6 most painstaking ‘What Ifs’ from Derrick Rose’s Bulls tenure, NBA career


It’s been fun reliving some of the most exciting moments from Derrick Rose’s Bulls tenure during Derrick Rose Week on NBC Sports Chicago.

But for every fond memory Rose was party to, there are countless open-ended questions, What Ifs and half-fulfilled hopes. The full picture is what makes Rose’s story one of the greater modern sports tragedies.

Still, with the sports world paused (though gaining momentum towards returning), what better time to ponder the unanswerable hypotheticals of Rose’s career than now?

We took a look at, and further examined, six especially painstaking What Ifs from Rose’s time in Chicago and beyond. Here goes nothing:

What if the Miami Heat’s Big 3 assembled in Chicago?

An oldie, but undeniably a goodie. The temperature on this one amplified even further when Dwyane Wade directly addressed rumors that he and LeBron James very nearly set up shop in Chicago in an interview with Vincent Goodwill back in 2016.

“I know LeBron’s eyes were here. I know my eyes were here,” Wade said, then a member of the Bulls, but a half-decade too late.

That quote, and the rest of Wade’s comments, are likely coated in revisionist history. But even at the time, there were reasons for him, James and Chris Bosh (if possible) to team up with the Bulls. 

For Wade, it was a chance to come home. For James, it was a surefire opportunity to string together championships in a massive market while also playing under a coach James so venerated that he reportedly requested a second meeting with Tom Thibodeau after meeting with the Bulls in the summer of 2010. For Bosh, it was anywhere that wasn’t Toronto.

And there’s reason to believe the master plan was financially feasible, as well. Between Rose, Joakim Noah, Taj Gibson, James Johnson (all on rookie deals), Luol Deng, Kirk Hinrich and their impending first round pick, ESPN’s Kevin Arnovitz projected the Bulls to have $31.85 million committed entering the summer of 2010 — a year in which the official cap landed at $58.044 million. Flipping Hinrich, who was owed $9 million in 2010-11, and that impending pick (Kevin Seraphin, ~$1.6 million) for cap space dragged that figure down even further. Combine that with a potential trade of Luol Deng (~$11.3 million) to the Los Angeles Clippers that was reportedly in the works, and the Bulls could have conceivably freed up almost $50 million in cap space for that offseason. The Heatles eventually signed in Miami at a discounted rate for contracts that, in Year 1, paid them a combined $43.2 million.

(And before you say it, yes, Rose took part in the recruiting effort. Sunny South Beach just won out.)

There are a few leaps in the above paragraph (for one, would that discount have also applied in blustery Chicago?), but a hypothetical starting five of Rose, Wade, James, Bosh and Noah, with Gibson and bargain barrell vets off the bench, exceeds even video game levels of preposterousness. It’s fun to ponder.

Had all the principles come together, how many more banners might be hanging in the UC rafters today?

Somewhere from two-to-four feels a reasonable estimate. Superteams often take time to gel — the Big 3 Heat won just eight of their first 17 regular season games and sputtered out in the 2011 Finals — and a Rose-Wade backcourt, specifically, might have experienced growing pains. But a run of historic proportions would have been inevitable with that level of talent, the quintessential point forward in James and a versatile, low-usage, defensive stalwart frontcourt of Bosh and Noah. 

Without another true contender in the East outside of the depreciating Big 3 Celtics, four straight Finals berths feels a lock, and a team of that caliber would have certainly at least matched the Heat’s two chips in those chances. 

But, also similar to the Heat, the group disbanding in 2014 — when Wade, James and Bosh all negotiated opt-outs in their contract — would be a near certainty, too. So is the way of the current NBA.

What if Tom Thibodeau had subbed Rose out in Game 1 of the 2012 Eastern Conference first round?

On rewatch, the first thing that pops off the screen from the play that resulted in Derrick Rose’s first torn ACL is the scorebar.

Chicago Bulls 99. Philadelphia 76ers 87. Fourth Quarter. 1:25 remaining.

That’s in Game 1 of the 2012 Eastern Conference first round against an eighth-seeded 76ers team, a game in which the Bulls had led by as many as 20 points with 4:36 remaining. Last point aside… What in the world was Rose doing in that game? 

Trying as hard as possible to suspend hindsight for a moment, this one cuts both ways. Rip Hamilton articulated the get-your-best-player-the-hell-out-of-a-game-you-have-locked-up argument well in a recent appearance on the All The Smoke podcast:

“I won before in Detroit, I’d been on the bench at times where, you know, we had the opportunity to go after that record, or winning 70 games or whatever cause we were killing during one year,” Hamilton told hosts Matt Barnes and Stephen Jackson. “And guys like ’Sheed (Rasheed Wallace) and Ben (Wallace) would be like, ‘Man, get Chauncey (Billups) off the floor. Get Rip off the court.’ Or they’d call timeout and get us off the floor. Because we knew that it’s bigger than just that game…

“Once you got the game in hand, especially in the playoffs, you gotta get your best player off the floor. You just have to,” he continued. “And I’m thinking to myself like, ‘C’mon Thibs (Bulls coach Tom Thibodeau). Gotta get him out the game.’”

That Rose missed a combined 27 games in the lockout-shortened 2011-12 season with five separate injuries should only have added to the emphasis on keeping him bubble-wrapped whenever possible. Especially for a team with championship aspirations.

Or, maybe shaking off that rust was a reason to keep him in, along with those Bulls’ propensity to unravel late in playoff games against premium competition. A collapse after holding a 12-point lead with under four minutes left in Game 5 of the 2011 Eastern Conference finals punctuated a series in which the Bulls shot 32% from the floor in fourth quarters and overtimes, and allowed 48% shooting by Miami, respectively. Evidently, Thibodeau thought any and all reps were valuable to this team.

The night of Rose tearing his ACL, here’s what Thibodeau told reporters:

“I don’t work backwards like you guys do. The score was going the other way. He’s got to play,” Thibodeau said. “He’s got to work on his closing. That’s what I was thinking.”

Whichever side you ascribe to ultimately matters little. It happened. But had it not, what would the Bulls’ fortunes have looked like for the remainder of the 2012 postseason?

RELATED: Tom Thibodeau thinks Bulls would've won a title if Derrick Rose stays healthy

Before any Finals aspirations, a second-round series with a red-hot — albeit aging — Celtics team still constructed around Paul Pierce, Kevin Garnett and Ray Allen would have loomed. That Celtics team took the Heat to seven games in the 2012 Eastern Conference finals of our reality, but let’s assume a healthy Rose finding his footing spearheads a six- or seven-game series win, given the Bulls’ superior talent and homecourt advantage.

That would bring up a second consecutive Eastern Conference finals matchup with the Heat, the only team to enter that postseason with better title odds than the Bulls. 

The Bulls would surely have been more equipped to compete with the Heat in 2012 than 2011 if Rose was able to find his way back to form. That offseason, the Bulls had swapped Keith Bogans for Hamilton at the starting shooting guard spot, and such key cogs as Taj Gibson, Omer Asik and C.J. Watson, among others, were a year older and wiser. As the deeper team with homecourt advantage, and facing a Heat squad that hadn’t yet reached the pinnacle as a unit, this would have represented the Bulls’ best shot at a chip.

But depth vs. top-end talent matchups, as Bulls fans know too well, typically skew towards the latter in the postseason. Miami would have boasted three of the top five players in the series, at least — depending on your view on the Noah-Bosh debate

Perhaps the Bulls would have taken more than one game this go-around. But James’ Game 6 obliteration of a Celtics team that was purported to have broken him in the actual 2012 Eastern Conference finals was indicative of a man at the peak of his powers on an unobstructionable mission. He wasn’t being denied that year.

If the Bulls could have found their way around that immovable force, their chances against the budding-but-still-not-quite-there Oklahoma City Thunder in the Finals would have been favorable. But for the 2012 playoffs — healthy Rose or not — the Heat probably still reign champions.

But it does invite the inevitable, “What if the injuries had never piled up for Rose?” quandary. That is a thornier one, without one incident to pinpoint outside of Game 1 of the Philly series. As mentioned, the run-up to his infamous jump stop featured five different injuries throughout the 2011-12 season. Then, after sitting out the 2012-13 campaign to rehab the first ACL injury, he tore the medial meniscus in his right knee just 10 games into his 2013-14 return. He tore that same meniscus again midway through the 2014-2015 season.

It’s too many variables to pick at. But I’ll just leave these nuggets as indicators of the trajectory he was on before April 28, 2012:

  • Rose is one of 11 players in NBA history to notch at least 5,800 points and 1,900 assists in their first four seasons, even with his 2011-12 campaign truncated by injuries and the lockout. The company is good.

  • He and Oscar Robertson are the only two players in NBA history to log a season of at least 2,000 points and 600 assists before age 23.

  • Youngest MVP ever. Tied for rookie record for most points in a playoff debut (the company is pretty good there, too). Three All-Star games by age 23.

Assuming steady improvements through his prime, the best case is a pantheon-level all-time point guard. The worst case (barring injury) is in all likelihood a surefire Hall-of-Famer (on the strength of the MVP and counting stats alone) that never quite got over the championship hump, but would be remembered for his unheard of talent.

What if the Bulls moved decisively on a backcourt-mate for Rose in 2011?

The 2012 postseason stands as the single biggest Bulls-based What If of the 21st century. That doesn’t feel an outlandish statement.

But what if the championship hopes of a city never had to ride on that cramped-scheduled, injury-riddled campaign resulting in glory? What if the Bulls had moved faster to fill out a championship cast around Rose in his MVP year and mitigate the risk of the aforementioned five-game defeat to the Heat in the 2011 Eastern Conference finals?

It’s hard to gripe too much with the construction of the 2010-11 squad. Rose, Deng and Noah in their 2011 iterations represented a title-contender-caliber core. The Carlos Boozer signing panned out. Gibson (then a rookie), Asik, Korver and Watson, among others, were well-cast. They were a deep unit that finished the regular season No. 2 in both defensive and net rating, No. 1 in the most important of all statistics, win-loss record, at 62-20, and had the league’s MVP.

The most glaring hole on the roster all season and throughout the playoffs, though, was at shooting guard, where the hard-nosed but generally anemic Keith Bogans started, supported by Korver and Ronnie Brewer off the bench. Along with the Bulls’ fourth-quarter foibles, it was the biggest weakness the Heat exploited in their convincing Eastern Conference finals victory.

The absence of a plus-backcourt mate also put undue pressure on Rose, who finished his 16 games that postseason averaging 23.5 shots per game and with a whopping, NBA-leading 35.2% usage rate.

And this wasn’t an under-the-radar issue, even from the Bulls’ side. Rumors flurried at the 2011 deadline in regards to their pursuit of a starting two-guard. Adrian Wojnarowski, then of Yahoo! Sports, reported the Bulls offered a first-round pick to the Houston Rockets in exchange for Courtney Lee, but Asik proved a sticking point in negotiations. There were also reports of the Bulls exploring turning a Brewer-plus-picks package into O.J. Mayo. 

Lee, specifically, would have been a splendid fit alongside Rose. At the time, he was a more-than-capable wing defender, sharp long-range shooter (nine years later, he’s still a 38.8% 3-point shooter for his career) and effective slasher. And all of virtues wouldn’t have come at the expense of the offense running through Rose.

Is he the difference in that Heat series? Maybe not. But the Bulls stood pat, and we’ll never know. But, frankly, it’s hard to beat up John Paxson and Gar Forman too much for this one. Based on reporting from the time, any of the above trades (or others that were speculated) would have required parting with at least Gibson or Asik, and at the time of the deadline, Joakim Noah was sidelined for an extended period following serious thumb ligament surgery. Frontcourt depth was a need.

Still, if the Rose era taught us anything, it’s to not take time for granted. The Bulls had a championship window, and didn’t fully seize it — in all likelihood, content to let the chips fall how they may and, worst case, be set up for sustained success in the future. Unfortunately, that never came to pass. And hindsight is 20/20.

What if David Blatt had gotten his timeout off?

It’s the Hue Hollins blown call of our generation.

With 8.4 seconds remaining and the score knotted 84-84 in Game 4 of the 2015 Eastern Conference semifinals, Cleveland Cavaliers coach David Blatt attempted to call a timeout from his bench to advance the ball to midcourt after a Derrick Rose layup.

Only he didn’t have a timeout in his pocket.

Had the referees seen Blatt’s signal before assistant coach Ty Lue yanked him off the floor, the Cavs would have been assessed a technical, and the Bulls would have received one free throw and possession. Victory wouldn’t have been certain, but chalk it up as likely.

But the officials didn’t see it. Instead, LeBron James scurried up the floor, had a layup blocked out of bounds with 1.5 seconds left, and then, on the ensuing inbounds play, knocked down a baseline jumper over Jimmy Butler at the buzzer that gave Cleveland an 86-84 victory and drew the series level 2-2. It was the second game-clinching buzzer beater at the UC in three days, after Rose gave the Bulls a 2-1 series lead with his famed long-distance banker in Game 3.

The Cavaliers went on to win the next two games and the series. Pau Gasol, after leaving Game 3 with a hamstring strain, missed the final four contests. Cleveland made the Finals, and fell to the Golden State Warriors in six games.

But could things have been different if the Bulls had stolen Game 4? At the time, only 10 teams in NBA history had ever overcome 3-1 postseason deficits. The Bulls were without Gasol, but the Cavs were without Kevin Love. The Bulls would have needed to win only one of their next three games, and they had one game at the United Center in hand.

Given James’ history against the Bulls (and overcoming 3-1 deficits), it’s tempting to concede him the benefit of the doubt here. But maybe he doesn’t climb the mountain this time. Maybe the Bulls steal one last game from James, Kyrie Irving and company, oust an overrated Atlanta Hawks team in the Eastern Conference finals (not outrageous) and make it to their first NBA Finals since the Jordan years for a date with the fresh-faced Warriors.

The Cavaliers sans Love and Irving took the Warriors to six that season. It’s fair to assume that the Bulls could have put up a similar fight (they were 1-1 against them in the regular season), if not topple them entirely — think of the alternate dimension dominoes that would set off.

In the spirit of objectivity: I’m still probably taking the Warriors in that Finals — if the Bulls even could have made it that far. But ultimately, Blatt’s postgame remarks summed it up best.

If only he had.

What if Carmelo Anthony had taken his talents to Chicago in the summer of 2014?

Also folded into that 2015 postseason is the question: What if the Bulls had nabbed Carmelo Anthony in the summer of 2014? It was rumored at the time, and to this day, parties involved maintain it was in the realm of possibility. 

Here’s what Anthony, himself, recently told our K.C. Johnson in November 2019 on this matter:

I just think that playing against those guys over the years and knowing the guys they had on those teams and knowing how hard those guys really worked, I was trying to see where I could fit in that. They were always missing one or two pieces with that team. We used to always talk about, ‘Man, that’s a team I could see myself playing for.’ … They were very impressive with their pitch. Everything about it — the organization, the players, Coach Thibs, the front office, ownership — was exciting. But I chose to stay home (with the New York Knicks).

He also told ESPN in August that he was "going to Chicago," even though the Bulls couldn't match the Knicks' monetary offer, before back-door whispers pushed him away. 

It certainly would have been something, a big three centered around Rose, Jimmy Butler and Anthony, with Noah, Gibson and a stable of competent role players to supplement. 

But ultimately, how the ball-dominant Anthony would have meshed with Rose and Butler, whose star was burgeoning at the time, is unclear. The Bulls recovered deftly from Anthony spurning them by signing Pau Gasol, who made two All-Star teams in two seasons in Chicago, and Nikola Mirotic (who wasn’t a solid contributor until later on) to provide spacing off the bench. The Knicks, meanwhile, amassed an 80-166 record from 2014-2017 before flipping Anthony to Oklahoma City in the middle of a five-year, $120 million contract that fast became bloated.

Could Anthony have been the difference in the Cleveland series (and thus, the postseason in general)? It’s possible, considering Gasol and Love’s injuries, and the Bulls’ ability to throw Butler on James and hide Anthony elsewhere. But given Gasol’s stellar play in Chicago (17.6 ppg, 11.4 rpg, 3.4 apg in his tenure on stellar efficiency) this one probably doesn’t keep many up at night in the same way others on this list do.

Plus, Anthony made his way to the Bulls eventually. All’s well that ends well, right?

What if the Lakers (or another contender) had traded for Rose at the 2020 trade deadline?

A quick, but fun, one to wrap up. What if the Detroit Pistons chose to parlay Rose’s resurgence (he averaged 18.1 points and 5.6 assists for them in the abridged 2019-20 season) into assets at February’s deadline? 

And what if said parlay had resulted in Rose donning the Lakers’ purple and gold? According to Shams Charania, the Lakers, in need of perimeter shot creation, offered a package centered around Alex Caruso and draft compensation, which the Pistons sniffed at.

It certainly would have been an uncomfortable sight for Bulls fans, at first, especially given Rose’s unceremonious history playing alongside LeBron James during his six-month spell with the Cavaliers in 2017-18.

But it also certainly would have given Bulls fans an extra couple layers to engage with during the NBA’s unprecedented 22-team regular season resolution in Orlando, Fla. A potential title run with the Lakers, one of the two consensus title favorites and certainly the leader in the clubhouse to make it out of the West, would only bolster Rose’s currently checkered Hall of Fame case. A hypothetical matchup with an invigorated Joakim Noah and the Los Angeles Clippers in the Western Conference finals would have been equal parts gripping, heartwarming and conflicting.

In our current reality, we can only hope to see Rose suit up if some round of televised scrimmages crop up for those teams left out of the Disney experiment. Less fun, but perhaps more fitting.

RELATED: ‘I’ll Show You’ Excerpt: Why Derrick Rose wants son PJ to be like Joakim Noah

NBC Sports Chicago will honor the Bulls great with “Derrick Rose Week presented by Saint Xavier University” starting up Monday, June 8 at 7:00 PM CT with the first of five-straight nights of “Classic” game performances. See full schedule here.

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