A look back at Derrick Rose’s time in Chicago.

By Jeremy Woo
June 22, 2016

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Derrick Rose’s time in Chicago came to a close on Wednesday, as the Bulls stunned the public at large by sending the former MVP to the New York Knicks.

There’s a lot to unpack with this deal, which brought back defensive-minded center Robin Lopez as the main piece for the Bulls. Rose has one year left on his contract. It’s a calculated gamble for both sides. But given Rose’s long history in his native city, dating back to high school stardom through his professional peak and the injuries that followed, it’s the first major ripple in a very young NBA off-season.

For old times’ sake, let’s look back at Rose’s career and where it’s headed.

• Grades: Knicks' trade for Rose all sizzle, no steak

The auspicious start

After the Bulls beat the odds and won the 2008 draft lottery despite a 1.8% chance of landing the top pick, they sparked additional conspiracy theories by taking the hometown kid in Rose, fresh off a Final Four run at Memphis and a former two-time state champion at Simeon Career Academy. They picked him over Kansas State forward Michael Beasley. It was the first real fresh start for the franchise since Michael Jordan retired and the championship-winning Bulls disbanded in 1998.

Story short, he became a star almost immediately. He won Rookie of the Year, helped lead the Bulls to the playoffs, and nearly led them to a first-round upset against the defending champion Boston Celtics. That playoff series would go down as arguably one of the best ever. This mix is 53 minutes long, but seriously, watch all of it.

The youngest MVP ever

Rose was an All-Star in his second season, but the Bulls were bounced by LeBron James and the Cavaliers in five games. He came back the next season with a vengeance and a new head coach in Tom Thibodeau, perhaps the most highly-esteemed assistant in the league alongside Doc Rivers in Boston. Rose, Luol Deng, free-agent addition Carlos Boozer and Joakim Noah formed a strong core. The Bulls were back.

Before the season, Rose delivered a famous speech, asking, “Why can’t I be MVP of the league?”

Spoiler alert: he went and did it. Rose became perhaps he league’s most dominant scoring point guard, averaging 25 points, 7.7 assists, 4.1 rebounds and a steal in leading Chicago to the top of the Eastern Conference at 62–20. At 23 years and two months old, he became the youngest MVP in NBA history.

The Bulls bowed out against the Miami Heat in five games, led by the new big three of James, Dwyane Wade and Chris Bosh. A real rivalry appeared to be brewing. 

Just watch this mixtape. It’s ridiculous. It’s peak Derrick Rose.

The first knee injury

Alright, we’re kind of skimping on a third straight All-Star season here. He opened it by signing a five-year contract extension that would take up 30% of Chicago’s salary cap, the maximum allowed under a stipulation in the 2011 collective bargaining agreement that was later dubbed the “Derrick Rose rule.” This was also the year of the lockout, which officially was ratified and ended Dec. 8. The season began on Christmas.

Chicago made it back to the playoffs, again winning the East regular season at 50–16. And then, in the first game of the postseason, against the Sixers, Rose tore his left ACL. Chicago bowed out in six games in that series and watched as the Heat won their first title.

Rose would miss the entire 2012–13 season and drew media skepticism for waiting his injury out. The recovery was slow-rolled and highly-publicized. Shoe sponsor adidas launched a huge marketing campaign around their signature star. That hype never quite mounted anywhere. Miami won another title, but not without the Bulls scrapping their way to the East semifinals, led by Noah, their emotional center, and Thibodeau’s defensive-minded scheming.

The first return, the second exit 

Rose finally took the floor to open the 2013–14 preseason. He told reporters in October that his vertical had actually increased by five inches. He began getting his legs under him as the season began with mixed effectiveness. In Chicago’s home opener, on Halloween against the Knicks, this happened.

And then he tore his right meniscus. On Nov. 22 against the Portland Trail Blazers, Rose went down again. He had surgery three days later and missed the rest of the season.

Chicago went 48–34 and went out in the first round against the Washington Wizards. D.J. Augustin and Kirk Hinrich were playing point guard. Dire times. Awful ones.

Another comeback, another injury, another comeback

Rose came back again in time to start the 2014–15 season. There was even more discourse as to his health, his long-term ability, his confidence and where the Bulls were headed. Patience had begun to wear somewhat thin with a chunk of the fan base. Rose returned, again, and wasn’t himself — perhaps he never would be — but the Bulls were improving and Jimmy Butler emerged as the viable shooting guard they needed.

On Feb. 24, Rose tore his right meniscus again. It was unbelievable and eminently real at the same time. He would miss just 20 games this time and return in time for the playoffs. His explosion came and went, his jump shot often waned, but he averaged 21.5 points per game in a first-round series win over the Bucks.

The Bulls met LeBron James, back on the Cavaliers, in the semifinals. Long their playoff tormentor, James would hit a game-winner in Game 4 to tie the series 2–1 and eventually galvanize Cleveland toward the Finals. But not without this sliver of hope from Rose, in what may be his lasting highlight as a Bull.

The shot won Game 3. It wasn’t enough, but it was a moment, to be sure.

The eventual outs

Rumors began to swirl entering 2015–16 that Rose and Butler, who’d become a star in his own right, had begun to clash and that their styles of play couldn’t co-exist. Whether or not that was true, the Bulls soldiered on. Tom Thibodeau was fired, his relationship with the front office having worn down both sides over the past few years.

Like clockwork, Rose suffered an orbital bone fracture in the very first practice of the season. He returned wearing a facemask in time for the regular season. It would be Rose’s healthiest campaign since 2011 and his most statistically effective, averaging 16.4 points and shooting 42.7% from the floor, but one full of tumult for Chicago. The Bulls lumbered to a 42–40 record and missed the post-season under new head coach Fred Hoiberg, all the angst from years past catching up to everybody. The Bulls were out of the playoffs for the first time since the pre-Rose era.

And on June 22, 2016, Rose was dealt to the Knicks. GM Gar Forman called it a “retool” in his press conference. He spoke like he intended to keep Butler, and use the newly-acquired center Robin Lopez and point guard Jerian Grant as building blocks. The deal perhaps signaled the exits of two Bulls cornerstones, as Lopez appeared the clear replacement for soon-to-be free agent Joakim Noah.

Rose is a Knick, for better or worse. And needless to say, it’s weird for everybody.

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