Best Sports What-Ifs of All Time

Key Insights

• Len Bias dying two days after the Celtics drafted him in 1986 is the most consequential single what-if in NBA history, because the alternate universe where he plays eight years alongside Larry Bird produces a Boston dynasty that never needed to end
• Tom Brady going 199th in the 2000 draft is the most discussed what-if in NFL history, because every team that passed on him before Chicago picked him had an opportunity to change their franchise trajectory permanently
• Sam Bowie over Michael Jordan in 1984 is the cleanest draft what-if in any sport, because the outcomes are so clearly opposite and so well documented

The Injury What-Ifs

The hardest category to process because the alternate history requires no one making a different decision. It just requires someone staying healthy.

Len Bias and the Boston Celtics

ParisBasketball ranks Len Bias as the number one NBA what-if, and the case is straightforward and devastating.

Len Bias was taken second overall by the Boston Celtics in the 1986 draft, two days after the Celtics had won a championship with Larry Bird at the peak of his powers. He died of a cocaine overdose two days after being drafted. The Celtics won one more title in 1986 and then began the slow decline that ended the Bird era.

The alternate history in which Bias plays his prime years alongside Bird, Kevin McHale, and Robert Parish produces a dynasty that could plausibly have extended the Celtics' championship window by five to seven years. That's the what-if: not just a player's career, but an entire era of Boston basketball that existed in the draft room for two days.

Derrick Rose's Knees

The youngest MVP in NBA history in 2011, at 22 years old, before multiple knee injuries converted a Hall-of-Fame trajectory into a career of occasional glimpses of the player he was supposed to be:

• The 2010-11 Rose was legitimately special in a way that suggested a decade of MVP contention
• The injuries didn't just shorten his peak but changed the character of his game permanently
• The Chicago Bulls' alternate history with a healthy Rose includes multiple Finals appearances and at least one plausible championship window

Grant Hill's Ankles

An All-NBA level player in his prime whose recurring ankle injuries turned what should have been a twenty-year peak career into something significantly shorter and more fragmented:

• Hill's Detroit peak was genuine enough to produce six All-Star selections in his first six seasons
• The Orlando ankle problems changed the trajectory so completely that his post-injury career feels like a different athlete
• The what-if requires only that the ankle holds up, which makes it one of the most straightforward alternate histories in the sport

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The Draft What-Ifs

The cleanest category because the alternate history is clearly defined: one team makes a different pick and both franchises change permanently.

Sam Bowie over Michael Jordan (1984)

The classic draft what-if, and the one that Bleacher Report revisits as the most discussed selection error in sports history.

Portland took Bowie at number two while Jordan fell to Chicago at number three. The specific clarity of this what-if is what makes it the standard for draft regret: Jordan became the greatest basketball player of all time, Bowie's career was significantly limited by injury, and the Portland Blazers spent years wondering what could have been. The Houston Rockets also passed on Jordan at number one, choosing Hakeem Olajuwon, who won two championships, which is the one version of the what-if that has a legitimate counterargument.

Greg Oden over Kevin Durant (2007)

The most painful modern draft what-if, and the one with the cleanest contrast between outcomes:

• Oden's chronic knee injuries limited him to 105 career games
• Durant became one of the most prolific scorers in NBA history and won two championships
• Portland's alternate history with a healthy Durant includes multiple title windows during the prime years the Blazers spent managing Oden's health

Tom Brady at 199th (2000)

Every team in the NFL passed on Tom Brady six times before the New England Patriots took him in the sixth round. He became a seven-time Super Bowl champion and the most decorated quarterback in NFL history:

• The 198 picks that came before Brady represent 198 franchise decisions that could have permanently altered NFL history
• The specific teams that passed most recently before New England, including multiple playoff-caliber rosters, had the clearest opportunity
• The what-if isn't just about Brady's career but about which franchise would have built a dynasty around him if New England hadn't

The Game and Legacy What-Ifs

Mike Tyson Never Loses to Buster Douglas

Bleacher Report's what-if list specifically notes how much of Tyson's mystique evaporated in Tokyo in 1990. Without the Douglas loss, Tyson's aura remains intact, his career timeline looks different, and the specific psychological damage that the upset produced never happens:

• The unbeatable Tyson persona was the foundation of his cultural impact
• The Douglas fight didn't just end the streak but revealed a Tyson who had stopped preparing properly
• The alternate history requires asking whether the Tyson who lost in Tokyo was ever the same fighter as the one who preceded him

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The best sports what-ifs are the ones where the alternate history is clear enough to be specific but can never be proven, which keeps the conversation permanently open. Bias doesn't die. Rose stays healthy. Portland takes Jordan. Brady goes earlier. Each one produces an alternate sports history that's more interesting than most sports fiction, because the gap between what happened and what could have happened is real.

FAQ

What is the greatest sports what-if of all time?

Len Bias' death is the most consequential single moment. Tom Brady falling to 199th is the most discussed. Sam Bowie over Jordan is the clearest contrast in outcomes. All three are correct depending on the sport and the criteria.

Could any team have won with Sam Bowie as well as Chicago won with Jordan?

The Houston Rockets, who took Olajuwon at number one, won two championships without Jordan. That's the clearest argument that Jordan specifically wasn't necessary for every team to succeed. Portland's specific roster and coaching situation is the more relevant what-if.

Did any team pass on Tom Brady regret it publicly?

Several NFL front-office figures have addressed the Brady miss over the years. The New England Patriots themselves have acknowledged the specific fortune involved in taking him where they did. Most organizations that passed have been less forthcoming.

What would the Celtics dynasty have looked like with Len Bias?

The most common projection involves three to five additional championship windows through the late 1980s and early 1990s, with Bias and Bird complementing each other in a way that would have made Boston the dominant team in the NBA through the Jordan era's early years.

Are injury what-ifs less interesting than draft what-ifs?

No, and the Bias case specifically is considered more significant than most draft what-ifs because the circumstances are so extreme. A draft mistake involves a decision that could have gone differently. An injury what-if involves circumstances entirely outside anyone's control, which makes the alternate history feel more genuinely accidental.

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