The Tampa Bay Devil Rays selected Callaway in the seventh round of the 1996 Major League Baseball draft. Callaway made his major league debut in 1999 with the Devil Rays. In his debut, he pitched 6 innings for the win and went 2-for-3 with a run batted in. The Devil Rays traded Callaway to the Anaheim Angels for minor leaguer Wilmy Caceres before the 2002 season. He was the Angels fifth starter at the end of the 2002 season when Aaron Sele went down with a shoulder injury. He pitched well down the stretch and earned a World Series ring with the Angels, though he did not appear in any postseason games. He was released by the Angels and then subsequently signed by the Texas Rangers at the end of 2003, and finished his Major League career with them in 2004. After the 2004 season, he played in Asia. From 2005 to 2007, he played for the Hyundai Unicorns in the KBO League where he was a two-time league All-Star. In 2005 and 2006, he combined for a total of 30 wins. After being sidelined by an elbow injury in 2007, Callaway served as the interim Head Coach of Texas A&M International University in 2008. In the 2008–2009 off-season, he signed with the Uni-President 7-Eleven Lions of the Chinese Professional Baseball League, and won his final start to clinch a play-off berth for the team.
Coaching career
In 2008, Callaway signed with the Laredo Broncos of independentUnited League Baseball as a player-pitching coach. It would be his last season as a player. Callaway joined the Cleveland Indians organization in 2010 as the pitching coach for the minor league Lake County Captains, champions of the Midwest League. In 2011, he was the pitching coach for the Carolina League runner-up Kinston Indians. Callaway became the pitching coach for the Cleveland Indians prior to the 2013 season. In the 2016 World Series, the Indians were defeated by the Cubs in 7 games. Indians manager Terry Francona said Callaway was the reason they went to the World Series. The Indians produced a Cy Young Award winner in 2014 in Corey Kluber. In 2017, the Indians won an AL-best 102 games, but were defeated by the New York Yankees in the American League Division Series. The Indians led the major leagues in both ERA and in pitching strikeouts. It was the fourth consecutive season they led the American League in strikeouts. The club led MLB in curveball usage in Callaway's time as pitching coach. Callaway was hired by the Los Angeles Angels to be their pitching coach prior to the 2020 season.
Managerial career
New York Mets
On October 23, 2017, Callaway was named the manager of the New York Mets. He replaced Terry Collins, who retired at the end of the 2017 season. In his first twelve games, he helped set a franchise record for the best start in club history at 11 wins and 1 loss. However, he finished the 2018 season with a disappointing record of 77 wins and 85 losses, failing to reach the postseason. He was ejected from a gamefor the first time in his Major League career on June 12, 2018 for arguing with umpire Stu Scheurwater. Callaway was fined by the Mets after a verbal altercation with a reporter after the Mets' 5-3 loss to the Chicago Cubs on Sunday, June 23, 2019. The Mets finished with an 86-76 record in 2019, unable to secure a playoff spot. The Mets fired Callaway on October 3, 2019.
