1990–1993: First championship three-peat

In the 1990–91 season, the Bulls recorded a then-franchise record 61 wins, and romped through the playoffs, where they swept the Knicks in the first round, defeated the Philadelphia 76ers in the semifinals, and then swept the defending champion Pistons in the Conference Finals, then winning the NBA Finals in five games over the Magic Johnson-led Los Angeles Lakers.

The Bulls won their second straight title in 1992 after racking up another franchise record for wins with 67. They swept the Miami Heat in the first round, defeated the Knicks in seven games in the second round, then the Cleveland Cavaliers in six games in the third round, advancing to the Finals for the second year in a row where they defeated the Clyde Drexler-led Portland Trail Blazers in six games.

In 1993, the Bulls won their third consecutive championship by defeating the Atlanta Hawks, Cleveland Cavaliers and New York Knicks in the first three rounds of the playoffs and then defeating regular season MVP Charles Barkley and the Phoenix Suns in the Finals, with Paxson's three-pointer with 3.9 seconds left giving them a 99–98 victory in Game 6 in Phoenix.

1998–2004: Post-dynasty struggles

The summer of 1998 brought an abrupt end to the championship era.^[23] Krause felt that the Bulls were on the verge of being too old and unable to compete. He decided that the team's only choices were to rebuild or endure a slow decline. His plan was to trade away the aging talent and acquire high draft picks while clearing salary cap space to make a run at several promising free agents in two years' time. After having been vetoed in a previous attempt by owner Jerry Reinsdorf, Krause traded Scottie Pippen for Roy Rogers (who was released in February 1999) and a conditional second-round draft pick from the Houston Rockets. He also decided not to re-sign Dennis Rodman, and traded Luc Longley and Steve Kerr for other draft picks. He hired a new coach, Tim Floyd, who had run a successful program at Iowa State University. Upon Phil Jackson's departure, Michael Jordan made his second retirement official. With a new starting lineup of point guard Randy Brown, shooting guard Ron Harper, newcomer Brent Barry at small forward, power forward Toni Kukoč, and center Bill Wennington, the team began the lockout-shortened 1998–99 season. Kukoč led the team in scoring, rebounding, and assists, but the team won only 13 of 50 games. The lowest point of the season came on April 10 in a game against the Miami Heat. In that game, the Bulls scored 49 points to set an NBA record for the fewest points in a game in the shot-clock era.

The previous year's dismal finish came with one highlight: the team won the draft lottery and the rights to power forward Elton Brand. Since the team lost Harper, Wennington and Barry in the off-season, Brand and fellow rookie Ron Artest led the team throughout the year, especially after Kukoč missed most of the season due to injury and was then dealt for a draft pick at the trading deadline. Brand recorded the first 20–10 average for the Bulls since the days of Artis Gilmore. He led all rookies in scoring, rebounds, blocks, field goal percentage and minutes, while Artest led all rookies in steals and finished second on the team in scoring. For his efforts Brand was named 1999–2000 co-Rookie of the Year with Houston's Steve Francis, and to the all-rookie first team, while Artest was named to the all-rookie second team. However, the team established a franchise low at 17–65, second-worst in the league.

After a summer in which the Bulls witnessed most major and minor free agents Tim Duncan, Grant Hill, Tracy McGrady, Eddie Jones and even Tim Thomas choose to stay with their teams (or go elsewhere) rather than sign with them, Krause signed free agent center Brad Miller and shooting guard Ron Mercer, and drafted power forward Marcus Fizer and traded draft pick Chris Mihm to Cleveland for the rights of guard Jamal Crawford. Brand again led the team in scoring and rebounds with another 20–10 season, but the new acquisitions failed to make a major impact, and they finished with the worst record in team history and the league's worst for the season at 15–67.

Krause shocked Bulls fans on draft day in 2001 when he traded franchise player Brand to the Los Angeles Clippers for the second pick in the draft, Tyson Chandler. He also selected Eddy Curry with the fourth pick. Since both Chandler and Curry came straight out of high school, neither was expected to make much of a contribution for several years, but they were seen as potential franchise players. The team floundered without veteran leadership. At mid-season, the Bulls traded their top three scorers—Mercer, Artest, and Miller along with Kevin Ollie—to the Indiana Pacers for veteran guard Jalen Rose, Travis Best and Norman Richardson. There was also a change in coaching, with Floyd being dismissed in favor of assistant coach and former Bulls co-captain Bill Cartwright, following a series of arguments with players and management. The Bulls improved from 15 to 21 wins, although they were still tied for last in the league.

For the 2002–03 season, the Bulls came to play with much optimism. They picked up college phenom Jay Williams with the second pick in the draft. Williams teamed with Jalen Rose, Crawford, Fizer, newcomer Donyell Marshall, Curry, Chandler, and guard Trenton Hassell to form a young and exciting nucleus which improved to 30–52 in Bill Cartwright's first full season as head coach. Curry led the league in field goal percentage, becoming the first Bull since Jordan to lead the league in a major statistical category.

During the summer of 2003, long-time general manager Jerry Krause retired, and former player and color commentator John Paxson was tapped as his successor. Jay Williams, coming off a promising rookie campaign, was seriously injured in a motorcycle accident. His contract was bought out by the Bulls in February 2004, and he never returned to the league. Paxson selected point guard Kirk Hinrich with the seventh pick in the draft, and signed veteran free agent and former franchise player Scottie Pippen. With Pippen playing, Cartwright at the sidelines, and Paxson in the front office, the Bulls hoped that some of the championship magic from before would return.

However, the 2003–04 season was a resounding disappointment. Eddy Curry regressed, leading to questions about his conditioning and commitment. Tyson Chandler was plagued by a chronic back injury, missing more than thirty games. Pippen's ability to influence games was impaired by knee problems, and he openly contemplated retirement. Jamal Crawford remained inconsistent. Bill Cartwright was fired as head coach in December and replaced with former Phoenix coach Scott Skiles. A trade with the Toronto Raptors brought Antonio Davis and Jerome Williams in exchange for Rose and Marshall in what was seen as a major shift in team strategy from winning with athleticism to winning with hard work and defense. After struggling throughout the season, the Bulls finished with 23 wins and 59 losses, the second-worst record in the league. Fizer was not re-signed, and Crawford was re-signed and traded to the Knicks for expiring contracts. Hinrich provided the lone bright spot, becoming a fan favorite for his gritty determination and tenacious defense. He won a place on the All-Rookie first team.

2004–2007: Resurgence

Luol Deng made his first All-Star appearance with the team in 2012 and his second in 2013.

During the 2004 off-season, Paxson traded a 2005 draft pick to the Phoenix Suns in return for an additional pick in the 2004 NBA draft. He used the picks to select Connecticut guard Ben Gordon and Duke small forward Luol Deng in the first round, and Duke point guard Chris Duhon in the second. Paxson also signed free agent small forward Andrés Nocioni, who had recently won an Olympic gold medal as a member of the Argentina national basketball team. After losing the first nine games of the season, the Bulls began to show signs of improvement behind their improved team defense and clutch fourth-quarter play from Gordon. The Bulls, who were 0–9 to start the season, finished the regular season 47–35, with the third-best record in the Eastern Conference and advanced to the NBA playoffs for the first time since Jordan's departure. In the first round, the fourth-seeded Bulls played the Washington Wizards. Despite an injury to Deng and a heart issue with Curry, the Bulls opened the series with two wins at home, but lost the next four games and the series. After the season, Ben Gordon became the first rookie to win the NBA Sixth Man Award and the first Bull since Kukoč in 1996 to win the award.

During the 2005 off-season, the Bulls re-signed free agent Tyson Chandler. However, Curry showed possible symptoms of a heart disease resulting of a heart murmur during checkups, and Paxson would not clear him to play without extensive DNA testing. Ultimately, Curry refused to participate in the tests, and he was traded along with Antonio Davis to the New York Knicks for Michael Sweetney, Tim Thomas, and what became the second pick of the 2006 NBA draft—as well as the right to swap picks with New York in the 2007 NBA draft.

Without a significant post presence, the Bulls struggled for most of the 2005–06 season. However, a late season 12–2 surge allowed them to finish 41–41 and qualify for the 2006 playoffs as the seventh seed. There, the Bulls faced the Miami Heat. After two close losses in Miami, the Bulls broke through with a win in Game 3, and another win in Game 4. However, the Heat took the next two games to win the series and went on to win that year's championship. The Bulls' several young players nevertheless earned additional postseason experience, and Nocioni turned in a remarkable series of performances that far exceeded his season averages.

In the 2006 NBA Draft, the Bulls were awarded forward-center LaMarcus Aldridge and immediately traded him to the Portland Trail Blazers for forward Tyrus Thomas and forward Viktor Khryapa. In a second draft-day trade, the Bulls selected Rodney Carney and traded him to the Philadelphia 76ers for guard Thabo Sefolosha. Later that summer, four-time Defensive Player of the Year Ben Wallace signed with the Bulls for a reported four-year, $60 million contract. Following the signing of Wallace, the Bulls traded Tyson Chandler, the last remaining player of the Krause era, to the (then) New Orleans/Oklahoma City Hornets for veteran power forward P.J. Brown and J. R. Smith and salary cap space that was used to sign former Chicago co-captain Adrian Griffin.

In 2006–07, the Bulls overcame a 3–9 season start to finish 49–33, the third-best record in the Eastern Conference. In the first round, the Bulls again faced Miami, the defending NBA champions. The Bulls narrowly won Game 1 at home, then followed it with a victory in Game 2. In Miami, the Bulls rallied from a 12-point second-half deficit to win Game 3 and then posted another comeback win in Game 4. The Bulls' four-game sweep of the defending champions stunned many NBA observers. It was Chicago's first playoff series victory since 1998, Jordan's last season with the team.

The Bulls then advanced to face the Detroit Pistons, marking the first time the Central Division rivals had met in the playoffs since 1991. The Pistons won the first three games including a big comeback in Game 3. No NBA team had ever come back from a 0–3 deficit to win the series, but the Bulls avoided a sweep by winning Game 4 by 10 points. The Bulls then easily won Game 5 in Detroit, and had a chance to make NBA history. But they lost at home in game 6 by 10, and the Pistons won the series 4–2 on May 17.

2007–2008: Missing the playoffs

Joakim Noah was drafted by the Bulls in 2007. He was named an All Star for the first time in 2013 and for the second time in 2014.

During the off season, the Bulls signed forward Joe Smith and guard Adrian Griffin, and drafted center Joakim Noah. However, distractions began when Luol Deng and Ben Gordon turned down contract extensions, never citing reasons. Then rumors surfaced that the Bulls were pursuing stars like Kevin Garnett, Pau Gasol, and most notably, Kobe Bryant. None of these deals happened, and general manager John Paxson denied a deal was ever imminent.

The Bulls started the 2007–08 season by losing 10 of their first 12 games and on December 24, 2007, after a 9–16 start, the Bulls fired head coach Scott Skiles. Jim Boylan was named the interim head coach on December 27, 2007.

On February 21, 2008, Ben Wallace, Joe Smith, Adrian Griffin and the Bulls' 2009 second-round draft pick were exchanged for Drew Gooden, Cedric Simmons, Larry Hughes and Shannon Brown in a three-team trade deal involving the Cleveland Cavaliers and the Seattle SuperSonics.^[24] Boylan was not retained on April 17 at the conclusion of the 2007–08 season after compiling a 24–32 record with the Bulls. The Bulls ended the 2007–08 campaign with a 33–49 record, a complete reversal of last year's record.

After Jim Boylan's interim tenure expired, the Bulls began 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 did not want to ruin his friendship with Jerry Reinsdorf.

On June 10, 2008, the Bulls general manager John Paxson hired Vinny Del Negro, with no coaching experience, to coach the young Bulls. On July 3, 2008, the Chicago Tribune reported that Del Harris agreed to become an assistant coach for the Bulls along with former Charlotte Bobcats head coach Bernie Bickerstaff and longtime NBA assistant coach Bob Ociepka. Along with Bickerstaff and Ociepka, Harris helped establish a veteran presence on the coaching staff and helped rookie head coach Del Negro.

2008–2010: Appearance of Derrick Rose

With a slim 1.7 percent chance of winning the rights to draft first overall, the Bulls won the 2008 NBA draft lottery and selected first overall.^[25] 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, and second-lowest ever. On June 26, 2008, the Bulls drafted Chicago native Derrick Rose from the University of Memphis as the number 1 draft pick. At pick number 39 they selected Sonny Weems. The Bulls later traded Weems to the Denver Nuggets for Denver's 2009 regular second-round draft pick. The Bulls then acquired Ömer Aşık from the Portland Trail Blazers (selected with the 36th pick) for Denver's 2009 second-round draft pick, New York's 2009 second-round draft pick, and the Bulls' 2010 regular second-round draft pick. The Bulls re-signed Luol Deng to a six-year $71 million contract on July 30, 2008. He was later plagued with an injury keeping him from action for most of the 2008–09 season. Ben Gordon signed a one-year contract on October 2, 2008.

Derrick Rose was drafted first overall by the Bulls in 2008. He was the 2010–11 NBA MVP.

On February 18, 2009, the Bulls made their first of several trades, sending Andrés Nocioni, Drew Gooden, Cedric Simmons, and Michael Ruffin to the Sacramento Kings for Brad Miller and John Salmons.^[26] Then on February 19, 2009, the NBA trade deadline, the Bulls traded Larry Hughes to the New York Knicks for Tim Thomas, Jerome James, and Anthony Roberson.^[27] Later that day the Bulls made the third trade in a span of less than 24 hours by sending swingman Thabo Sefolosha to the Oklahoma City Thunder for a 2009 first-round pick.^[28] The trades brought a late season push for the Bulls, which finally clinched a playoff berth on April 10, 2009, their fourth in the last five years. They finished the season with a 41–41 record. Their record was good enough to secure a No. 7 seed in the 2009 NBA playoffs, playing a tough series against the Boston Celtics. In Game 1, Derrick Rose scored 36 points, along with 11 assists, tying Kareem Abdul-Jabbar's record for most points scored by a rookie in a playoff debut. After breaking the record for most overtimes played in an NBA Playoffs Series, the Boston Celtics managed to overcome the Bulls after 7 games and 7 overtime periods played.^[29]

The Bulls had two first-round picks in the 2009 NBA draft and decided to take Wake Forest stand out forward James Johnson and athletic USC forward Taj Gibson.^[30] In the 2009 NBA off-season the Bulls lost their leading scorer, Ben Gordon, when he signed with their divisional rival, the Detroit Pistons.

On February 18, 2010, John Salmons was traded to the Milwaukee Bucks for Joe Alexander and Hakim Warrick. Meanwhile, Tyrus Thomas was traded to the Charlotte Bobcats for Acie Law, Flip Murray and a future protected first-round pick. On April 14, 2010, the Bulls clinched the playoffs with the number 8 seed. Unlike the previous year, however, the Bulls' playoff run was shorter and less dramatic as they were eliminated by the Cleveland Cavaliers in five games. On May 4, 2010, the Bulls officially fired head coach Vinny Del Negro.^[31]

2010–2011: Arrival of Tom Thibodeau

Tom Thibodeau coached the Bulls to 62 wins in his first season.

In early June 2010, Boston Celtics assistant Tom Thibodeau accepted a three-year contract to fill the Bulls' head coaching vacancy.^[32] He was officially introduced on June 23.^[33] On July 7, it was revealed that Carlos Boozer of the Utah Jazz had verbally agreed to an $80 million, five-year contract. Afterwards, the Bulls traded veteran point guard Kirk Hinrich to the Washington Wizards to create more cap space. The Bulls also signed former 76er and Jazz sharpshooter Kyle Korver to a three-year, $15 million contract. The same day that the Bulls signed Kyle Korver, they signed Turkish All-Star Ömer Aşık. After being matched by the Orlando Magic for J. J. Redick, they signed their third free agent from the Jazz in the off-season in shooting guard Ronnie Brewer, traded for former Warrior point guard C.J. Watson, and signed former Bucks power forward Kurt Thomas as well as former Spurs player Keith Bogans and former Celtic Brian Scalabrine.

Rose earned the 2011 NBA MVP Award, thereby becoming the youngest player in NBA history to win it. He became the first Bulls player since Michael Jordan to win the award. As a team, Chicago finished the regular season with a league-best 62–20 record and clinched the first seed in the Eastern Conference for the first time since 1998. The Bulls defeated the Indiana Pacers and the Atlanta Hawks in five and six games, respectively, thereby reaching the Eastern Conference finals for the first time since 1998, and faced the Miami Heat. After winning the first game of the series, they lost the next four games, ending their season.

2011–2014: Injury-plagued seasons for Derrick Rose

During the off-season, the Bulls drafted Jimmy Butler 30th overall in the 2011 NBA draft. After the NBA lockout ended, the Bulls lost Kurt Thomas to free agency, and released Keith Bogans. The Bulls signed veteran shooting guard Richard "Rip" Hamilton to a three-year deal, after he was waived by the Detroit Pistons. The Bulls also gave MVP Derrick Rose a 5-year contract extension worth $94.8 million.

Derrick Rose was voted as an NBA All-Star starter for the second consecutive year, and was the third leading voted player overall behind Dwight Howard and Kobe Bryant. Luol Deng was also selected as a reserve for the Eastern Conference. This was the first time that the Bulls had two all-stars since 1997, when Michael Jordan and Scottie Pippen were the duo. Derrick Rose was injured for most of the 2011–12 season; however, the team was still able to finish with a 50–16 record and clinched the first seed in the Eastern Conference for the second straight year and the best overall record in the NBA (tied with the San Antonio Spurs). Rose suffered a new injury when he tore his ACL during the fourth quarter of the first playoff game on April 28, 2012, against the Philadelphia 76ers and missed the rest of the series. Head coach Tom Thibodeau was criticized for keeping Rose in the game even though the Bulls were essentially minutes away from their victory over the 76ers. The Bulls lost the next three games, and also lost Noah to a foot injury after he severely rolled his ankle stepping on Andre Iguodala's foot in Game 3; he briefly returned for part of the fourth quarter of that game, but missed the following games in the series. After winning Game 5 at home, the Bulls were eliminated by the 76ers in Game 6 in Philadelphia, becoming the fifth team in NBA history to be eliminated as a first seed by an eighth seed. In Game 6, Andre Iguodala sank two free throws with 2.2 seconds left to put the 76ers up 79–78 after getting fouled by Ömer Aşık, who had missed two free throws five seconds earlier. At the end of the season, Boozer and Aşık were the only members on the Bulls' roster to have played in every game, with Korver and Brewer missing one game apiece. In the off-season, the Bulls gave up Lucas to the Toronto Raptors, Brewer to the New York Knicks, Korver to the Atlanta Hawks, Watson to the Brooklyn Nets and Aşık to the Houston Rockets, but brought back Kirk Hinrich. In addition, they added Marco Belinelli, Vladimir Radmanovic, Nazr Mohammed and Nate Robinson to the roster via free agency.

Rose missed the entire 2012–13 season, but despite his absence, the Bulls finished 45–37, second in the Central Division (behind the Indiana Pacers) and fifth in their conference. They defeated the Brooklyn Nets 4–3 (after leading 3–1) in the first round of the playoffs and lost to the Miami Heat 4–1 in the next round.

During the season, the Bulls snapped both Miami's 27-game winning streak and the New York Knicks' 13-game winning streak, becoming the second team in NBA history to snap two winning streaks of 13 games or more in a season.

Just 10 games into the 2013–14 season, Derrick Rose would tear his medial meniscus on a non-contact play. He declared he would miss the remainder of the season. On January 7, 2014, veteran forward Luol Deng was traded to the Cleveland Cavaliers for center Andrew Bynum and a set of picks. Bynum was immediately waived after the trade went through. The Bulls would finish second in the Central Division with 48 wins, and earned home-court advantage in the first round. Joakim Noah finished the season fourth in MVP voting, made All-NBA first team, and was awarded Defensive Player of the Year award. However, due to lack of a strong offensive weapon, they failed to win a single home game en route to losing to the Washington Wizards in five games.

In the 2014 NBA draft, the Bulls traded their 16th and 19th picks for Doug McDermott, the former Creighton star and fifth-leading scorer in NCAA history, who was selected with the 11th pick, and in the second round, took Cameron Bairstow with the 49th pick. That off-season, they signed Pau Gasol, re-signed Kirk Hinrich and brought over Eurostar Nikola Mirotić, who was acquired via a draft-day trade in 2011, but could not come over sooner, due to salary cap constraints.

2014–2015: Return of Derrick Rose to health and rise of Jimmy Butler

The second return of Derrick Rose gave the Bulls and their fans optimism for the 2014–15 season. With two-time NBA champion Pau Gasol and a deep bench consisting of Taj Gibson, Nikola Mirotić, Tony Snell, Aaron Brooks, Doug McDermott, Kirk Hinrich, among others, the Bulls were one of the two favorite teams to come out of the Eastern Conference along with the Cleveland Cavaliers. The Bulls started off the season in style with a win over the New York Knicks, and then winning seven of their first ninie games (losses coming to the Cleveland Cavaliers and Boston Celtics). The emergence of Jimmy Butler as a primary scorer for the Bulls was a major surprise and he surged into the forefront of the "Most Improved Player of the Year" award race. Butler's statistical jump was noted by many as one of the greatest in NBA History,^[34] going from scoring just 13 points per game in 2013–14 to scoring 20 points per game in 2014–15. Pau Gasol was considered a huge asset for the Bulls and averaged a double-double throughout the season. Both Butler and Gasol ended up making the Eastern Conference All-Star team. The Bulls' second half of the season was marred by inconsistency and frustration set in with Derrick Rose blasting the team for not being on the same page. Tension between management and Tom Thibodeau continued to be a dark cloud hanging over the organization. The Bulls finished with a 50–32 record and the third seed in the Eastern Conference. They faced the Milwaukee Bucks in the first round, and took advantage of the young and inexperienced Bucks by going up a quick 3–0 in the series. However, inconsistency and not being on the same page yet again plagued the Bulls as the Bucks won the next two games, sending a scare to Chicago. The Bulls bounced back with fury in Game 6 however, beating the Bucks by a playoff record 54 points winning the series 4–2. The next round saw the Bulls facing their arch-rival Cleveland Cavaliers, and their biggest nemesis, LeBron James, who had beaten the Bulls in all three of their previous playoff meetings. The Bulls shocked the Cavs in Game 1 dominating them and never trailing. The Cavs answered back in Game 2 in the same fashion, never trailing the entire game. In a pivotal Game 3 in Chicago, the Bulls and Cavs battled closely all the way through, but the Bulls prevailed on a last-second buzzer-beating 3-pointer by Derrick Rose. In Game 4, the Cavaliers would answer once again, with LeBron James hitting the buzzer-beating shot to win the game. The Bulls lack of consistency and poor offensive showing doomed them once again as the Cavaliers won the next two games handily and closed out the series 4–2. After the series, speculation erupted about Tom Thibodeau's job security due to escalating feud between Thibodeau and Bulls front office managers Gar Forman and John Paxson.

2015–2016: Change in approach

Fred Hoiberg was the 22nd head coach in the franchise's history.

On May 28, 2015, the Bulls fired Tom Thibodeau to seek a "change in approach".^[35] The Bulls named Fred Hoiberg as their head coach on June 2, 2015.^[36] The Bulls had only 1 draft pick in the 2015 NBA draft, and selected center Bobby Portis from the University of Arkansas. Bulls forward Mike Dunleavy Jr. was ruled out for at least the first four months of the season after completing back surgery. With Dunleavy out indefinitely, the Bulls promoted Doug McDermott to the starting lineup in his place at small forward. Before the season started, coach Fred Hoiberg made an incredibly controversial move by putting Nikola Mirotić as his starting power forward to pair with center Pau Gasol, meaning Joakim Noah, a long-time Bulls veteran and a fan-favorite was to come off the bench. Hoiberg told the media that the move was suggested by Noah himself but Noah denied having made any suggestions to Hoiberg, which sparked a distrust between the two before the season even began.

The Bulls started the 2015–16 season off well with an impressive season-opening 97–95 victory against archrivals and defending Eastern Conference Champion Cleveland Cavaliers and jumped to an 8–3 record in the first month. The Bulls went 10–9 and through late November and December. The Bulls came back and won six straight games. However, soon afterwards, they lost 12 of their next 17 games and Butler missed four weeks after injuring his knee. The Bulls were eliminated from playoff contention after a loss to the Miami Heat on April 7, 2016, although finishing the season with a winning record of 42–40. It was the first time in 8 years that the Bulls had missed the playoffs.

2017–2020: Final years of GarPax and rebuilding

On June 22, 2017, Jimmy Butler, along with Chicago's 2017 first-round pick, was traded to the Minnesota Timberwolves for Zach LaVine, Kris Dunn, and Minnesota's 2017 first-round pick, which the Bulls used to select Lauri Markkanen. Additionally, on June 27, the Bulls did not give a qualifying offer to Michael Carter-Williams, allowing him to enter unrestricted free agency. On June 30, Rajon Rondo and Isaiah Canaan were waived by the Bulls. On July 10, 2017, Justin Holiday returned to the Bulls signing a 2-year, $9 million contract. On September 24, 2017, Dwyane Wade and the Bulls reportedly agreed to a buyout of the remaining year on his contract. Adrian Wojnarowski reported that Wade gave back $8 million of his $23.2 million contract as part of the agreement.

On October 17, 2017, a fight broke out in practice between Bobby Portis and Nikola Mirotić, who suffered a concussion and two broken bones in his face.^[43] Portis was suspended eight games for his role in the altercation,^[44] and Mirotić missed 23 games to start the regular season. On February 1, 2018, the Bulls traded Mirotić and a second-round draft pick to the New Orleans Pelicans for a first-round draft pick and Ömer Aşık, Tony Allen, and Jameer Nelson.^[43] Bulls ended up finishing the season with 27–55 record.^[45]

On June 21, 2018, the Bulls selected Wendell Carter Jr. with the seventh overall pick, and with 22nd overall pick via trade with New Orleans Pelicans selected Chandler Hutchison. On July 8, the Bulls matched an offer Zach LaVine received from the Sacramento Kings for a four-year, $78 million deal. On July 14, the team signed Jabari Parker to a two-year, $40 million contract after the Milwaukee Bucks' general manager Jon Horst removed the qualifying offer on the restricted free agent and allowed him to become unrestricted. Part of Parker's agreement gave the Bulls a team option for the second year. On December 3, the Bulls fired head coach Hoiberg after the team started the 2018–19 season 5–19 and promoted his assistant Jim Boylen as head coach. On January 3, 2019, the Bulls traded Justin Holiday to the Memphis Grizzlies in exchange for MarShon Brooks, Wayne Selden Jr. and 2019 and 2020 second-round draft picks. MarShon Brooks and Cameron Payne were waived.^[46] On February 6, the team traded Bobby Portis, Jabari Parker and a 2023 second-round draft pick to the Washington Wizards an exchange for Otto Porter. After a season filled with injuries, coaching change, and trades, the Bulls finished with 22–60 record missing the playoffs for the second straight year.

On June 20, 2019, the Bulls selected Coby White with the seventh overall pick and Daniel Gafford with 38th pick in the second round. During the off-season, the team signed veterans Tomáš Satoranský and Thaddeus Young. In March 2020, the league suspended the season after Rudy Gobert tested positive for COVID-19.^[47] In April 2020, the Bulls fired longtime general manager Gar Forman, reassigned John Paxson to senior advisor role and hired Artūras Karnišovas as executive vice president of basketball operations.^[48] In May 2020, the Bulls hired Marc Eversley as general manager. On June 4, 2020, the Bulls season officially came to an end when the NBA Board of Governors approved a plan to bring 22 teams back to finish the season in the NBA Bubble. The Bulls finished with a 22–43 record. Head coach Jim Boylen was fired on August 14, 2020.^[49]

On September 22, 2020, the Bulls hired Billy Donovan as head coach. Donovan had previously coached the Oklahoma City Thunder.^[50]

On November 18, 2020, the Bulls selected Patrick Williams with the fourth overall pick.^[51]

On March 25, 2021, the Bulls traded Wendell Carter Jr, Otto Porter, along with 2021 and 2023 first-round draft picks to Orlando Magic for Nikola Vučević and Al-Farouq Aminu. The team also traded Chandler Hutchison and Daniel Gafford to the Washington Wizards for Troy Brown Jr. and Moe Wagner.^[52] Wagner was later traded along with Luke Kornet to the Boston Celtics for Daniel Theis and Javonte Green.^[53] The Bulls finished the abbreviated 72-game season with 31–41 record missing the playoffs for the fourth consecutive year.

2021–present: Team transformation

On July 29, 2021, the Bulls selected hometown kid Ayo Dosunmu with 38th pick in the second round. On August 2, 2021, the Bulls sent Tomas Satoransky, Garrett Temple, 2024 second-round pick and cash to New Orleans Pelicans for Lonzo Ball.^[54] On the same day, the Bulls managed to sign free agent and 2020 NBA Champion Alex Caruso after he and the Los Angeles Lakers failed to reach an agreement.^[55] As part of the same preseason rebuild, on August 11, Chicago announced a trade sending Thaddeus Young, Al-Farouq Aminu, a protected first-round pick and second-round pick to the San Antonio Spurs in exchange for four-time All-Star DeMar DeRozan.^[56]

While playing against the Indiana Pacers on New Year's Eve in the fourth quarter, DeRozan hit a buzzer-beating game-winning shot to sink the Pacers 108-106. The next day on New Year's Day, While the Bulls were down 117-119, DeRozan hit another buzzer-beating shot to defeat the Washington Wizards 120-119, becoming the first player in NBA History to hit back-to-back game-winning buzzer-beater shots in two consecutive days. The Bulls would then go on to win 9 games in a row. On January 22, 2022, it was announced that DeRozan would start in that year's All-Star Game.^[57] Eight days later, LaVine was named a reserve in the All-Star Game.^[58]

The Bulls finished sixth in the Eastern Conference, narrowly evading the play-ins.^[59] The Bulls played the defending NBA Champion Milwaukee Bucks in the first round where they would lose in 5 games. ^[60] The Bulls star trio Lavine-DeRozan-Vucevic all struggled in this series .^[61][62] On June 23, 2022, Bulls selected Dalen Terry with the 18 pick. On July 7, the Bulls re-signed Zach Lavine to a five-year $215.2 million dollar contract, making this largest contract signed in Bulls history.

On February 21, 2023, the Bulls signed Patrick Beverley for the rest of the season. After the signing, Billy Donovan stated, "You hope that a guy like him coming in gives a boost to our team. That's what he's always been.”^[63] The addition excited the franchise's fans with a new spark of hope for the play-in tournament. His addition aided the Bulls' win against the understaffed Nets, 131–87 on February 24.^[64] The Bulls finished the 2022–23 season with 40–42 record, placing them 10th in the Eastern Conference, thus earning a spot in the play-in tournament. They went on to defeat ninth-seeded Toronto Raptors in the first game but lost the second game to the eventual Eastern Conference champions, the Miami Heat, thus missing the playoffs.

On June 22, 2023, the Bulls traded couple second-round picks to the Washington Wizards to obtain 35th overall pick in the draft to select Julian Philips. The Bulls re-signed both Vučević and Coby White to three-year contracts while also signing veteran players Jevon Carter and Torrey Craig.

1966–1973 uniforms

The Bulls wear three different uniforms: a white uniform, a red uniform, and a black alternate uniform. The original uniforms were esthetically close to the current design, featuring the iconic diamond surrounding the Bulls logo on the shorts and block lettering. What distinguished the original uniforms were the black drop shadows, red or white side stripes with black borders, and white lettering on the red uniforms. For the 1969–70 season, the red uniforms were tweaked to include the city name.^[81]

1973–1985 uniforms

For the 1973–74 season, the Bulls drastically changed their look, removing the side stripes and drop shadows while moving the front numbers to the left chest. While the white uniforms saw the "Bulls" wordmark go from a vertically arched to radially arched arrangement, the red uniforms saw a more significant makeover, featuring black lettering and a script "Chicago" wordmark. With a few tweaks in the lettering, these uniforms were used until 1985.^[81]

This uniform set was later revived as a throwback uniform during the 2003–04 and 2015–16 seasons.

1985–present uniforms

Starting with the 1985–86 season, the Bulls updated their uniform. Among the more notable changes in the look were centered uniform numbers and a vertically arched "Bulls" wordmark in both the red and white uniforms. Like the previous set, this uniform saw a few tweaks particularly in the treatment of the player's name.^[81]

When Nike became the NBA's uniform provider in 2017, the Bulls kept much of the same look save for the truncated shoulder striping and the addition of the Chicago four stars on the waistline. With Nike and the NBA eliminating designations on home and away uniforms, the Bulls also announced that their red "Icon" uniforms would become their home uniforms, and the white "Association" uniforms would become their away uniforms.^[82] The Bulls would continue to wear red "Icon" uniforms in home games until the 2020–21 season, after which they returned to wearing the white "Association" uniforms in home games starting in the 2021–22 season.^[83]

Alternate black uniforms

In the 1995–96 season, the Bulls added a black uniform to their set. The initial look featured red pinstripes and lacked the classic diamond on the shorts. This set was revived as throwback uniforms in the 2012–13 seasons.^[81]

From the 1997–98 to the 2005–06 seasons, the Bulls wore slightly modified black uniforms without pinstripes. This set, with a few slight changes in the template, also marked the return of the city name in front of the uniform during the 1999–2000 season.

The 2006–07 season saw another change in the Bulls' black alternate uniform, now resembling the red and white uniform with the addition of a red diamond in the shorts. For the 2014–15 season, the uniforms were tweaked a bit to include sleeves and a modernized diamond treatment in black with red and white borders.^[81]

Since the 2017–18 season, the Bulls' black uniforms remained mostly untouched for the aforementioned switch to the new Nike logo that affected the treatment towards the shoulder piping. Nike also dubbed this uniform as the "Statement" uniform in reference to its third jerseys. The Bulls began wearing the Statement uniforms after Thanksgiving and they are currently used in away games against teams that wear their white, gray/silver or cream uniforms.

The 2019–20 season marked the return of pinstripes to the Bulls' "Statement" uniform, albeit in dark gray. In addition, the diamond treatment returned to red, piping was tweaked, and four six-point stars were featured on the beltline. The Bulls wore this "Statement" uniform in select home games and away games against teams wearing white, cream, yellow, red or silver uniforms.^[84][85]

Other uniforms

During the 2005–06 season, the Bulls honored the defunct Chicago Stags by wearing the team's red and blue throwback uniforms. The set featured red tops and blue shorts.

From 2006 to 2017, the Bulls wore a green version of their red uniforms during the week of St. Patrick's Day in March. The only red elements visible were those found on the team logo. For 2015 the Bulls wore sleeved versions of the green uniform that featured white lettering with gold and black trim and the "Chicago" wordmark replacing "Bulls" in front. In 2016 and 2017, they wore the same uniforms minus the sleeves.

Between 2009 and 2017, the Bulls wore a variation of their red uniforms as part of the NBA's "Noche Latina" festivities every March. The only notable change in this uniform was the "Los Bulls" wordmark in front. For 2014, the Bulls briefly retired the look in favor of a black sleeved uniform featuring "Los Bulls" in white with red trim.

During the NBA's "Green Week" celebrations, the Bulls also wore green uniforms, but with a slightly darker shade from their St. Patrick's Day counterparts. They used their black alternate uniforms as its template. They donned the uniforms in a game against the Philadelphia 76ers on April 9, 2009.

The Bulls also wore special edition Christmas uniforms as part of the NBA's Christmas Day games. The one-off Christmas uniforms were as follows:

• 2012: Monochrome red uniforms with lettering in red with black trim.
• 2013: Sleeved red uniforms with Bulls logo rendered in silver.
• 2014: Modified version of red uniform featuring the Bulls logo in front and a contrasting white nameplate of the player's first name.
• 2015: Red uniforms with ornate script letters in cream.
• 2016: Monochrome red uniforms with ornate script letters in black.

From 2015 to 2017, the Bulls wore a gray "Pride" sleeved uniform, featuring the team name and other lettering in red with white trim. The shorts featured a more modernized version of the diamond, along with four six-pointed stars on either side.

In the 2017–18 season, the Bulls wore special "City" uniforms designed by Nike. The uniforms, designed to pay homage to Chicago's flag, are in white and feature the classic "Chicago" script and numbers in red with light blue trim along with four six-pointed stars on each side.

The Bulls' 2018–19 "City" uniform is once again inspired from Chicago's flag, with a black base and a portion of the flag with four red six-point stars and two powder blue stripes in front.

The Bulls' "City" uniform for 2019–20 continued the flag theme, featuring a light blue base and a recolored Bulls logo in front. The predominantly blue uniform was also inspired from the waters of Lake Michigan and the Chicago River.

For the 2020–21 season, the Bulls' "City" uniform featured elements of Chicago's Art Deco architecture and imagery, featuring a dark grey base, gold lettering and red accents.

The Bulls' "City" uniform for the 2021–22 season was a "mixtape" of past uniform designs. The predominantly red uniform featured the following design cues:

• Black and white striping, monochrome Bulls logo and white numbers with black drop shadows (1966–73 uniforms)
• Cursive "Chicago" script, recolored to match the numbers (1973–85 uniforms)
• Black diamonds with red pinstripes (1995–97 alternate uniforms)

The 2022–23 "City" uniform paid homage to Chicago's municipal device "Y" symbol. The predominantly white uniform featured rust red letters and black trim, as well as alternating red and black side stripes.^[86]

The Chicago Stadium served as the inspiration for the Bulls' 2023–24 "City" uniform. The black-based design featured the vertical "Chicago" wordmark taken from the Stadium marquee, along with red numbers on the chest and the "Madhouse on Madison" monicker on the jock tag.

Chicago Bulls Ring of Honor

On January 12, 2024, the Bulls introduced the Ring of Honor, which honors former players and other personnel.^[98]

The inaugural class of Ring of Honor inductees included all personnel (players, coaches, executives, etc.) who have had their number retired or were honored with similar banners in the rafters, as well as a number of other contributors to the team over the years, such as original owner Dick Klein and assistant coach Tex Winter. Plans were made to induct a class every two years for people with at least three seasons with the Bulls and being retired from basketball for at least three years.^[99]