On January 21, 1999, Billups was dealt to his hometown Denver Nuggets in a three-way deal involving one of Billups's future teams, the Minnesota Timberwolves. Minnesota received Dean Garrett and Bobby Jackson from Denver, Toronto received Željko Rebrača and Micheal Williams from Minnesota and the 5th pick in the 1999 NBA draft from Denver, and Billups, along with Tyson Wheeler, was sent to Denver from Toronto. Three months into his first tenure with the Nuggets, Billups visited a local Denver hospital in order to comfort and inspire Patrick Ireland, a victim of the 1999 Columbine High School Shooting Massacre. A year later, on February 1, 2000, Billups was traded to the Orlando Magic along with Ron Mercer and Johnny Taylor in exchange for Chris Gatling, Tariq Abdul-Wahad, a future first-round pick, and cash.