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Cowart returned to the Angels on February 23, 2019, when they claimed him off waivers from the Tigers. He split the 2019 minor league season between Mobile and Salt Lake. He hit a combined .276/.331/.433/.764 with 9 home runs and 62 RBI, while going 1-2 with a 10.19 ERA over ​17  ⁄3 innings pitched. On September 18, the Angels selected Cowart's contract. Cowart elected free agency following the 2019 season.

During the 2019-20 offseason, Cowart signed a minor league contract with the New York Yankees.

On December 10, 2018, the Seattle Mariners claimed Cowart off of waivers and announced he would come to spring training as a third baseman and as a pitcher. The Mariners designated him for assignment on January 21, 2019, and he was claimed off waivers by the Detroit Tigers on January 24.

After two poor seasons, the Angels assigned Cowart to Inland Empire to start the 2015 season, where he demonstrated an improvement in plate discipline. In June, due to promotions of C. J. Cron, Efren Navarro, and Kyle Kubitza to the major leagues, the Angels promoted Cowart to the Salt Lake Bees of the Class AAA Pacific Coast League, where he batted .323/.395/.491.

The Angels promoted Cowart to the major leagues on August 18, 2015. He made his major league debut that night. After the 2015 season, Cowart changed his uniform number from 41 to 22. In 2016, he appeared in 31 games for the Angels, hitting .176. The following season, he played in 50 games, hitting .225 with 3 home runs. He began the 2018 season in AAA, being recalled during the season. In 47 games, he hit .134 with 1 home run and 10 RBIs.

Cowart attended Cook High School in Adel, Georgia. In his senior year, Cowart played third base and also pitched. As a pitcher he went 10–1 with a 1.05 earned run average in 73 innings, recording 116 strikeouts and one save. As a batter, he hit .654 with 11 home runs, 59 runs batted in (RBIs) and scored 55 runs. He also recorded a 1.206 slugging percentage, a .721 on-base percentage and was 36/36 in stolen bases. His batting average was the second-highest in state history for a single season.

Cowart played for the Cedar Rapids Kernels of the Class A Midwest League and Inland Empire 66ers of the Class A-Advanced California League in 2012. Between the two levels, he had a .276 batting average and 16 home runs in 135 games. Promoted to the Arkansas Travelers of the Class AA Texas League in 2013, Cowart struggled, batting .221 with six home runs and 124 strikeouts in 132 games. Returning to Arkansas in 2014, Cowart batted .223 with six home runs and 99 strikeouts in 126 games.

He was named the 2010 Gatorade National High School Baseball Player of the Year.

The Los Angeles Angels of Anaheim selected Cowart in the first round, with the 18th overall selection, in the 2010 Major League Baseball draft. Though he committed to play baseball at Florida State University, Cowart signed with the Angels.

Kaleb Bryant Cowart (born June 2, 1992) is an American professional baseball third baseman in the New York Yankees organization. He has played in Major League Baseball (MLB) for the Los Angeles Angels. He won the Gatorade High School Baseball Player of the Year Award in 2010. Cowart was drafted by the Los Angeles Angels in the first round (18th overall) in the 2010 Major League Baseball Draft.