For the 2012 season, Watkins played for the Double-A Tennessee Smokies, slashing .281/.383/.422 with new career-highs in home runs (9) and RBI (52).

On August 4, 2013, the Cubs promoted Watkins to the major leagues and made his debut as the starting second baseman against the Los Angeles Dodgers, going 1-for-4.

[5] On February 4, 2015, Watkins suffered a torn Achilles tendon while working out, and missed the entire season as a result.

[8] He split the 2017 season between the Triple-A Toledo Mud Hens and the Double-A Erie SeaWolves, posting a .242/.343/.300 slash line with 2 home runs and 21 RBI in 86 games between the two teams.

On January 7, 2020, Watkins was traded to the Olmecas de Tabasco of the Mexican League in exchange for Humberto Castro.

[11] On April 5, 2021, Watkins was announced as the new hitting coach for the Cleburne Railroaders of the American Association of Professional Baseball.