Yoshida played college baseball for Aoyama Gakuin University and was selected by the Orix Buffaloes in the first round of the 2015 NPB draft.

[2] On December 7, 2022, Yoshida was posted by Orix and made available to all 30 Major League Baseball (MLB) teams, opening a 30-day period to negotiate a contract.

[4] On December 15, Yoshida signed a five-year contract with the Boston Red Sox,[5][6] reportedly worth $90 million.

[7] That ranking was considered "alarmingly low" by Peter Abraham, the Red Sox beat writer for The Boston Globe.

[7] On April 23, 2023, Yoshida hit two home runs in the same inning, including a grand slam, in a game against the Milwaukee Brewers.