He was a three-time all-state selection at Bloomington High School North, and was at one time a teammate of former NBA player Jared Jeffries.

He had strong family connections to IU; his father Scott was a forward on the school's undefeated 1975–76 NCAA championship team and won the Naismith Award the same year, and his brother Scott Jr. played for the Indiana basketball team that made the NCAA title game in 2002.

As a junior, he was named Most Outstanding Player of the 2005 NCAA tournament after leading North Carolina to its fourth national championship.

He started his professional career strongly by being named MVP of the Rocky Mountain Revue summer league.

On October 5, 2007, May announced that he had decided to have micro fracture surgery on his right knee, consequently missing the entire 2007–08 NBA season.

[12] On December 30, 2008, May was deemed physically unfit to play, making Bobcats coach Larry Brown place him on the inactive list for the foreseeable future.

On April 15, May received a promotion from the Director of Basketball Operations position, moving into one of the three on-the-bench assistant spots for Davis' inaugural UNC staff.