They finished the1998-99 season with a disappointing record resulting them to win the draft lottery and acquired Elton Brand.
It was Brand and fellow rookie Ron Artest who led the team through the season. Brand led all the rookies in scoring, rebounding, blocks, field-goal percentage and minutes, averaging 20-10 point-rebound per game. Brand was named Rookie of the Year but they finished with the league’s second worst of 17-65 record.
They continue to struggle for the next several seasons, finishing 15-67 in one of the seasons. They improved in 2002-03, as they have Jay Williams from the draft, Jalen Rose,Donyell Marshall and Chandler, they finished the season with 30-52 record.
In 2003, they drafted Kirk Hinrich as the seventh pick of the draft and signed former Bulls Scottie Pippen. The 2003-04 season was still a disappointment, as their roster and key players were injured or inconsistent. They acquired Antonio Davis and Jerome Williams in exchange for Rose and Marshall. Though, they still finished with 23 wins and 59 losses.
In the offseason of 2004, the Bulls acquired Ben Gordon, Luol Deng and Chris Duhon from the draft. They also signed Andres Nocioni from the free agency. They showed improvement and determination that resulted to 47-35 record. They were the 4th seed in the playoffs and faced off with their soon rivalry Washington Wizards. They lost to the Wizards in the first round in 6 games.
The next season, they resigned Tyson Chandler and traded Eddy Curry and Davis to the Knicks for Tim Thomas and Michael Sweetney.
They struggled early but still finished the season with 41-41 record as they barely qualified for the postseason. They lost against the Miami Heat who later on won the NBA title. In 2006-07 season, with their new roster arrangement with Tyrus Thomas, Ben Wallace, and Sefolosha.
They also traded Chandler for PJ Brown and JR Smith from the Hornets. They finished the season with an impressive 49-33 record. They were the 3rd seed and faced the defending Champions in the first round who they swept in four games. They lost against the Pistons in the 2nd round.
In the offseason, they signed Joe Smith and Adrian Griffin along with the draft center Joakim Noah. They acquired Gooden, Cedric Simmons, Larry Hughes and Shannon Brown for Ben Walla, Joe Smith, Adrian Griffin and 2nd round pick. They finished with a 33-49 record, unable to qualify for the plaoffs.
In 2008, they drafted Derrick Rose as the no. 1 pick overall. They had many changes in their roster that resulted them to acquire Brad Miller and John Salmons. They finished the season with 41-41 record and moved to the playoffs. Rose made a record having 36 points in his playoff debut but eventually they were eliminated in the first round against the Celtics. Rose was named the Rookie of the Year.
In 2009, they drafted Taj Gibson and James Johnson. They lost Ben Gordon to the Pistons, traded Salmons for Hakeem Warrick and Joe Alexander. They also got Acie Law, Flip Murray and future first round pick in exchange of Tyrus Thomas. They were able to qualify for the playoffs but had an early exit in the first round against the Cleveland Cavaliers.
In the offseason of 2010, the Bulls acquired Carloos Boozer from the one of the greatest free agency in the history. They also signed Kyle Korver to their team. They rose as one of the top teams in the 2010-11 season.