What If? 10 Moments That Could Have Rewritten Sports History

No matter what sport we’re talking about, there is a never-ending list of what-if moments that leaves us wondering about alternative outcomes. 

What if Scott Norwood makes the game-winning field goal in Super Bowl XXV? 

Would the 1994 Montreal Expos World Series history look completely different had the players decided against a strike? 

Here are the top-10 biggest what-if moments in sports history that could’ve dramatically changed the sports world’s landscape.

What Makes a Great Sports What-If?

The majority of the what-if moments ranked below share a common legacy theme that impacted championship outcomes. The outcomes and decisions from these events have realistic alternative scenarios that would’ve changed sports history. 

The 10 Biggest What-If Moments, Ranked

10. What If Tiger Woods Stayed Healthy? 

Woods’ name immediately gets mentioned in any PGA Tour G.O.A.T. conversations. He holds 50 PGA Tour records. Lately, the topic is whether or not Woods will ever be healthy enough to play again.

Woods hasn’t competed since 2024, when he played in just five PGA Tour events and missed the cut in three out of the four majors. Woods currently has 82 career wins, and that number would likely be much higher had his surgeries not derailed his legendary career.

9. Nordiques Trade Eric Lindros To The Flyers

Eric Lindros being selected No. 1 overall in the 1991 Entry Draft remains a forgettable moment for Quebec Nordiques fans due to the 18-year-old declining to put on the team jersey. Lindros demanded a trade and was sent to Philadelphia without playing a single game for the Nordiques. 

What if Lindros played for the Nordiques? While it may have created some short-term excitement, it probably wouldn’t be enough to help the NHL’s smallest market team (now known as the Colorado Avalanche) survive.

One interesting aspect of this particular what-if is that it might have worked out worse for the Avalanche if Lindros hadn't demanded a trade. The Aves used pieces acquired in the deal (primarily Peter Forsberg) to win two cups.

Lindros was a one-man wrecking crew for the Flyers but he never won a cup for the team. He came painfuly short in the 1997 Stanley Cup Finals, as the Flyers were ultimately swept by the Detroit Red Wings.

8. Gordon Hayward’s 2010 Halfcourt Shot Miss 

Looking back at the 2010 NCAA Men’s Basketball National Championship Game, it’s hard to forget how Butler’s Gordon Hayward nearly sent shockwaves through the college hoops universe. The No. 1 Duke Blue Devils had a 61-59 lead at Lucas Oil Stadium, which was only six miles from the Butler campus. 

There was just enough time remaining for Hayward to launch a desperation three from halfcourt. The shot ended up rattling around the rim and missing. Had he scored, besides an all-night celebration around Indianapolis, Butler basketball history would’ve permanently changed.  

7. New England’s Almost Perfect Season

The 2007 New England Patriots made NFL history by becoming the first team to go 16-0 during the regular season. However, it wasn’t a perfect one, as League MVP Tom Brady and company lost Super Bowl XLII to the New York Giants, 17-14.

New England was winning 14-10 with 2:42 remaining. It left plenty of time for the famous comeback drive.

David Tyree helmet catch from Eli Manning that set up the game-winning TD and spoiled the perfect season. If Tyree never makes the catch, the Patriots dynasty looks even stronger.

6.  USA Basketball Underperforms at the 2004 Summer Olympics

The 2004 USA Men’s Basketball roster was absolutely stacked with LeBron James, Tim Duncan, Allen Iverson, Dwyane Wade, and Carmelo Anthony. On paper, the Americans should’ve absolutely dominated, but they dropped their opening game to Puerto Rico and lost in the semifinals to Manu Ginobili and Argentina, 89-81. 

If this group spent more time building team chemistry leading up to the Games, they might’ve actually won gold instead of the bronze. 

5. 2004-05 NHL Lockout

The 2004-05 NHL season will forever be a what-if moment as it marked the first time a North American pro sports league had an entire season wiped out over a labor dispute. There was no Stanley Cup champion crowned. 

The two sides failed to come together over the salary cap. Imagine how many more records the human highlight reel Alex Ovechkin may have broken had the start to his NHL career not been delayed. 

4. 1994 Montreal Expos: What If There Was No Strike? 

Without a shadow of a doubt, the 1994 Montreal Expos were enjoying their best season in franchise history. The team had MLB’s best record (74-40) and was leading the National League East by six games. Unfortunately, the season will always be remembered with the words “what if” because of the players' strike. The entire postseason, including the World Series, was canceled. 

Besides never getting to see if they were good enough to win the World Series, the team relocated to Washington, D.C., a decade later. 

3. Babe Ruth Traded To The Yankees 

If somebody had told the Red Sox selling Babe Ruth to the Yankees would lead to an 86-year World Series championship drought, the transaction might’ve never happened. Ruth was the big reason why the Sox won three World Series titles between 1915 and 1918. Following the trade, Ruth helped New York win four WS crowns. 

Rival Boston, meanwhile, waited what seemed like a lifetime for the Curse of the Bambino to finally end. Unfortunately, there is no way of knowing how many more titles they would’ve won if Ruth stayed put.

2. Scott Norwood’s Missed Kick

Buffalo Bills fans avoid watching Super Bowl XXV replays due to Scott Norwood’s 47-yard field goal going wide right. It had the distance, but it was no good, and the New York Giants won, 20-19. We could make a case that the Bills are simply cursed when it comes to the Super Bowl, as this was the first of four straight Super Bowl appearances. The next three ended in double-digit losses. 

If Norwood makes the kick, maybe it ends up being the first chapter to the Bills' Super Bowl dynasty. 

1. Michael Jordan and the 1984 NBA Draft

The 1984 NBA Draft class is arguably the best of all time with future hall-of-famers Jordan, Charles Barkley, Hakeem Olajuwon, and John Stockton. It also included Bowie going No. 2 to Portland. That decision allowed the Bulls to select Jordan No. 3 and build a championship dynasty with six titles, three coming after Jordan’s short-lived retirement. 

Even though the 7-foot-1 Bowie played 10 years in the NBA, the word bust is often tied to his name due to significant injuries. Had Portland selected Jordan instead,  maybe the franchise wouldn’t be stuck in its current 49-year championship drought.

The One What-If That Could Have Changed Everything

Jordan is one of the first names that comes up when people are having an NBA G.O.A.T. debate. Had he gone to Portland instead of Bowie, the Trail Blazers, not the Bulls, would likely be the franchise listed among the greatest NBA dynasties. Had the alternative scenario happened, the current Chicago chatter might be about a never-ending championship drought that currently sits at 28 years.