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The 5 Biggest What-Ifs in NBA History

by Jeremy Block - 11/28/2025

Biggest What Ifs in NBA History Kobe Bryant Shaq O'Neal

There’s always that one game, one play, or one decision in NBA history that leaves fans wondering what could have been. The league is full of heartbreaks, missed opportunities, and moves that have completely reshaped careers and franchises, for better or worse.

But what if things had gone differently? Would the outcome have changed? Time and time again, fans are left to wonder how the league’s biggest “what-ifs” could have rewritten NBA history. So, let’s take a look at five of the most iconic “what-if” stories the league has ever seen. 

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What If Michael Jordan Hadn't Retired in 1993?

Let’s be real: Michael Jordan was already the GOAT before he took that near two-year detour to play baseball. But what if he hadn’t walked away in 1993? Would the Chicago Bulls have stacked eight straight titles instead of just six? After all, they had a better roster than the Houston Rockets, who went on to win the 1994 and 1995 NBA titles.

Jordan thought he’d hit his peak, but in reality, he was just getting started. Retiring at 30, he was putting up 32.6 points, 2.8 steals, and shooting 51% from the field in the 1992-93 season. Love him or hate him, it’s hard to argue that the Bulls wouldn’t have kept racking up the titles. Instead, we got two years of a Jordan-less NBA, and the league had to figure out how to live without its biggest star.

What If Derrick Rose Had Stayed Healthy?

We all know the story of Derrick Rose—the youngest player to ever win MVP, who had the entire NBA fan base watching him in the late 2000s and early 2010s. The Chicago Bulls were back in the playoff conversation, maybe even title contenders, something we hadn’t heard since the Jordan era. And it was all thanks to Rose, who was quickly becoming a top-5 player in the league.

Coming off his MVP season, Rose was back at it, averaging 21.8 points, 7.9 assists, and shooting 47% from the floor. He was on track for another MVP campaign, and then bam, the ACL injury happened.

Just like that, what could have been a Hall-of-Fame career turned into one of the NBA’s biggest "what could’ve been" stories. Who knows how far the Bulls could’ve gone with a healthy, MVP-caliber Rose, especially when you remember they were on the verge of an NBA Finals appearance back in 2011.

Rose had the athleticism and playmaking ability to be one of the greatest point guards of all time. Had he stayed healthy, we might’ve witnessed one of the most electrifying careers in NBA history. Instead, Rose’s career became a rollercoaster, and we’re left wondering just how different things could’ve been.

What If Kobe Bryant Had Played for the Hornets?

Imagine a world where Kobe Bryant never wore the purple and gold. What if, instead of the Lakers, he stayed with the Charlotte Hornets after they drafted him in 1996? Would he still go on to become one of the greatest players of all time, or would his career have taken a completely different turn?

The Hornets weren’t exactly contenders at the time, but they were a solid, seasoned team with some talent—the kind of lineup that could’ve helped shape Bryant into the future scoring machine he became. With Muggsy Bogues at point guard, Glen Rice on the wing, and Vlade Divac in the post, Charlotte had the pieces to surround Bryant and develop his game.

Had Bryant stayed in Charlotte, the Hornets might’ve had a superstar to build around. But would they have given him the reins to do what he wanted, like the Lakers did? We’ll never know. 

 What If LeBron James Hadn’t Left Cleveland in 2010?

In 2010, LeBron James made one of the most controversial decisions in NBA history when he left Cleveland for Miami, “taking his talents to South Beach.” And trust me, “talents” was an understatement. James was coming off an MVP season, putting up 29.7 points, 8.6 assists, and 7.3 rebounds. Sure, the move got him his first two championships, but what if he had stayed in Cleveland? Could he have delivered a championship to Cleveland, and maybe even done it before 2016?

The Cleveland Cavaliers were competitive, and had James stayed put, Cleveland’s roster could’ve been improved with free-agent signings to help them compete with the top teams in the East. Instead, we got four years of a LeBron James-less Cleveland team, with the Cavaliers nosediving immediately after his exit.

What If the Lakers Had Kept Shaq?

What if the Los Angeles Lakers had been willing to meet Shaquille O'Neal’s financial demands? The duo of O'Neal and Kobe Bryant was already tearing the league apart. Sure, their personalities didn’t always mesh, but on the court, they were unbeatable. O'Neal’s dominance in the paint allowed Bryant to create for himself, making them one of the most dangerous matchups in league history.

In the 2003-04 season, Shaquille O'Neal was still performing at an elite level, averaging 21.5 points, 2.5 blocks, and 11.5 rebounds per game. And the Western Conference wasn’t getting any easier, but with a player like O'Neal anchoring the Lakers, they easily would’ve remained a top contender.  

But things don’t always work out, and the Lakers chose not to meet O'Neal’s financial demands. Had the Lakers been willing to write the check O'Neal deserved, maybe they could’ve added a few more rings to their collection. 

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