In 2016, Whitefield returned to the Gulf Coast League and played in 51 games, posting a .298 batting average with two home runs, 17 RBIs and 31 stolen bases.

In 2017, Whitefield played for the Cedar Rapids Kernels of the Single–A Midwest League,[1] where he batted .262 with 11 home runs, 57 RBIs, and 33 stolen bases.

[8][9] On July 25, he made his MLB debut in the ninth inning against the Chicago White Sox as a pinch runner for Eddie Rosario.

Whitefield spent the 2021 season with Double-A Wichita Wind Surge, slashing .257/.327/.353 with 6 home runs and 58 RBI in 111 games.

[13] On May 8, 2022, he was promoted to the Angels' main roster after playing for the Double-A Rocket City Trash Pandas of the Southern League, where he batted .301 with 5 home runs, 17 RBIs, and 13 stolen bases.

[17] On 27 June 2023, Whitefield signed with the Kansas City Monarchs of the American Association of Professional Baseball.

On August 20, 2023, Whitefield was traded to the Sioux Falls Canaries in exchange for cash and future considerations.