Reynolds played college baseball for the Vanderbilt Commodores, and the San Francisco Giants selected him with the 59th pick in the 2016 MLB draft.

The San Francisco Giants selected Reynolds in the second round of the 2016 Major League Baseball draft.

He spent 2017 with the San Jose Giants where he posted a .312 batting average with ten home runs and 63 RBIs in 121 games.

On January 15, 2018, the Giants traded Reynolds, Kyle Crick, and $500,000 of international bonus slot money to the Pittsburgh Pirates in exchange for Andrew McCutchen and cash considerations.

[12] He made his major league debut that afternoon versus the San Francisco Giants and recorded his first career hit, a single, off Derek Holland.

[13] On April 30, he hit his first major league home run off Texas Rangers' reliever Jesse Chavez.

His performance improved significantly the following season: he was one of two Pirates, along with Adam Frazier to play in the 2021 All-Star Game, where he started in center field and batted eighth.

[21] After a slow start to the season, Reynolds finished 2022 hitting .262/.345/.461 with 62 RBIs, and a career high 27 home runs.