[1] He then attended the University of Central Oklahoma and Grayson County College before being selected by the New York Yankees in the 13th round of the 2006 Major League Baseball Draft.

On July 26, 2008, McCutchen was traded to the Pittsburgh Pirates with Ross Ohlendorf, Jeff Karstens, and José Tábata from the Yankees in exchange for Xavier Nady and Dámaso Marte.

In his first Major League at-bat, McCutchen hit an RBI single off Cincinnati Reds pitcher Kip Wells.

[16] On June 26, 2014, the Chicago White Sox signed McCutchen to a minor league contract, and assigned him to the Triple-A Charlotte Knights.

[18] He made 32 appearances (22 starts) for the Triple–A El Paso Chihuahuas, logging a 9–8 record and 3.60 ERA with 86 strikeouts across 132+1⁄3 innings pitched.

McCutchen split the 2016 campaign between El Paso and the Double–A San Antonio Missions, accumulating an 11–11 record and 6.23 ERA with 87 strikeouts over 29 games (28 starts).