Caleb was born and raised in Miles City. He was selected to play for Bobby Valentine All-American team in 2010 & 2011. He was chosen to play in the Area Code games in 2011. Caleb graduated from Custer County High School in 2012 after playing for the Miles City Outlaws. He was drafted by the New York Yankees in the 11th round of the 2012 Major League Baseball Draft. Caleb signed, forgoing the opportunity to play college baseball at the University of Utah. He was in the NY Yankees minor league system for 7 years. During this time, Caleb was a Double-A All Star with the Trenton Thunder and a runner up for Minor League reliever of the year. While in Triple A with the Yankees, he posted an ERA of 0.62, and was traded to the Chicago White Sox in 2018 for $1.5 M in international bonus pool money. After a month in the White Sox Triple A, he made his Major League Debut against the Boston Red Sox. In 2019, Caleb pitched in the major league for the Chicago White Sox after making the opening day roster in 2019. After an off-field injury in 2019 and COVID, Caleb continued to play baseball in 2021 for the Sioux Falls Canaries in the American Association. Following the 2021 season, Caleb decided to retire to prioritize being a husband to Danielle Frare and a father to Michael and Vanessa. Caleb owns a third party logistics company based in Miles City. This is his first year coaching at the college level.