He has previously played in Major League Baseball for the Kansas City Royals, Oakland Athletics, and Chicago Cubs.

He played for the Lexington Legends and the Wilmington Blue Rocks in 2014, combining to hit .280/.309/.500/.809 with 22 home runs and 75 RBIs in 118 games.

In 2015, Schwindel played for Wilmington and the Northwest Arkansas Naturals, he combined to hit .252/.281/.383/.664 with seven home runs and 54 RBIs in 123 games.

He split the 2017 season between Arkansas and the Omaha Storm Chasers, combining to hit .329/.349/.541/.890 with 23 home runs and 97 RBIs in 133 games.

[13] Schwindel split the remainder of the season between the Triple-A Toledo Mud Hens, the Double-A Erie SeaWolves, and the High-A Lakeland Flying Tigers.

[18] On June 30, Schwindel hit his first major league home run in his first at-bat with Oakland against Kolby Allard of the Texas Rangers.

Schwindel hit .344 with six home runs, 18 RBI, a .394 on-base with a .635 slugging and a 1.030 OPS in August, and won the National League Rookie of the Month Award.

[22] On September 5, Schwindel hit a go-ahead grand slam that put the Cubs up to stay in an 11–8 win over the Pirates.

[24] In his first full major league season, between Oakland and Chicago, Schwindel batted .326 with 14 home runs and 43 RBI, which despite only playing in 64 games was good enough to earn him two votes in National League Rookie of the Year voting, tying him for sixth place with Tyler Stephenson.