After signing with the Minnesota Twins of Major League Baseball in 2015, Whitefield was assigned to the Gulf Coast Twins of the Rookie-levelGulf Coast League. He played in only seven games for the Twins due to visa issues.[3] After the season, he played for the Brisbane Bandits of the Australian Baseball League (ABL) for 2015–16 ABL season. 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. After the season, he played for the Brisbane Bandits of the ABL for 2016–17 ABL season and winning three consecutive championships with the club and the league MVP award.
After the 2019 season, he joined to the Adelaide Bite of the ABL for the 2019–20 ABL season. On 29 June 2020, Whitefield made the Twins 60-man summer camp roster in 2020.[7] He made the Twins Opening Day roster in 2020.[8][9] On 25 July 2020, he made his MLB debut in the ninth inning against the Chicago White Sox as a pinch runner for Eddie Rosario.[10][11] On August 10, Whitefield was outrighted off of the 40-man roster. 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. On November 7, 2021, he elected free agency.[12]
Los Angeles Angels
On 10 November 2021, Whitefield signed a minor league contract with the Los Angeles Angels organization.[13] On 8 May 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.[14] Whitefield was designated for assignment on 14 May 2022. He cleared waivers on 18 May, and was outrighted to Double-A Rocket City Trash Pandas. On 14 October, Whitefield re–signed with the Angels organization on a minor league contract.[15]
Whitefield began the 2023 season back with Double–A Rocket City. In 37 games, he hit just .191/.280/.324 with 3 home runs, 13 RBI, and 12 stolen bases.[16] On 19 June 2023, Whitefield was released by the Angels organization.[17]
On August 20, 2023, Whitefield was traded to the Sioux Falls Canaries in exchange for cash and future considerations.[19] On January 19, 2024, Whitefield re-signed with the Canaries.[20]