Caleb Durbin played at Cooperstown Dreams Park with the Lake Forest Scouts (IL) in 2008, Tournament 6 and with the Chicago North Stars (IL) in 2012, Tournament 10. During his second trip, Caleb helped his team to a 5-1 pool play record for the 11th seed, reaching the Sweet 16 of the single-elimination tournament.

Caleb graduated from Lake Forest High School (Lake Forest, IL). A member of National Honor Society, an Illinois State Scholar, and an AP Scholar, he was a three-year letter winner in baseball, four-year in wrestling and one-year in football. Caleb finished his high school career on the diamond as a record holder in hits (121), stolen bases (72), triples (12) and runs (111). He also holds five high school wrestling records. Additional baseball accolades included two-time All-Conference, two-time All-Area, two-time MVP, High School Male Athlete of the Year, Matt Coutu memorial award, and Bill Rawson memorial award.

As a double major in Economics and Finance, Caleb attended and played baseball at Washington University (St. Louis, MO). An infielder, he finished his freshman campaign Region Rookie of the Year, All-Central Region Second Team, UAA Rookie of the Year, and All-UAA First Team. His sophomore year he was named All-UAA and his junior season he was World Series All-Tournament Team, ABCA/Rawlings Second Team All-Central Region, and All-UAA.

Caleb was selected by the Atlanta Braves in the 2021 Major League Baseball draft. After one season, he was traded to the New York Yankees. On December 13, 2024, Caleb was traded to the Milwaukee Brewers and made his Major League debut on April 18, 2025. He helped the Brewers clinch the 2025 National League Central division.

After the 2025 season, Caleb was traded to the Boston Red Sox.