He has previously played in Major League Baseball (MLB) for the Atlanta Braves, St. Louis Cardinals, Chicago Cubs, Los Angeles Dodgers, and Houston Astros.Originally the Braves' first-round selection in the 2007 MLB draft from Henry County High School in Georgia, Heyward began his minor league career at age 17.He won both the Fielding Bible and the NL Gold Glove Awards for right fielders in 2012, 2014, 2015, 2016 and 2017, and he received Wilson's MLB Defensive Player of the Year in 2014.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.Heyward hit a game-tying 400 ft (120 m) home run in Game 2 to cap an eight-run comeback, but Lee County prevailed 14–10.[9] 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.[11] Numerous colleges showed interest and recruited Heyward, including UCLA, which offered a full-ride scholarship due in part to the family connection.[23] 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.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.[26] Heyward made his postseason debut on October 7, 2010, in the National League Division Series (NLDS) against the San Francisco Giants.[39] 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.[59] New York Mets pitcher Jon Niese hit Heyward in the face with a pitch on August 21, fracturing his jaw in two places.[63] 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.[74] 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.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.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.[89] 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.[85] 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).[94] 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.[34] 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.[97] 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.[98] 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.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.[113] He made the Dodgers' Opening Day roster,[114] reworked his swing,[115] accepted a platoon role,[116] and enjoyed a resurgent season.[34] 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.[123] During his debut as an Astro, Heyward hit a key two-run double that spearheaded a 6–3 win versus the Kansas City Royals.[124] 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.[126] 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.