“With the first pick in the 2008 NBA Draft, the Chicago Bulls select… “
Derrick Rose.
One.
A one percent chance for the Chicago Bulls to draft number one in the 2008 NBA Draft.
One player mocked in the first round who was born in Chicago.
One—the number he wore on the back of his jersey for the Bulls.
One player to win the NBA Most Valuable Player award at the age of 22 or younger.
And one—the number that will forever be retired by the Chicago Bulls for Derrick Rose tonight.
The moment Derrick Rose sees his banner for the first time and is joined by his family, Joakim Noah, Taj Gibson, and Kirk Hinrich ? pic.twitter.com/0Mh6VGTbXl
— Chicago Bulls (@chicagobulls) January 23, 2026I started watching the NBA in 2009, when I was just seven years old. And by the time I was 12, I had already cried and begged for a pair of shoes with the flower on them, like the man on the TV—hoping I could jump out of the gym like him. (Spoiler alert: I couldn’t.)
And here I am, almost two decades later, still talking about the legacy he left behind.
Derrick Rose: The Basketball Player
© Mike DiNovo-Imagn ImagesThe seed was sown at Simeon, a powerhouse high school program in Chicago’s Englewood neighborhood that has a long history if state championships, elite prospects and future NBA players.
It was at Simeon where the world began to take notice of Derrick Rose. Back-to-back state championships. Leading Simeon to become the first Illinois team to play at Madison Square Garden. Illinois’ Mr. Basketball. Gatorade Player of the Year. McDonald’s All-American. A top-five prospect in the nation. Countless heroic moments, all while donning the number 25.
A number reserved for the best player on the team, worn in memory of “Benji” Wilson—who was shot in broad daylight during his lunch break, just a few steps from his school.
“Went to the high school and I watched him,” said John Calipari, former head coach of the Memphis Tigers. “And I’m like, I got to have this guy.”
And the first stem came out of the mud.
In his one season at Memphis, Derrick Rose went all the way to the National Championship game—and lost by just seven points, in a season where losses were few and far between. It was Calipari’s first national championship appearance, in a career that is now considered one of the greatest.
Hence, it was no surprise that when the Chicago Bulls landed the number one overall pick, they would draft Rose—something LeBron James and others considered a little too perfect for the storybooks. But I digress.
LeBron been said the lottery is rigged lol pic.twitter.com/3WDmTeLAHF t.co/Yw7uUpM5vZ
— ²³?????????????☄️?? (@BronGotGame) May 12, 2025I can see the bud, something beautiful is about to come.
In his first three seasons in the NBA, Derrick Rose hit the ground running.
In year one, he won Rookie of the Year, averaging 17 points and six assists. The Bulls made the playoffs and lost in the first round to the Boston Celtics, in a series that went the distance.
Good start.
By year two, he was already an NBA All-Star, averaging 21 points and six assists. However, the Bulls finished with the same record as the year before, and a worse playoff performance, losing in five games to the Cleveland Cavaliers.
Year three was the absolute peak.
Rose became the youngest league MVP in NBA history, at just 22 years old. A feat so big that even the undisputed GOATs of the sport couldn’t do it. He averaged a career-high 25 points and nearly eight assists. His Bulls finished 62–20, a 21-win improvement from the year before.
In the playoffs, they won round one in five games, round two in six, and found themselves in the Eastern Conference Finals against the LeBron James, Dwyane Wade, Chris Bosh–led Miami Heat.
“When he was ruling the East, I had nothing but respect and a humble fear going against D-Rose,” said LeBron James.
Chicago lost in five, but they had a 22-year-old MVP who was only going to get better, and they were just three wins away from the NBA Finals.
They could almost sniff it.
When 22-year-old Derrick Rose became the NBA's youngest-ever MVP!#TeamDay | @chicagobulls pic.twitter.com/BiCUMn3hu0
— NBA TV (@NBATV) August 21, 2019The Rose, just, never blossomed.
D-Rose played with a ton of explosiveness. Great for the eyes. Not so great for the knees.
And he played in the Tom Thibodeau style of basketball, a style that required every starter to essentially play every single minute, even if your team was up 100 points. There were no garbage minutes in his vocabulary. A risky approach, one that did not age well at all.
In a lockout-shortened 2011–12 season, Rose began to miss time.
It started less than two weeks into the season, when Rose fell hard enough on his elbow to warrant X-rays. The X-rays were negative, but it began an ugly trend. Less than a week later, a collision left him with a sprained left big toe that forced him to miss his first game of the season. He returned three days later, despite persistent pain. He played just two more games before the pain became too much, forcing him to sit out the next four.
© Mike DiNovo-Imagn ImagesAnd then again, ten games later, Rose missed more than a week with back spasms. He came back, played another eleven games, before reports surfaced of a groin strain that kept him out. He returned for one overtime game against New York, then missed another with a sprained right ankle. To end the season, he missed even more time with a right foot injury.
Still, the Bulls made the playoffs with a 50–32 record, taking on the Philadelphia 76ers.
In Game 1, the Bulls were dominant. Up twelve with one minute left, the game was over. There was no realistic way the Sixers could come back, and any sane coach would have pulled the starters.
But that wasn’t Thibodeau’s style.
Rose, who had already missed significant time that season, was still on the floor, with 37 minutes logged. There was no reason for him to be out there anymore.
D-Rose had the ball at the top of the key. He got a screen from Noah. One dribble. Legs that still looked fresh and bouncy. A euro-step–esque jump stop, landing on both legs, and pushing off with one.
And the worst thing that could have happened, happened.
“Uh-oh, uh-oh—Rose came down bad on his left foot! See him? Holding onto his knee. Holding onto his knee and down,” said Kevin Harlan, words that still ring in the ears of Chicago fans everywhere.
The most painful moment in #Bulls historyThe entire city of Chicago froze the moment D Rose tore his ACL. pic.twitter.com/umt6SAs5Lf
— Die-Hard Chicago Bulls Fans (@Bullsfans) October 2, 2024Rose tore his ACL in the final minutes of a game that was essentially garbage time.
One of the greatest primes in basketball history was stolen by an irrational game plan, one that still makes no sense to this day.
The soil is barren.
D-Rose missed the entirety of the 2012–13 season. That year, Chicago still won 45 games and lost in the second round of the NBA playoffs.
If Rose was there, we would’ve… The thought everyone had. The thought no one finished.
In the 2013–14 season, he played just ten games. Chicago finished with 48 wins and now had the second-best defense in the NBA. Joakim Noah won Defensive Player of the Year and made All-NBA First Team. And this 24-year-old shooting guard, drafted with the last pick of the first round, Jimmy Butler, was starting to look promising.
Chicago, without Rose, lost in five games in the first round.
In the 2014–15 season, D-Rose played 50 games. He still missed time with injuries, but it was the healthiest he had been in years. That offseason, the Bulls signed Pau Gasol, Kobe’s running mate, bringing championship DNA with him. Sure, he was 34, but he was still an All-Star that season and made All-NBA Second Team.
Chicago also brought in a 24-year-old power forward, Nikola Mirotić, who had been lighting it up in Europe and finished second in Rookie of the Year voting. The Bulls also had three players in contention for Sixth Man of the Year. The team was deep.
And on top of all of that, Jimmy Butler won Most Improved Player, made the All-Star team, and earned All-Defensive honors—a breakout at exactly the right time.
Was this the year the Bulls won it all?
© David Richard-Imagn ImagesThey won Round One in Milwaukee, 4–2. In Round Two, Rose was back, facing LeBron and his new running mates in Cleveland. Chicago stole a game in Cleveland and came back home with the series tied 1–1.
Chicago needed Game 3. A chance to take a 2–1 lead. A chance to finally push LeBron aside.
The score was tied, 96–96.
Three seconds to go. Who gets the ball?
The former MVP, fighting his way back from injuries? Or the reigning Most Improved Player, in the middle of a breakout season?
The Cavs defended hard, forcing the Bulls to use nearly all five seconds just to inbound the ball. Rose found a sliver of space, caught it, took two dribbles, and got switched onto LeBron James with 1.9 seconds on the clock.
Rose was never a great three-point shooter. In fact, he had the worst percentage on the Bulls, 28%.And yet, he rose up, no pun intended, over one of the greatest players of our generation, nearly half a foot taller than him, and took the lowest-percentage shot he could possibly take.
And he banked it in.
Mike Breen yelled “Bang,” and the Bulls went up 2–1—followed by one of the most iconic Derrick Rose celebrations imaginable.
That’s where I wish Rose’s movie ended. On that shot. And nothing more.
"Rose trying to get open… fires away… BANG!"Before the Bulls raise his #1 jersey to the rafters Saturday night, take a look back at Derrick Rose's iconic game-winner vs CLE in Game 3 of the 2015 Eastern Conference Semifinals ? pic.twitter.com/nCNfCQpagG
— NBA (@NBA) January 23, 2026I don’t want to remember that the Cavs went on to win the series. Or the day Rose found out he was being traded to New York. Or the emotional 50-point game in Minnesota. Or how he reinvented himself as a sixth man and bounced around the NBA before retiring.
I don’t want to remember any of that. Not today. Not ever. But I do want to remember everything else he did for Chicago.
© Mike DiNovo-Imagn ImagesDerrick Rose: The Kid from Chicago
Derrick Rose was the first real ray of light Bulls fans had seen since Michael Jordan’s dynasty ended. The shadow that dynasty cast was so wide that no one truly believed someone could fill it.
Years earlier, the Cavaliers landed the number one pick and selected a hometown hero in LeBron James. Chicago believed they were handed the same script with Rose and the first overall pick. Yes, the Bulls had drafted first overall before, Elton Brand, but he did most of his damage in a Clippers jersey.
It’s not like Chicago was deprived of basketball talent. From George Mikan, the league’s first superstar in the 1940s and ’50s, to Isiah Thomas, to Dwyane Wade, and even Anthony Davis. But none of them did it in a Bulls jersey. (Wade’s time with the Bulls doesn’t count. Nobody wants to talk about that.)
Rose’s high-flying style of play, being a hometown hero, and the fact that he never seemed like a guy who took his fame for granted made him incredibly easy to root for.
“When you come to a basketball game and it’s time to compete and you rise up to the highest level in our sport, you’re a mythical figure,” said Hall of Famer Isiah Thomas. “And for us, what Derrick Rose represents, and what he still represents, is that you can overcome the struggle. Not only can you overcome it, even when you get knocked down, you can still get up and walk. That’s what Derrick Rose is for all of us.”
Rose was relatable. Pooh—that’s what they called him, out of love. Named after a character that practically defines lovable. You could see him walking down the street like any other Chicagoan. And if you greeted him, he wouldn’t look down on you.
@houseofhighlightsDrose just chilling in the city ?(@jodygtv ) #derrickrose #drose #nba #chicagobulls
♬ original sound – House of HighlightsHe appreciated the love the city gave him, even if he never led them to the promised land. And it’s because he tried—through injuries—and cried with the fans when the team let him go.
Rose has always been a part of the community, something that’s been emphasized in the lead-up to his jersey retirement. Not a single story told makes you feel like he doesn’t deserve it.
Yes, you can argue the longevity, the accolades, the availability, and his Hall of Fame probability. But you can’t deny his impact, his legacy, and the love the world of basketball, and Chicago, has for that man.
Congratulations, Pooh. You deserve it.
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