After Jim Boylan's interim tenure expired, the Bulls have been in the process of selecting a new head coach. They were in talks with former Phoenix head coach, Mike D'Antoni, but on May 10, 2008 he signed with the New York Knicks. Other possible options included former Dallas head coach Avery Johnson and former Bulls head coach Doug Collins. Collins resigned from the coaching list on June 4, 2008, reporting that he didn't want to ruin his friendship with Jerry Reinsdorf.

On June 10, 2008 the Chicago Bulls G.M. John Paxson hired Vinny Del Negro, with no coaching experience, to coach the young Bulls. The stage was set for a new era in Bulls history.

With a 1.7% chance of winning the rights to draft number 1 in the 2008 NBA Draft, the Bulls won the NBA Draft Lottery and selected first overall. With this, the Bulls became the team with the lowest % chance of winning to ever win the lottery since it was modified for the 1994 NBA Draft. On June 26, 2008 The Bulls Drafted Derrick Rose As the Number 1 draft Pick and at pick Number 39 they selected Sonny Weems. The Bulls later traded Sonny Weems (selected with the 39th pick) to the Denver Nuggets for Denver's 2009 regular second round Draft pick. The Bulls then acquired Omer Asik from the Portland Trail Blazers (selected with the 36th pick) for Denver's 2009 regular second round Draft pick, New York's 2009 regular second round Draft pick, and the Bulls 2010 regular second round Draft pick.