The San Diego Padres acquired Trent Grisham via trade after he played in 51 games with Milwaukee.

Grisham took over the Centerfield position for the Padres and quickly established himself as an exceptional fielder despite being a light hitter. In 2020, he won a Gold Glove with an OPS of .808, which was arguably his best season in San Diego even though it was shortened by the COVID-19 pandemic. The following year, he batted .242 with 15 Home Runs, but his Batting Average dropped to .184, which is below the Mendoza Line. However, he still managed to hit 17 Home Runs and win his second Gold Glove. In 2023, he failed again to finish over .200 in BA, but his defensive prowess remained solid.

Following the 2023 season, the Padres traded Grisham to the Yankees.