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5 best trades in Chicago Bulls history, ranked

The Chicago Bulls are one of the most decorated franchises in NBA history, dominating the ‘90s by winning a total of six Larry O’ Brien trophies. Those championships wouldn’t have been made possible if not for some key trades they made along the way.

But if you follow the team closely, it’s safe to say that Chicago’s best trades are the ones they actually didn’t make.

It sounds blasphemous to even think about it right now, but the Bulls brass actually once considered trading away Hall of Famers’ and all-time greats’ Michael Jordan and Scottie Pippen at one point.

The Bulls franchise wouldn’t have definitely been relevant if those deals pushed through.

Still, the Windy City franchise definitely struck gold with some of the trades they pulled the trigger on. Let’s rank five of the best Bulls trades in history.

5. Carlos Boozer (2010)

Despite his defensive limitations, Boozer still carved out a solid career – particularly during his four-year stint with the Bulls from 2010 to 2014.

While he was no longer the All-Star forward by the time he left the Utah Jazz, the 6-foot-9 power forward still gave Chicago a dependable scorer on the low block.

Chicago acquired Boozer via a sign-and-trade deal with Utah prior to the 2010-11 season, in exchange for a traded player exception (TPE).

Booz played second fiddle to Derrick Rose on offense, norming 15.5 points, 9.0 rebounds, and 2.0 assists in 280 games played in a Bulls uniform. Unfortunately for Chicago, they couldn’t get past the Eastern Conference Finals during Boozer’s stint.

4. Bill Cartwright (1988)

Cartwright had some big shoes to fill upon joining the Bulls team in 1988 since he was traded from the Knicks in exchange for locker room favorite Charles Oakley.

While he was no longer around during the second half of the Bulls’ three-repeat, the 7-foot-1 center played a major role in the team’s first one from 1991-93.

His relationship with Michael Jordan wasn’t exactly amicable at the time, since MJ often ridiculed him and even called him “Medical Bill” due to his injury history.

Still, even the GOAT himself admitted in “The Last Dance” that Chicago probably wouldn’t have been able to get past their tormentors Detroit Pistons had Cartwright not been around.

Cartwright spent six seasons with the Bulls, contributing 9.2 points, 5.5 rebounds, and 1.5 assists in 397 games.

3. Zach LaVine (2017)

The Bulls wisely wanted to get a bright young talent in exchange for their then disgruntled star Jimmy Butler. While they also managed to snag Kris Dunn and Lauri Markkanen in the deal, no doubt Chicago had their sights set on the two-time Slamdunk Contest Winner.

Aside from his nuclear hops, LaVine brought in an uncanny ability to score from anywhere in the court. This intrigued the Bulls since they were in dire need of a go-to scorer at the time.

The UCLA alum soon proved that he is ready to be his own man after playing behind the shadows of Karl Anthony Towns and Andrew Wiggins in Minnesota. While Butler’s two-way prowess was missed, LaVine gave them another premier talent to build around.

The Bulls were part of the Delete 8 teams not to enter the bubble last month, but LaVine’s amazing individual season gave them some hope for the future. The 6-foot-6 high-flyer led his team in points norming 25.5 in 60 games, to go along with 4.8 rebounds, 4.2 assists, and 1.5 steals.

2. Dennis Rodman (1995)

The Bulls took a major gamble when they traded for “The Worm” prior to the 1995-96 season. Following their disappointing second-round exit in the ’95 playoffs, Chicago knew they had to find a suitable power forward who could replace Horace Grant’s production.

Rodman was a respected defender and legendary rebounder but was considered a wildcard around the league. His testy relationship with Bulls stars Michael Jordan and Scottie Pippen didn’t help either. Still, Chicago believed bringing him was for the best, flipping serviceable back-up big Will Purdue to the San Antonio Spurs for Rodman’s services.

The rest, as we know it, is history. Rodman’s willingness to do the dirty work brought Chicago back to the top of the pecking order, masterfully anchoring head coach Phil Jackson’s defense from 1995-98. It’s no coincidence that the Bulls won it all each year during Rodman’s short but sweet stay.

1. Scottie Pippen (1987)

As much flak as the late former Bulls GM Jerry Krause has gotten since “The Last Dance” aired, there’s no doubt that the man had a great eye for talent. The Bulls gave up quite a lot to move up in the 1987 draft since they were dead set at picking the unheralded player from Arkansas at the time.

The Bulls definitely made the right choice trading for the No.5 pick, which they used to select Scottie Pippen. They shipped their 8th pick at the time, Olden Polynice,  as well as a 1988 second-round pick and a 1989 first-rounder.

Pippen had an up-and-down relationship with the Chicago brass but he made those six NBA titles possible.

It’s quite ironic that Krause moved heaven and earth to trade for Scottie in his rookie year, only to put him on the trading block numerous times throughout his stay in Chicago.