Jason Heyward

At 34 years old, Jason Heyward has this physical status:

Jason Alias Heyward (born August 9, 1989), nicknamed "J-Hey" is an American professional baseball right fielder for the Chicago Cubs of Major League Baseball (MLB).

Originally the Atlanta Braves' first-round selection in the 2007 MLB draft from Henry County High School in Georgia, he began his minor league career at age 17.

Heyward soon became one of the top-rated prospects in all of baseball for batting, speed, and defense, and debuted in MLB as Atlanta's starting right fielder on Opening Day 2010.

There, he played until being traded to the St. Louis Cardinals after the 2014 season.

Standing 6 feet 5 inches (1.96 m) tall and weighing 245 pounds (111 kg), he throws and bats left-handed.

He has worn uniform No. 22 throughout his major league career in honor of a high school friend and teammate who died in a traffic collision. A three-time minor league All-Star game selection, Baseball America selected Heyward as the Braves' top overall prospect in 2007 and the organization's best power hitter; it cited Heyward as having the best strike zone discipline and excelling at multiple other skills.

In 2009, he won a Minor League Player of the Year Award from both Baseball America and USA Today.

That year, he batted .323 with 17 home runs (HR), 63 runs batted in (RBI), a .408 on-base percentage, and a .555 slugging percentage over 99 games.

A consensus number-one MLB prospect entering the 2010 season, Baseball America, Keith Law of ESPN.com, and Jonathan Mayo of MLB.com all listed Heyward as baseball's top prospect.After making his MLB debut for Atlanta in 2010, Heyward was named to the National League (NL) All-Star team and finished second in the NL Rookie of the Year Award.

Baseball America named him their MLB Rookie of the Year.

Injuries limited his playing time in 2011 and 2013.

With a breakout season in 2012, he hit 27 home runs with 82 RBI and 21 stolen bases while finishing tenth in the NL in runs scored with 93.

Also recognized for his defense including coverage in the deepest parts of right field, he won both the Fielding Bible and NL Gold Glove Awards for right fielders in 2012, 2014, 2015, 2016 and 2017 and Wilson's MLB Defensive Player of the Year in 2014.

He is widely regarded as one of the best outfield defenders in baseball.

Personal life

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 one of his grandmothers was battling the condition but had improved, and that her battle was an inspiration for him to participate.

Heyward's brother, Jacob, is an outfielder in the San Francisco Giants organization. Jacob Heyward was drafted by the Braves out of high school in the 2013 MLB Draft and the San Francisco Giants in the 2016 MLB Draft.

Heyward is married to Vedrana Heyward. Their son was born in March 2022. They own a $5.9 million mansion in the Gold Coast neighborhood of Chicago.

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Early life and amateur career

Jason Heyward, the son of Dartmouth graduates, was born in Ridgewood, New Jersey, on August 9, 1989. Eugene's father, Eugene, is from Beaufort, South Carolina, and Laura, her mother, hails from New York City; they met at Dartmouth. Eugene played basketball and majored in electronics, while Laura studied French. Kenny Washington, Eugene's uncle, played basketball for two John Wooden-led NCAA championship UCLA teams in 1964 and 1965. Jacob (b. ) is Jason's younger brother. (1996), a graduate of the University of Miami and played baseball for the Hurricanes, and was a member of the University of Miami. Jacob was drafted by the San Francisco Giants in 2016 and has played in the minors for the first time ever.

About the time he was born, the Heywards began to move to the Atlanta metropolitan area shortly after. Jason played and demonstrated considerable promise in baseball from an early age. He competed for a national championship before he turned ten. Eugene was a source of both his sons' and daughters' love of baseball. He committed himself to bringing them all tournament and competition possible in the family Chevrolet Suburban, which traveled hundreds of thousands of miles between the events and his 90-minute commute to and from Robins Air Force Base to the south in Houston County.

Although his father emphasized that working hard and approaching the game with discipline were vital, he also stressed that baseball was to be enjoyable, above all else. Heyward has followed this same philosophy throughout his youth and professional careers. One tournament in which he competed 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, just south of Atlanta. Heyward played basketball in his youth for a brief period, but at his father's behest, he concentrated solely on baseball in high school. An Associated Press reporter learned from a varsity coach that Heyward's early batting practice exploits led to the death of an oak tree in deep center field at the high school playing field in February 2010.

In the Georgia Class AAAA baseball championships against upcoming Major League Baseball (MLB) catcher Buster Posey of Lee County High during Heyward's sophomore year, Henry County won two of the best-of-three series. In the first game, Posey was actually the starting pitcher as Henry Country defeated Henry Country 2–1. In Game 2, Heyward scored a game-tying 400 feet (120 m) home run to cap an eight-run comeback, but Lee County defeated Lee County 14-10. In a 16–14 draw, Heyward's three-run single was the game and series champion. He also helped lead the Henry County High Warhawks to the state championship during his junior season. He batted.520 with eight home runs (HR) and 29 runs batted in (RBI).

Andrew Wilmot, one of Heyward's closest friends and teammates from the 2005 AAA Georgia state championship team, died in a traffic crash while attending college. Wilmot was a catcher who wore the uniform number 22, the number Heyward would later wear in his major league career to honor him. Tammie Ruston, Wilmot's mother, was a high school literature instructor in Heyward in his senior year.

Multiple colleges expressed curiosity in recruiting Heyward, including UCLA, which offered a full ride scholarship due in part to the family connection. Heyward was also very interested in Clemson and Georgia Tech. The Atlanta Braves had followed and scouted him for years, although they were trying to mask their elation. In the 2007 Major League Baseball draft, they ranked him 14th overall pick. Heyward, who signed a National Letter of Intent with UCLA, opted for professional baseball over college and signed a deal with them worth $1.7 million, much more than MLB's slot recommendation of $1.53 million on the following August 12. It was the same as Travis Snider's 2006 14th-slot purchase.

Professional career

Heyward began his playing career in Minor League Baseball in the Braves' system at age 17. In 2007, he competed for both the Gulf Coast League Braves and the Danville Braves of the Appalachian League. In his first professional game, he came home. He batted.302 in 12 minor league contests in 2007 with one home run and six runs batted in (RBIs). He has spent time in Rome in the South Atlantic League (SAL) and Advanced-A Myrtle Beach of the Carolina League.

Heyward batted.330 (33-for-100) in April 26 games to go with three home runs, 16 RBI, and seven stolen bases, beginning the season with Rome. He was later named Player of the Month by the club's Player of the Month. He batted over.300 in May,.315 in June,.315 in July, and.386 in August, but he didn't batted over.345 in July. He went on a high 11-game streak from May 7 to 19, batting.386 with five doubles (2B) and two home runs. On June 30, he hit Columbus for three runs, with three hits, including a home run.

Heyward wrote 42 multi-hit games, two of which were four-hit games, while playing for Rome. In nine offensive categories for the club, he came in third place. He batted.351 (33-for-94) off left-handed pitchers (LHP) with four home runs and.315 (112-for-355) against right-handed pitchers (RHP). His season with the club included a.323 batting average (third in the SAL),.388 on-base percentage (OBP, fourth), 88 runs scored (fifth), and a 0.84% on-base plus slugging percentage (OPS, sixth).

On August 25, the Braves sent him to Myrtle Beach, where he appeared in seven other games. His average was.182. He had four hits in 22 A.B. He went for four RBIs there. His.316 batting average led the Braves' minor league system, ranked second, 29 doubles, and 149 hits, while six triples and.854 OPS were ranked sixth, with 91 runs ranked fifth, 29 doubles, and 149 hits all ranked fifth, respectively. In addition, he has stolen 15 bases.

More awards have followed the 2008 season. Heyward was named as the South Atlantic League's Most Valuable Prospect, Top Batting Prospect, and Most Exciting Player in the South Atlantic League. He was also a MLB All-Star for the entire minor leagues, Mid- and Post-Season All-Star, and the Braves' second-best prospect. He was voted the third best overall minor league prospect by MLB.com. He was named the top corner outfield prospect in the minor leagues and the third-overall minor-league prospect, according to ESPN.com.

Since 2009, Heyward, Myrtle Beach, Heyward, has been promoted to Double-A Mississippi and Triple-A Gwinnett. He appeared in 42 of the 49 games at Myrtle Beach and hosted 16 multi-hit contests. On May 18, he earned six hits in 23 at-bats (.261), with three home runs and five RBI. He suffered with an oblique injury in late May, causing him to miss multiple games. He was a member of the Carolina League All-Star team but he missed the game due to an oblique injury. He was in the All-Star Futures Game at Busch Stadium, where he scored one hit in two at-bats. Through July 4, he had a nine-game winning streak.

Heyward was sent by the Braves to Mississippi on July 4, where he lasted the streak to 13 games (.352) with four doubles and 14 RBI. With four hits on July 16, he set a new career record. He had 34 hits, 14 walks, 11 doubles, three home runs, 19 RBI, and a 1.230 OPS in 22 games for that month. The Braves named him their Mississippi Player of the Month. His OBP and 1.057 OPS were among his totals with the club. He appeared with the Gwinnett Braves of the Triple-Age in the International League from September 5 to 7. He also appeared in four games with the Peoria Sacrament of the Arizona Fall League (AFL), totaling four hits in 14 AB and three 2B.

With 17 home runs and 10 steals, including high numbers in OBP (.408), slugging percentage (SLG,.555), and OPS (.963), he batted.323 in 99 games, including high numbers in OBP (.408), slugging percentage (SLG,.555), and OPS (.963), while driving in 63 runs. In several offensive categories, including second in runs, third in average, home runs, and OPS, sixth in hits (117) and RBI, and tied for seventh in doubles (25). He had a strong hitting ability against both RHP and LHP. Heyward scored.339 in 112 AB against LHP and.316 against RHP in 2009. He had batted.335 with six home runs against left-handed pitchers and.313 with 23 home runs against right-handed pitchers during his minor league career from 2009 to.313 with 23 home runs against right-handed pitchers.

Both Baseball America and USA Today selected him as their Minor League Player of the Year for September. Heyward was rated as the top prospect in baseball by a consensus number one in the 2010 season, Baseball America, Keith Law of ESPN.com, and Jonathan Mayo of MLB.com; BA ranked him ahead of Stephen Strasburg and Giancarlo Stanton. In addition, Baseball America named him the top prospect in both the Southern and Carolina Leagues, the Top Batting Prospect in all of Double-A, and the Most Exciting Player in Single-A. He received the Hank Aaron Award from the Braves' organization (not to be confused with MLB's Hank Aaron Award), which is given annually to the best offensive player in the Braves organization.

Baseball America also ranked parts of Heyward's game sets as the best in the Braves minor leagues, including Best Strike-Zone Discipline (three times), Best Defensive Outfielder (once), and Best Outfield Arm (once). Before the 2010 season, the Braves welcomed Heyward to their 40-man roster.

The Braves welcomed Heyward to spring training in March 2010 after a quick climb through the minor leagues. His hitting continued to attract interest, with his "rockets" regularly hitting "walls and fences, prompting boss Bobby Cox to make him a regular in the lineup. He claimed that the balls struck off Heyward's bat had a different, more pronounced sound. Reggie Jackson, a New York Yankees special assistant, agreed, describing the appearance as "stereo" while everyone else was "in AM." Heyward's first home runs at the Champion Stadium training facility in Lake Buena Vista, Florida, were recorded. In the parking lot, one crashed a Coca-Cola truck and another broke the sunroof Atlanta Braves assistant general manager Bruce Manno's car. He was first given his uniform number 71. He called the team for and received number 22 at the end of spring training. He wore one of his jerseys with the number 22 to Ruston to show that he honoured her son, which prompted an emotional reaction from her.

Shirts depicting his nickname, "The J-Hey Kid," were in high demand by now, even before he played his first official big league game. Fans and analysts have speculated about a future Hall of Fame career, including Darryl Strawberry, Willie McCovey, and Willie Mays among other items. In fact, Mays' nickname, "The Say Hey Kid," was derived from his nickname, "The J-Hey Kid." The Braves announced Heyward on March 26, after leading the team in on-base and slugging numbers in spring training.

Eugene Heyward bought 60 tickets in advance of his son's MLB debut against the Chicago Cubs on April 5. Ruston was also on hand in #22 jerseys from Heyward's #22 jersey. Heyward's first MLB appearance – and first swing at an MLB pitch – was his first run at a baseball park, offsetting starter Carlos Zane. Ruston was sitting in the right-field seats where the ball was landed. Heyward was the fifth player in Braves history to reach a home run in his first major league at-bat, and the 11th in franchise history to do so in his MLB debut, following Jordan Schafer, who did it last year.

Heyward soared to the hype in Atlanta's first 50 games, hitting 10 home runs and a.404 OBP and.596 slugging percentage. In both April and May, he was named National League (NL) Rookie of the Month. However, after suffering a thumb injury while sliding in May, he missed playing time. After returning later in the season, his results dropped, and consistency was elusive. He was selected as a starter for the NL All-Star squad, but he was unable to participate due to his thumb injury.

He became the first Brave to do so since Rafael Furcal, who did it more than ten years ago, after stealing home in a double robbery against the Washington Nationals in the first inning on July 28. On August, Heyward's first MLB multi-home run game and career highs in hits and runs scored with four each was defeated by a 16–5 victory over the Cubs. Heyward batted.266 with a.381 OBP and.396 SLG in the final 112 games of the season. His postseason debut against the San Francisco Giants was on October 7 in the National League Division Series (NLDS). With two strikeouts, Heyward was hitless in three at bats. San Francisco defeated Atlanta after collecting just two hits in the series, including one that was named after.

Heyward's first major league season featured a.277 average, 393.393 on-base percentage, 18 home runs, 29 doubles, 91 bases on balls, and 83 runs scored in 142 regular season games. In both OBP and walks, he came in fourth overall in the NL. He had been toting base for 36 games in a row. His OBP was the second-highest in major league history for a rookie aged 20 years or younger, after Ted Williams and before Frank Robinson, and he finished 30th in all MLB history counting rookie seasons. Heyward was named the Sporting News NL Rookie of the Year, Baseball America's MLB Rookie of the Year, an outfielder on the magazine's All-Rookie Team, and the top-five's Major League Rookie All-Star Team, recipient of several major awards, as the recipient of several major awards. In the NL Most Valuable Player (MVP) award balloting, he came in second second, second to Posey for the NL Rookie of the Year award and 20th.

Heyward's second MLB season began in a way that recalled the high hopes from his rookie season, but injuries eventually pushed the season's second season to a halt. He was diagnosed with a degenerative disorder in his lower back in the spring. In his first at-bat of the season, Liván Hernández started with a home run in his first at-bat of the season on March 31, 2011. In his first major league at-bat on opening day, he became just the second player after Kazuo Matsui, and the same follows year. Since being drafted in 2007, Heyward's third game of the season was also the third time the player was homered in his first game of the season.

In a back-and-forth game with the Giants on April 24, he struck a go-ahead home run off relief pitcher Jeremy Affeldt to win by 9–6, ten-inning victory. He hit.400 with three home runs and a.714 slugging percentage in the month's final eight games. Heyward's OPS hit seven home runs in the month of April. Heyward resigned from CSE after being represented by Victor Menocal from Career Sports Entertainment (CSE) until Menocal resigned from CSE, according to reports on May 6, who revealed his agent to Casey Close.

Heyward suffered with lingering shoulder pains from the start of spring training. The Braves undertook a magnetic resonance imaging (MRI) scan on May 12 after collecting only four hits in 41 at-bats in May, revealing an inflamed rotator cuff but no structural damage. He rested and received a cortisone injection, but the injury was exacerbated during batting practice days later. On May 22, the Braves placed him on the disabled list (DL). Jones, a teammate, suffered with his injuries after not playing through his illness, joined him next month; Jones said, "I think where Jason might have erred was the remark made" at the end; "I'm not coming back until it doesn't hurt anymore." Jason is a genius, and Jason at 80 percent is a natural performer, and Jason at 80 percent is higher than a majority of players in this league." Jones later explained that he reassured Heyward over a phone call that he did not intend to misrepresent Heyward's attempts to recover.

Heyward came from the DL with increased difficulty in order to propel the ball while batting. Heyward's first home run against the Baltimore Orioles on July 1 was his first home run since April 29 against the St. Louis Cardinals, a total of 104 at-bats. However, he had only four home runs from the beginning of April to August 11. His walking rate also dropped from 14.6 percent the year before to 10.7 percent. His line drive rate in that time decreased from 17.8 to 13.9% and one-quarter of his balls hit in the air were infield pop-ups, relative to eight percent the year before. On August 23, he scored his first grand slam during a game against the Chicago Cubs.

The Braves were the NL wild card leader until the end of August. On the other hand, the Cardinals overcame a 10+1,2 game deficit for the wild card position by winning 20 of their final 28 to ban the Braves from the playoffs, igniting one of the greatest late-season flops in MLB history. Heyward's overall results dropped off from his rookie season after suffering from a shoulder injury from the start of the season. His batting average dropped 50 points to.227; his other contributions, which included 14 home runs, 42 RBI, 18 doubles, and nine stolen bases in 128 games, were also declining. He batted.240 against right-handed pitchers, compared to 192 against left-handers.

Heyward took additional measures in his preseason preparations to reverse the season's lack in results. Following the shoulder injury, he streamlined his swing to avoid unhealthy habits that had been instilled. He changed his diet to include more fruits, chicken, and fish. He also took part in physical therapy to build the shoulder and fought for a leaner weight, going from 256 pounds (116 kilograms) to 235 pounds (107 kg). He began the 2012 season slowly. However, Lance Lynn's bases loaded double on May 13 off Lance Lynn was the game-winning run as the Braves defeated the Cardinals 7–4.

His output in June increased in June after he had a.233 batting average through May. On June 7, he played his first multi-HR game of the season and second of his career, leading to an 8–2 victory over the Marlins. With six home runs and a 1.080 OPS, he batted.353 in March of this year. On June 19, he had four outfield assists, one of which had Mark Teixeira out at home plate, giving the New York Yankees a 4–3 win.

He launched two home runs for his third appearance – and second at Yankee Stadium – in a double-HR game. Nine home runs between the two clubs were tying a Yankee Stadium record, as well as the original 1923 version. He received his first NL Player of the Week Award this week, which was June 24. He batted a league-leading.522 (12-for-23) and 1.130 slugging percentage in six interleague games. His three home runs, 12 hits, 26 total bases, and nine runs tied for the league lead. He has also played three multi-hit games and five RBI.

Heyward hit.455 (20-for-44) and homered four times during his 12-game streak that spanned June 13-27. One hit during that streak was a single on June 16, bringing an end to Jason Hammel's no-hit chance in the seventh inning and leaving him a one-hit complete game shutout in the Orioles' 5–0 win. On Monday, Heyward's home run in an 8–2 victory over the Marlins brought an end to Atlanta's streak of 16 losses.

Heyward's first two lifetime defensive accolades for right fielders: the singular MLB Fielding Bible Award and his first NL Rawlings Gold Glove Award are both awarded this year. His batting average in 158 games was.269, with career highs of 27 home runs, 82 RBI, 93 runs scored, 158 runs scored, six triples, and 21 SB. He batted.300 (105-for-350) against right-handers, but left-handers only.224 (53-for-237) against left-handers. It was the second time he was considered in the NL MVP balloting, placing him second in second place, finishing tied for 28th.

The Braves avoided arbitration with Heyward for the first time since being denied arbitration in 2013, agreeing to a one-year, $3.65 million contract. Justin and B. J. Upton, who were just recently signed, were tagged as a part of the outfield, and with whom he would not play until being traded after the 2014 season. On April 22, he was admitted to the 15-day disabled list after an appendectomy. He batted.142 (15-for-106) in his first 31 games of the season, with two home runs and eight RBI. In an 8–5 victory over the Dodgers on May 17, he recovered from an appendectomy and went 2-for-4. San Diego defeated San Diego on June 10, his first multi-HR game of the season.

Heyward batted.305 in 37 games following the All-Star break, with an OBP of.397 and an OPS of.932. With nine doubles, seven home runs, and 17 RBI, he had 40 hits in 131 at-bats, including nine doubles, seven home runs, and 17 RBI. He batted.457 OBP, six doubles, five home runs, and five home runs in a 19-game stretch from July 28 to August 17, four as a leadoff hitter with 15 RBI, eight BB, and 23 runs scored. Against Washington, he scored his second multi-HR game of the season on August 17. His.348 batting average (23 hits in 66 AB) ranked ninth in the NL in August.

On August 21, New York Mets pitcher Jon Niese struck Heyward in the chest with a pitch, breaking his jaw in two places. He underwent surgery, which needed the inserting of two plates, and returned on September 20. Heyward's protective shield was attached to the right side of his batting helmet. In a 9-5 victory over the Chicago Cubs, he came out and walked.

Heyward set career highs against Philadelphia on Friday, four extra-base hits, and tied for the third straightaies. He also hit his third and second of the season in his second appearance – leadingoff home runs. He made a.333 (38-for-114) clip in his last 31 games of the season, beginning July 28. He batted.322 (38-for-118) in 30 games as a leadoff hitter in 30 games. Heyward appeared in 104 total games, hitting.254 with 14 home runs, 22 2B, 38 RBI, 67 runs scored, and two stolen bases after two stints on the DL. In the games in which he appeared, the Braves led him to 71–33.

On February 4, 2014, the Braves bought Heyward's last arbitration-eligible years out of service, deciding on a two-year, $13.3 million contract. His coverage in the right field has greatly increased, as shown by increased defensive runs saved (DRS) overall, making him one of the top defensive outfielders in the league. He recorded 16 DRS through May 19, equaling three of his previous four seasons totals. According to Inside Edge (IE) graph, Heyward had missed a total of nine in 358 innings; all nine were rated with a 10% or lower chance of being caught. Mike Trout's catch in motion, one tumbling on a sinking line drive and one racing and leaping at the warning track, all contributed to a 7–3 victory over the Los Angeles Angels of Anaheim on June 15. Heyward also has a home run.

He appeared in 149 games as the Braves' primary leadoff hitter,.351 on-base percentage, 74 runs scored, 11 home runs, 20 stolen bases, and 20 stolen bases. Caught stealing just four times, his 83.3 percent success rate placed him fifth in the Netherlands. Heyward's defensively had a standout season. In 149 games in right field, he led the NL at his best putouts (365), assists (nine), field factor per nine innings (2.9%), and total zone runs (30). He was fifth in assists, third in range factor per game, and second in putouts and field percentage among all NL outfielders.

Heyward also ranked fourth in the league with 2.8 defensive wins over replacement (dWAR) and led all MLB players with 32 total DRS, according to Baseball-Reference.com. He earned 40 bases on deep-hit balls, the best work of his career, and led all MLB outfielders. Heyward received numerous accolades, including his second of both the Rawlings NL Gold Glove Award and the Fielding Bible Award for right fielders, the latter of which he received unanimously. Wilson Sporting Goods named him their MLB Defensive Player of the Year and Overall MLB Defensive Player of the Year.

The Braves and pitcher Jordan Walden for pitchers Shelby Miller and Tyrell Jenkins were traded by the St. Louis Cardinals on November 17, 2014, to replace their former right fielder and top prospect Oscar Taveras, who died in a car accident a month earlier. Heyward gave Cardinals manager Mike Matheny, who wore uniform #22 and had previously done so for the majority of his playing career, his number. Andrew Wilmot, Heyward's uncle, is honoured on this number. Heyward released a tweet thanking the Atlanta Braves team and fans for their continued help after the trade was announced.

Heyward appeared in his first game against the Chicago Cubs on April 5, 2015, five years to the day of his MLB debut. In a 3–0 victory, he had three hits, two doubles, and a stolen base. Busch Stadium defeated the Cincinnati Reds 5–2 in his first home run as a Cardinals player on April 18. After making uncharacteristic performances in both of his previous games, his ninth-inning home run against the Arizona Diamondbacks on May 27 tied the game 3–3, the Cardinals eventually won by a score of 4–3. He was home in three straight games from June 22-24, including successive games against the Marlins from June 23-24 as St. Louis won both times. In a 12–2 victory over the Mets on July 18, he tied a career record with five hits.

Heyward's first multi-home run game with the Cardinals in an August 16 match against the Marlins. On September 20, the Cubs made an important defensive play. Addison Russell hit a fly ball that Heyward caught running and threw home to catcher Yadier Molina to knock out Anthony Rizzo by two steps, preserving a 4-3 victory. With the bases loaded and no outs in the eighth inning. Heyward beat Pittsburgh 11-1 in their second game of a doubleheader on September 30, giving the Cardinals their 100th victory of the season and their third straight National League Central division championship. In this game, he also stole both Francisco Cervelli and Michael Morse of hits.

Heyward posted a career-high batting average,.359 on-base percentage, and a.439 slugging percentage at the end of the season. Since his major league debut, he has been leading all major league fielders in DRS, and in the previous three seasons, second only to former Braves teammate Andrelton Simmons. Among all outfielders since 2010, Heyward's 96.2 accumulated ultimate zone rating (UZR) led to all major league outfielders to second-place Alex Gordon's 67.3 UZR. Heyward received his third Fielding Bible Award and third Gold Glove Award after becoming a free agent for the first time in his career.

Heyward agreed to an eight-year, $184 million deal with the Cubs on December 15, 2015. On all of the Cubs' road trips during the 2016 season, one of his first acts after signing his deal was to pay for hotel suites large enough to accommodate teammate David Ross, his wife, and their three young children. Ross, who is expected to retire after the 2016 season, was Heyward's teammate during his first three seasons in Atlanta, and Heyward regarded him as a key mentor in his early MLB career. Heyward said in an interview with the Bleacher Report website that he wrote about.

Heyward struggled with the Cubs in his first season in 2016, batting only.230 with 7 home runs and 49 RBIs, while leading the majors in percentage of soft-hit batted batted balls (27.1%), but he's not expected to win his fourth Gold Glove award of the season.

Heyward took second on a bunt force out and moved to second on an errant throw in Game 4 of the 2016 National League Division Series against the San Francisco Giants, with the Cubs leading by a 2–1 series lead. He earned the Cubs the National League Championship Series for the first time after scoring on a Javier Baez single.

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 on October 25, 2016. During a 17-minute rain delay near the end of Game 7 of the 2016 World Series, Heyward was credited with bringing an exciting players-only match. The Cubs won the game 8–7 after ten innings, giving them their first World Series championship in 108 years. Heyward was the first player in Major League Baseball to win three straight Gold Glove Awards with three different franchises (Braves, Cardinals, and Cubs) on November 9, 1989.

Heyward was on the 10-day disabled list on May 8, 2017, after suffering a sprained finger while playing against the Yankees three days before. Heyward sustained a left-hand laceration while playing a foul ball in Pittsburgh in late June and was unable to participate in the next series of games. Heyward had a batting average of.258, a.315 OBP, and.399 SLG in 55 of the first 67 games of the 2017 season. He was third on the team with 29 RBIs and third with 84 total bases. He was put on the disabled list a month later due to a hand injury.

During the 2017 season, Heyward used the term "J-Hey" to describe the Players Weekend.

Heyward was put on the disabled list due to concussion complications after attempting to catch a Dexter Fowler 14th inning home run on May 8, 2018. Jason Heyward scored a walk-off grand slam home run with two outs in the bottom of the 9th to beat the Philadelphia Phillies 7–5. Heyward's year-long work with the Cubs showed continued improvement over his previous work. He had a.285 batting average, with 78 hits in 274 plate appearances, including 6 home runs and 41 RBIs, a.344 OBP, and a.431 SLG.

Heyward had a good start to the season. On April 6, he hit two home runs and stole two bases against the Milwaukee Brewers, becoming only the 18th player — and first Cub — to have a multi-homer, multi-steal game since 1901. It was also his first multi-homer game as a Cub. In a 7-6 victory over the Los Angeles Dodgers, he hit a dramatic three-run home run late in the game to regain the lead. Heyward defeated the Miami Marlins on May 8, giving the Cubs a 3–2 victory. Heyward's third walk-off hit as a Cub (second home run), with the help of a 1-for-20 slump.

Heyward batted.265/.456 in 50 games in the pandemic season, with six home runs and 22 RBIs. His.848 OPS was his best since his rookie season in 2010, and he had a superb 1.000 fielding percentage in right field.

Heyward slashed.214/.347 in 104 games in 2021 with 8 home runs and 30 RBIs.

Heyward was placed on the hospitalized list with a left quadriceps strain on May 8, 2022. In late June, he returned to the Illinois. As Heyward remained on the injured list through August, Cubs general manager Jed Hoyer said the team would release Heyward at the end of the season.

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