3 worst head coach hires in Kentucky basketball history

Unlike Sutton or Smith, Gillispie walked into a tough situation, but unlike Pitino, he didn’t build it up. Kentucky went from 22-12 in Smith’s final year to 18-13 in the 2007-08 season, its first under Gillispie. The Wildcats snuck into the Tournament as an 11 seed and were beaten in the first round. 

Gillispie’s tenure got off to a bizarre start at Kentucky because he never actually signed his seven-year contract to coach the Wildcats. Gillispie agreed to a memorandum of understanding when he was hired, with the assumption that a deal would get done, but it never did. So, when Gillispie went 22-14, equalling the mark for the most losses in a single season in school history, and missed the tournament, he was fired and Kentucky refused to sign his $6 million buyout. 

More than just his failures on the court, there was a difference in philosophy and culture between Kentucky and Gillispie, who never quite seemed to grasp the magnitude of his job. Kentucky athletic director referenced those differences after firing Gillispie. 

After the firing, Kentucky settled on John Calipari, who went to three-straight Final Fours in his first three years and won the title in 2012.