He made his mark in Cleveland, coaching the Cavaliers from 2005 to 2010 and returning briefly in 2013–14. During his first stint, he led the team to its first NBA Finals appearance in 2007 and won Coach of the Year in 2009 after a 66-win season. The Cavs made the playoffs every full season under his watch, often advancing past the first round.

Brown has had a relatively unusual head coaching career. Rather than starting out with a young team and growing slowly, he was thrown into the fire as the head coach of the Cleveland Cavaliers right as LeBron James began to grow into a superstar.