The New York Yankees selected Hensley in the first round, with the 30th overall selection, of the 2012 Major League Baseball draft. Though the Yankees and Hensley agreed on a $1.6 million signing bonus, a physical examination discovered an abnormality in the shoulder of his pitching arm. As a result, the Yankees reduced the offered bonus to $1.2 million; Hensley agreed to the reduced bonus and signed with the Yankees rather than attend Ole Miss. After signing, Hensley made his professional debut in Minor League Baseball with the Gulf Coast Yankees of the Rookie-levelGulf Coast League. He pitched 12 innings for the Gulf Coast Yankees. He suffered an abdominal musclestrain while pitching in the Dominican Republic during the offseason. Though he rehabilitated the injury, he felt pain in his hip during spring training in 2013, which was diagnosed as a hip impingement. He required surgery to repair both hip labrums, and caused him to miss the entire 2013 season. He pitched for the Gulf Coast Yankees and the Staten Island Yankees of the Class A-Short SeasonNew York–Penn League in 2014. Between the two levels, he had a 2.93 ERA in innings pitched across 11 appearances. Hensley began experiencing discomfort in his arm during spring training in 2015. An MRI and arthrogram found a bone calcification inside a torn ulnar collateral ligament of the elbow. He underwent Tommy John surgery and missed the 2015 season. While rehabilitating, the Yankees announced that Hensley would need a second Tommy John surgery in May 2016. He missed the 2015 and 2016 seasons due to injury. At the 2016 Winter Meetings, the Tampa Bay Rays selected Hensley from the Yankees in the minor league phase of the Rule 5 draft. He missed the 2017 season due to injury. The Rays released Hensley, and he signed with the Evansville Otters of the Frontier League, an independent baseball league, in May 2018. In 2019, Hensley pitched for the Utica Unicorns of the United Shore Professional Baseball League.
Personal life
Hensley's father, Mike, played for college baseball for the Oklahoma Sooners and for the St. Louis Cardinals' organization in Minor League Baseball. After Mike's career ended due to an injury, he worked as a pitching coach for Oral Roberts University and Kansas State University. Hensley has a brother, J. R., who also pitches and plays left tackle for the football team. Following the 2014 season, Hensley was assaulted and seriously injured in a town near his home. Anthony Morales, an American football linebacker who played college football for Weber State University, allegedly attacked Hensley, kicking him in the head, when they argued about signing bonuses, and Hensley refused to tell Morales how much he received in his signing bonus. Hensley lost consciousness and suffered a broken jaw. He spent several days at INTEGRIS Southwest Medical Center. Morales was charged with aggravated assault and battery, but later acquitted of the crimes.