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Frare was non-tendered by Chicago on December 2, 2019, and became a free agent. On December 3, he re-signed with Chicago on a minor league contract.

On July 29, 2018, the Yankees traded Frare to the White Sox for $1.5 million of international signing bonus pool space. The White Sox assigned him to the Charlotte Knights of the Class AAA International League, and promoted him to the major leagues on September 1.

Frare made his professional debut with the Gulf Coast Yankees, posting a 2-1 record with a 2.74 ERA in 23 innings. He did not pitch in 2013 and 2014 while rehabbing from Tommy John Surgery and a quadriceps tear. He returned from the injury in 2015 to pitch for both the Charleston RiverDogs and Tampa Yankees, pitching to a combined 6-3 record and 2.91 ERA in 55.2 total relief innings pitched. He pitched 2016 with Tampa, going 3-3 with a 0.92 ERA in 32 relief appearances, and played 2017 with Tampa and the Trenton Thunder, compiling a 3-4 record and 4.02 ERA in 62.2 total relief innings pitched between the two clubs. Frare started 2018 with Trenton.

He was drafted by the New York Yankees in the 11th round of the 2012 Major League Baseball Draft, and he signed, forgoing his commitment to play college baseball at the University of Utah.

Caleb Michael Frare (born July 8, 1993) is an American professional baseball pitcher in the Chicago White Sox organization. He has played in Major League Baseball (MLB) for the Chicago White Sox.