Following his playing career, Haywood became a college basketball announcer for CBS Sports and a co-host/analyst on SiriusXM NBA Radio.

That season, the Tar Heels advanced to the National Semifinals of the 1998 NCAA Men's Division I Basketball Tournament.

Haywood moved into the starting lineup during his sophomore season, and the Tar Heels earned a #3 seed in the 1999 NCAA tournament, but were eliminated in the first round.

After playing as the Wizards' starting center for the bulk of six years, Haywood began putting up career numbers in the 2007–08 season.

On February 13, 2010, Haywood was traded to the Dallas Mavericks along with Caron Butler and DeShawn Stevenson for Josh Howard, Drew Gooden, James Singleton, and Quinton Ross.

On July 12, 2014, Haywood was traded, along with the drafts right to Dwight Powell, to the Cleveland Cavaliers in exchange for Scotty Hopson and cash considerations.

On July 27, 2015, Haywood was traded, along with Mike Miller and two future second-round draft picks, to the Portland Trail Blazers in exchange for cash considerations.