Best was a vital backup at point guard on the 1999-2000 Indiana team that went to the 2000 NBA Finals. Best hit the game-winning 3-pointer in the decisive fifth game against the Milwaukee Bucks in the first round of the playoffs. During the 2001-2002 season, he requested a trade and was granted one to the Chicago Bulls. The Bulls traded Ron Artest, Brad Miller, Ron Mercer and Kevin Ollie to the Pacers for Best, Jalen Rose and Norman Richardson, adding a future second-round pick.