10 Biggest What-Ifs In NBA History: Michael Jordan Would Dominate With The Trail Blazers

• These “What If” scenarios would have changed NBA history as we know it today

• Len Bias was selected second overall in the 1986 NBA Draft by the Boston Celtics but passed away just two days later

• Most of the what-if scenarios below involve draft decisions or trades that nearly went through

One of the greatest and most polarizing discussions between basketball fans are the ones that occur surrounding classic what-if scenarios. You know the scenarios I am talking about. The discussions are great to have amongst your peers and within the NBA community. The ones that make us think about the alternate universe we could be living in if things surrounding each of these what-ifs changed even in the slightest way. 

What if this player never got injured? What if this team drafted this superstar instead of the bust they wound up with? What if this team pulled the trigger on a trade that would have changed their franchise history forever? What if the league didn’t step in and prevent things from happening? We have all had these conversations before, and we all have different opinions on what would have occurred.

Today, I will be giving you my opinion of the 10 greatest what-if scenarios in NBA history and how I think things could have played out. It is important to remember that we are going to differ in our opinions on these scenarios, and there is absolutely no way to prove what you or I say is actually what would have happened if they had played out differently.

Here are the 10 biggest what-ifs in NBA history.

Honorable Mentions

What If Derrick Rose Was Never Injured?

Right out of the gate, we get things started off with a what-if scenario that has been discussed ad nauseam. In the early 2010s, Derrick Rose catapulted himself to stardom by becoming the youngest MVP in NBA history and consistently having the Bulls at or toward the top of the NBA standings. Rose’s athleticism and skill were incredible to watch, and all of us thought we were seeing one of the greatest point guards in NBA history evolve before our very eyes.

Sadly, those feelings would not last. In a first-round playoff matchup against the 76ers, the Bulls had a large lead late in the fourth quarter of Game 1. Inexplicably, Rose remained on the court even though the game was all but over. As he prepared to make a cut and leap to the basket for a layup, Rose went down in agony, tearing his ACL. After missing the entire 2012-13 season, Rose returned in 2013-14 only to tear the meniscus in his opposite knee. From that point forward, he was never the same again.

It is hard to imagine what could have been if Rose never suffered these injuries. I do think at least one more MVP award would have been in his future, along with an NBA championship for the Bulls which they have been longing for since the departure of Michael Jordan in 1998. This injury changed NBA history as Rose’s career was on a path toward becoming a top-10 point guard ever, and top-five wasn’t out of the question either. Rose is still one of the most beloved players in the NBA today. It just would have been nice for all of us to see his true potential reached.

What If The Orlando Magic Signed Tim Duncan And Created A Superteam?

Tim Duncan is the greatest power forward and one of the greatest players in NBA history. Duncan led the San Antonio Spurs to five NBA championships in his career, won two MVP awards, and three Finals MVP awards as well. Did you know that all of that was nearly done in an Orlando Magic uniform instead?

Back in 2000, Tim Duncan would hit free agency for the first time in his career. Duncan, taking his time with his decision, was supposedly extremely interested in joining the Orlando Magic, who already had Tracy McGrady and Grant Hill as their shooting guard/small forward combo. At the time, McGrady was just leaving the Raptors for the Magic, where he would go on to become one of the best players in the game and a back-to-back scoring champion in 2003 and 2004. Hill, who shared an agent with Duncan at the time, was coming off the first of many injuries that would hinder the rest of his career in his last year with the Detroit Pistons.

Ultimately, Duncan would return to the Spurs, where he continued to build his legacy as one of the greatest players ever. Apparently, the reason why Duncan ultimately went back to the Spurs is because Magic coach Doc Rivers told Duncan that family members were not allowed on the team’s plane, and he was not going to change the rules for anyone.

The Big Three of Duncan, McGrady, and Hill would have been a truly special site for basketball fans. There is no doubt in my mind that any team led by these three stars would secure multiple NBA championships. Duncan and McGrady could have gone down as a top-10 duo in the history of the NBA. Instead, the Spurs would become a dynasty, and Orlando still seeks their first NBA championship as a franchise. Thanks a lot, Doc.

What If The Golden State Warriors Traded Stephen Curry To The Milwaukee Bucks?

Back in 2012 and 2013, we had yet to see either Stephen Curry or Giannis Antetokounmpo reach their true peaks as NBA players. Curry was still somewhat finding his way with the Warriors, while Giannis hadn’t even broken into the NBA just yet. At the same time, the Warriors were desperately in need of a big man to take them to the next level and had their eyes on Andrew Bogut of the Milwaukee Bucks. With a logjam at guard with Stephen Curry and Monta Ellis sharing the backcourt, one of them had to go to make the deal go through.

Originally, the Bucks wanted Curry, but Milwaukee’s team doctors ultimately nixed the trade due to concerns over the ankle injuries that had plagued him in his early days. Eventually, the Warriors would acquire Bogut for Ellis, Ekpe Udoh, and Kwame Brown. Just two years later, Curry would go on to win his first MVP and first NBA championship with Golden State while the Bucks waited for Giannis to develop and eventually got their own title in 2021.

If the Curry deal had been approved, there are multiple scenarios on each side of the spectrum that could have played out. The first is yes, the Bucks could have had an absolute superstar duo of Stephen Curry and Giannis Antetokoumpo as they hit their prime and ran the league with multiple titles. The other is that Curry’s development never happens due to Milwaukee not allowing him to play the way Golden State has. Maybe Giannis doesn’t develop the way he does due to Curry’s presence. Either way, the course of NBA history would have been changed forever.

10. What If Len Bias Never Passed Away?

In 1986, Len Bias of The University of Maryland was touted as one of the nation’s top basketball players and a guaranteed lock for a top-three pick in the upcoming NBA Draft. He would be selected second overall by the Boston Celtics, and the prospects of him joining a team already loaded with Larry Bird, Kevin McHale, and Robert Parish had the NBA World buzzing. Unfortunately, not even 48 hours later, Bias would tragically pass away in his college dorm room of a cocaine-induced heart attack.

The death shocked the entire nation as Bias was supposed to be the next great rival to Michael Jordan and other greats in the game at the time, he was that damn good. There is even a great possibility that with Bias’ arrival in Boston, maybe the Bulls aren’t the team that ran the 1990s, but Boston led by Bias. The rivalry with Jordan could have been the next Magic Johnson/Larry Bird-type rivalry, as these two would undoubtedly see each other year after year sharing the same conference. Bias’ death is one of the most tragic occurrences in NBA history, and we all wish it was far more than a what-if scenario.

9. What If The Phoenix Suns Drafted Luka Doncic Instead Of Deandre Ayton?

In 2018, the Phoenix Suns owned the first overall pick in the NBA Draft for the first time in franchise history. As they looked around at the draft pool and went over their team needs, they decided a big man was most important and selected Deandre Ayton from the University of Arizona. Now, Ayton has not been bad with the Suns by any means over the last five years averaging 16.7 points and 10.4 rebounds for his career and helping lead them to the 2021 NBA Finals. However, there was a future NBA superstar taken just a few picks later that perhaps could have won them their first NBA title.

That future superstar would be Luka Doncic from Slovenia, who has been an MVP-caliber player pretty much from his rookie season on. What would have happened if Phoenix selected Doncic instead of Ayton? Well, a lot, actually. I truly believe that the Suns would have been 2021 NBA champions if Doncic was leading the charge instead of Chris Paul. I also believe that they would have had more than one by now, given the talent they have been able to bring in around their stars.

I also believe there is no way Kevin Durant and Bradley Beal would be in Phoenix right now, considering Doncic ended up earning a supermax extension in no time with Dallas. We wouldn’t have the fierce rivalry between Luka Doncic and Devin Booker, as they would be teammates taking over the NBA one game at a time. The Mavericks would probably be the only thing that remained the same, just with Trae Young as their point guard instead of Luka. Talk about a rift in the space-time continuum.

8. What If The Detroit Pistons Drafted Carmelo Anthony Instead Of Darko Milicic?

In the 2003 NBA Draft, there was a massive group of world-class athletes, future champions, future MVPs, and future Hall of Famers available to all 30 NBA teams. Of course, nobody knew what any of these players would turn out to be, but hindsight is always 20/20, right? In this case, the Detroit Pistons owned the second overall pick after LeBron James was locked-in as the first pick to Cleveland. 

With that selection, they decided to take Darko Milicic out of Serbia, a 7-footer who had been highly touted by scouts during the draft process. And, the Detroit Pistons made one of the worst mistakes in their history.

Milicic would go on to be one of the worst draft busts ever, yet played 10 seasons in the NBA, averaging 6.0 points and 4.2 rebounds for his career. Right behind Detroit, the Denver Nuggets would select Carmelo Anthony, a future Hall of Famer and one of the top scorers in NBA history. Of course, Detroit would go on to win an NBA championship the season immediately following this draft in 2004, so the decision wasn’t a complete disaster, but what if Anthony was their choice instead of Darko?

Well, there are, again, a few scenarios that could have happened. The first is that Anthony comes to Detroit, wins a championship as a rookie, and his legacy is completely reshaped, and he is no longer viewed as a ringless player. However, would Detroit still have traded for Rasheed Wallace that season, who became a big part of the Pistons’ championship run? Would Anthony have hurt the Pistons with his offensively-driven mindset? Would the Pistons have turned Carmelo into a completely different beast on the defensive end? Those are questions many do not think about in this situation.

7. What If The Minnesota Timberwolves Didn’t Pass On Stephen Curry Twice In The 2009 NBA Draft?

The Minnesota Timberwolves have a long and cringe-worthy list of mistakes they have made in the NBA Draft over the course of their team’s history. None of them are bigger than the blunder they pulled off in 2009. In the 2009 NBA Draft, the Timberwolves owned both the fifth and sixth overall picks, desperately searching for their next star to turn the franchise around. With the fifth pick, they selected Ricky Rubio out of Spain, who would take two years off in Spain before joining the team in 2011-12. With the sixth pick, they selected Jonny Flyyn, who played three years in the NBA before heading overseas to finish his basketball career.

Right after those two picks, the Golden State Warriors selected Stephen Curry, and the rest is history as we know it. Nobody in their right mind at the time knew Curry would eventually change the game of basketball as we know it, win four NBA championships, and become the greatest shooter the game has ever seen. However, if he had gone to Minnesota, none of that may have happened. Who is to say Minnesota doesn’t completely change how Curry plays the game? Who is to say Curry becomes a superstar without the guidance of Steve Kerr and Mark Jackson? At the same time, who’s to say that Curry doesn’t change the Timberwolves franchise around and win them four NBA titles? Either way, the game, and its history would look far different than it does today.

6. What If The Portland Trail Blazers Drafted Kevin Durant Instead Of Greg Oden?

For the last 46 years, the Portland Trail Blazers have done whatever they can to try and return to the top of the NBA as champions. As much as they have done right, they have also had some colossal missteps that have prevented that from happening. One such misstep occurred in the 2007 NBA Draft when they owned the first overall pick.

With that pick, they decided on talented big man Greg Oden from Ohio State University. Unfortunately for Portland, Oden would miss his entire rookie season and play just a total of 82 games in six years due to knee and foot injuries that shelved him for seasons at a time. Looming behind him with the second overall pick was one of the greatest scorers in NBA history, Kevin Durant. Over the years, Durant has become one of the most efficient players ever while winning four scoring titles, an MVP, two NBA titles, and two Finals MVPs with the Thunder, Warriors, Nets, and Suns.

Now, imagine this. If Portland had decided to take Durant, they would have had a trio of him, Damian Lillard, and Brandon Roy take the floor together. Of course, Roy would be gone soon due to early retirement, thanks to knee issues. However, that still leaves Portland with Durant and Lillard, which could go down as one of the greatest duos ever. Personally, I think they would have been a tougher matchup for Miami in 2012 than Oklahoma City was for Miami in the NBA Finals, and I believe they get past the Warriors in 2016 as well.

5. What If The Golden State Warriors Traded Stephen Curry And Klay Thompson For Chris Paul In 2011?

Back in 2011, Chris Paul was one of the two best point guards in the entire NBA with the New Orleans Hornets. As great as his individual game was, the Hornets were far from a championship contender. Growing frustrated with the organization, Chris Paul requested a trade out of New Orleans. The kicker was, Paul had a no-trade clause and could control where he went, which became important to the outcome of this what-if scenario.

In the market for a star, the Golden State Warriors were prepared to send both Stephen Curry and Klay Thompson to the Hornets in exchange for Paul. At the time, Curry was a young player battling ankle issues, and Thompson was a rookie out of Washington. Paul was not prepared to go from one borderline playoff team to another one and nixed the deal quite quickly, stating he would not re-sign with them after the season was over and hit free agency. Paul would eventually be traded to the Clippers and become a fierce rival, and victim, of the Warriors dynasty that won four NBA titles in eight years.

The hilarious thing about this what-if scenario is the fact that all of these years later, Chris Paul, Klay Thompson, and Stephen Curry are all members of the Golden State Warriors in 2023. Paul was traded to the Warriors this offseason in a deal with the Washington Wizards in exchange for Jordan Poole. While we wait and see if the revamped 2023 Warriors can win an NBA championship, what would have been the outcome of this deal so many years ago?

Looking at this deal from today’s standpoint, this could have completely rewritten NBA history. If Stephen Curry and Klay Thompson go on to become the same Splash Bros. that we know and love today and win the Hornets their first NBA championships in history, the Hornets become the dynasty so polarizing amongst fans in today’s modern NBA. Stephen Curry fulfills his own legacy by wearing the same jersey his father did when he played with the Hornets from 1989 to 1998. There are Hornets jerseys everywhere with their names on them. Michael Jordan looks like a genius as an owner and not a failure if he even buys the team. The rivalry and battle with LeBron James occur in the Eastern Conference playoffs rather than the NBA Finals, and who’s to say they get past him?

The past decade of NBA history could have been completely different had this trade gone through, and nobody would have known it at the time.

4. What If The NBA Did Not Stop The Los Angeles Lakers From Forming A Superteam With Chris Paul And Kobe Bryant?

In December 2011, the NBA was just ending a lockout that stretched 161 days. That same day, the Los Angeles Lakers, New Orleans Hornets, and Houston Rockets agreed to a deal that would send Chris Paul to the Lakers, Pau Gasol to the Houston Rockets, and a group of players that included Lamar Odom to the Hornets. After the lockout, NBA Commissioner David Stern was in no mood to approve a trade after just dealing with the fallout from the long lockout. He vetoed the trade, and it sent shockwaves across the NBA.

The possibility of a Chris Paul and Kobe Bryant duo was beyond the wildest dreams of Lakers fans at the time. Even with a shortened season, Bryant was still in his prime, averaging over 27.0 points per game, while Paul was the best point guard in basketball averaging over 19.0 points, 9.0 assists, and 2.5 steals per game. There is no doubt this duo, along with some other missing pieces, would have delivered at least one NBA championship. We also would have gotten the Kobe Bryant and LeBron James matchup that we never saw in the NBA Finals, finally settling the debate between the two legends once and for all.

As for Paul with the Lakers, he inevitably gets the championship that he has missed out on his entire career. Rather than being seen as one of the greatest ringless players in NBA history, his career finally gets the respect it deserves.

3. What If LeBron James Never Leaves The Cleveland Cavaliers For The Miami Heat In 2010?

From 2011 through 2014, LeBron James, Dwyane Wade, and Chris Bosh led the Miami Heat to four straight NBA Finals appearances and two NBA championships. When they came together in 2010, the trio became the most-hated group in the league, with LeBron James the most hated man on the planet. It was a huge shock to NBA fans everywhere as James held a nationally televised special to announce his departure from the only city he had ever known in the NBA. 

What if James never decided to have this villain arc, though? Frustrated and defeated, part of the reason James went to Miami and teamed up with two other stars is so he actually had the firepower to take down teams like the Celtics. The way things were going, and how they looked moving forward, the Cavaliers weren’t getting any backup for him anytime soon.

If James never leaves Cleveland, there is a tremendous chance that we are not talking about him as arguably the greatest player in NBA history. His longevity may have remained, and there is a good chance he leaves in either 2014 or 2018, as he did with both Miami and Cleveland a second time. There is also the chance that James perseveres and gets through the Eastern Conference anyway with whatever Cleveland provides him with.

2. What If The Charlotte Hornets Never Traded Kobe Bryant To The Los Angeles Lakers?

As everyone can recall, Kobe Bryant began his NBA journey as the 13th pick of the Charlotte Hornets in 1996, straight out of Lower Merion High School in Philadelphia. Bryant had already been tabbed as a future superstar in the NBA and was ready to skip his college days for a shot at the league right away. As Kobe famously recalled, the Hornets had let him know that he “wasn’t needed” in Charlotte. Two weeks later, he was traded to the Lakers in exchange for Valde Divac.

Bryant went on to become one of the greatest players in NBA history with five NBA championships, while the Hornets have yet to even appear in an NBA Finals. Bryant and teammate Shaquille O’Neal became one of the most unstoppable duos in NBA history, winning three straight championships from 2000-2002, and Bryant would help them go back-to-back alongside Pau Gasol in 2009 and 2010.

I cringe when I think about what would have happened if Bryant had wound up with the Charlotte Hornets instead. I don’t see him becoming a global icon in a place like Charlotte, where it would have been much tougher to compete for NBA titles, given the talent around him in his early years. I do still think he becomes one of the NBA’s all-time greats, but five NBA championships in Charlotte seem unlikely, especially with Shaq heading into his peak with the Lakers and teams like Philadelphia and Detroit with much more refined rosters. I think Kobe’s legacy would have taken a massive hit had he never been traded.

1. What If The Portland Trail Blazers Had Drafted Michael Jordan Instead Of Sam Bowie?

Back in the 1984 NBA Draft, the Portland Trail Blazers owned the second overall pick. Hakeem Olajuwon was a lock to go first overall to Houston, and the decision for Portland came down to Sam Bowie, their eventual selection, or Michael Jordan, arguably the best player in the country from North Carolina. With Portland taking Bowie, the Chicago Bulls would take Michael Jordan with the third pick, and you all know what happened next.

The Bulls would go on to win six NBA championships while Jordan became the greatest player in NBA history with six Finals MVP awards, five MVP awards, 10 scoring titles, and many other individual honors to build the greatest resume ever. He even led the Bulls to an NBA title over Portland in 1992. Meanwhile, Bowie was decent but nothing compared to the player Jordan turned out to be, and Portland is still searching for their first championship since 1977 in 2023.

If Michael Jordan had been selected by Portland, it would have paired him with Clyde Drexler on the wings for the Trail Blazers. This would have quite possibly been the greatest two-way duo that ever lived. Jordan never has his playoff rivalry with Detroit. I would guess that Portland even defeated them in the NBA Finals in 1988. The narrative around Jordan’s early career struggles is non-existent, and he remains the greatest player in NBA history to this day. Although, we don’t need an imaginary scenario to confirm that last result. 

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