[11] Gentry did not play in a game in 2020 due to the cancellation of the minor league season because of the COVID-19 pandemic.

Gentry opened the 2022 season with Quad Cities and was promoted to the Double–A Northwest Arkansas Naturals in early June.

[15][16][17] Over 108 games between the two teams, he slashed .326/.422/.542 with 21 home runs, 86 RBI, 22 doubles, and 10 stolen bases.

On August 25, 2024, Gentry was selected to the 40-man roster and promoted to the major leagues for the first time.

[24] He made his debut later that day in an 11–3 Royals loss to the Philadelphia Phillies, coming in to pinch-hit for MJ Melendez in the bottom of the eighth inning.

Facing José Alvarado, Gentry swung at the first pitch and flew out to right fielder Nick Castellanos.