above or below what the average player at that position made. A calculation system computes the number of plays made league-wide at each position and a plus-minus total rating for each player compared to a league-average player. For example, if Heyward made a play that only 20% of right fielders would make, he was credited with .8 points – or, 1 point minus .20. If he failed to make a play that 75% of right fielders made, then .75 points were subtracted from his score.{{Cite web |title=Sabermetrics Library: DRS |url=http://www.fangraphs.com/library/defense/drs/ |access-date=November 30, 2013 |publisher=Fangraphs}}

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{{Commons category|Jason Heyward}}

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• [http://mlb.mlb.com/mlb/minorleagues/prospects/y2009/profile.jsp?t=p_top&pid=518792 MLB Top 50 prospects – Scouting Report]
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