Callahan attended Dillon High School. He earned the 2012 Gatorade South Carolina Baseball Player of the Year and Region 8-2A Player of the Year in his senior season, after posting a 7–1 win–loss record with a 0.89 earned run average (ERA) and 111 strikeouts in 50 innings pitched to help his team reach the regional championship. In addition, he was an All-State selection in 2011 and 2012. Callahan committed to play college baseball for the South Carolina Gamecocks.\n', '

The Boston Red Sox selected Callahan in the second round (87th overall) of the 2012 MLB Draft and he chose to forego his commitment to South Carolina in favor of a $565,500 signing bonus. He was assigned immediately to the Gulf Coast Red Sox where he was 1-0 with a 5.19 ERA in 8.2 innings pitched. In 2013 he pitched for the Lowell Spinners where he was 5-1 with a 3.92 ERA in 13 games (12 starts), in 2014 he played with the Greenville Drive where he pitched to a 3-13 record with a 6.96 ERA in 25 starts, and in 2015 he returned to Greenville where he was 7-6 with a 4.53 ERA in 31 games (six starts). Callahan spent 2016 with the Salem Red Sox where he posted a 5-3 record and 3.29 ERA in 36 relief appearances, and he began 2017 with the Portland Sea Dogs. He was promoted to the Pawtucket Red Sox in May.\n', '

On July 31, 2017, the New York Mets acquired Callahan, Stephen Nogosek, and Gerson Bautista in exchange for Addison Reed. New York assigned him to the Las Vegas 51s. The Mets promoted Callahan to the major leagues on September 1. In 41 relief appearances between Portland, Pawtucket, and Las Vegas prior to his promotion he was 6-3 with a 2.94 ERA. He made his Major League debut on September 2 against the Houston Astros at Minute Maid Park.\n', '

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