He made his minor league debut with the Low–A Tri-City ValleyCats on June 20, 2019, where he saw his first professional hit, a two-out double in the 6th inning, in that initial game.

For the 2022 season, Kessinger remained with Corpus Christi, playing in 121 games and batting .211/.327/.366 with career-highs in home runs (16), RBI (58), and stolen bases (23).

[10] Kessinger began the 2023 season with the Triple-A Sugar Land Space Cowboys, playing in 52 games and hitting .284/.400/.443 with 6 home runs and 32 RBI.

Kessinger joined his grandfather, Don, and uncle, Keith, as the third generation of his family to hit a home run in Major League Baseball.

[14] On January 7, 2025, the Astros traded Kessinger to the Arizona Diamondbacks in exchange for minor league pitcher Matthew Linskey.

His father, Kevin, was drafted by the Cubs, but retired from professional baseball due to injury before playing in the major leagues.