He made his MLB debut with the Chicago White Sox in 2014 and has also played for the Oakland Athletics and New York Mets.

Prior to playing professionally, he starred for his basketball and baseball teams at Genoa Area High School and the University of Akron.

In his senior year, Bassitt was named to the All-Suburban Lakes League first team in both sports.

He had a 1.56 earned run average (ERA) with 65 strikeouts in 56 innings pitched for the baseball team in 2007, his senior year.

[1] In 2011, his junior year, Bassitt pitched to a 1.42 ERA and limited opposing batters to a .183 batting average against.

[7] After the season, the White Sox assigned him to the Arizona Fall League (AFL), where he pitched in relief for the Glendale Desert Dogs.

[9] On August 30, 2014, Bassitt made his major league debut in a start against the Detroit Tigers.

After the regular season, the White Sox assigned Bassitt to Glendale of the AFL, where he had a 0.69 ERA in 13 innings, striking out 22 batters while walking only three.

[12] After the 2014 season, the White Sox traded Bassitt, Josh Phegley, Marcus Semien, and Rangel Ravelo to the Oakland Athletics in exchange for Jeff Samardzija and Michael Ynoa.

[17] On August 17, 2021, Bassitt was struck in the face by a line drive and exited on a motorized stretcher.

[22][23] On December 16, 2022, Bassitt signed a three-year, $63 million contract with the Toronto Blue Jays.