Top 20 What If Scenarios in Sports History

“What if...” No two words in the English language spark the imagination as much as this. We’ve all had slews of such moments, wondering how our lives would be if we’d made a different decision for sch

“What if...” No two words in the English language spark the imagination as much as this. We’ve all had slews of such moments, wondering how our lives would be if we’d made a different decision for school, friendship or asking someone out on a date. History is packed with moments that make you wonder how vastly different this world would have been with a single bullet going another way, a key figure dying or surviving, a battle won or lost, any of which could have transformed the entire world.

In sports, such moments abound on a weekly basis and gain even more traction as years roll by. Countless times, a single play has made all the difference between champions and losers, goats and heroes, a season of success or one of tragedy. While it’s easy to go on just plays that could have gone another way, there are bigger questions around, ones that truly make you wonder how the sports world would be a different place right now. It’s not just certain games or trades, although those are included. There are bigger questions, ones that would have affected their organizations big time, the lives of so many players, coaches and teams and even fans and would have reshaped the sports world into something almost unrecognizable today. Here are the 20 biggest “What Ifs” in sports and makes you marvel at what could have been.

Continue scrolling to keep reading

Click the button below to start this article in quick view

Start Now

20 LeBron James goes to college


Everyone who saw him knew LeBron James was a star in the making and he knew it too. Thus, he decided to jump right from high school to the pros and thus became the focus of the 2003 NBA Draft en route to a wild championship career. However, if James had decided to go to college instead, it would have shifted things up a lot. Whatever school would be lucky enough to grab him might well have been a serious NCAA title contender and while there was the risk of him getting injured, James would also have been able to learn more of his skills and thus be far more seasoned and title-ready when he entered the NBA.

It also affects the draft of whatever year he became eligible. Had he decided to just do one year, than in 2004, the Orlando Magic could have nabbed him. Had it been 2006, the Bulls could have gotten him and thus he could more easily claim the title of “the next Jordan.” Had he stayed all the way through and been up in 2007, Portland or Seattle would have nabbed him. Thus, James’ entire NBA career would have been shifted which means he might never have gone to Miami, robbing them of a major trio and two championships.

College might well have helped James out in being more prepared for the NBA and the delay of even just one year would have meant a major boost to a different team than Cleveland.

19 The Cowboys don’t trade Herschel Walker


In 1989, the Dallas Cowboys stunned everyone by trading star running back Herschel Walker to the Minnesota Vikings in a massive deal that involved various draft picks from both teams and players that included Alex Stewart. At the time, the Dallas media were harsh, calling this a bad move. It turned out they were right, it was a bad move…for the Vikings. Walker never lived up to expectations there and faltered badly. Meanwhile, Jimmy Johnson would cunningly use the draft picks to get his hands on Emmett Smith, Darren Woodson and others who would forge the backbone of the Cowboys team that would win three Super Bowls in four seasons.

Keeping Walker would have changed all of that as Dallas would have lost out on Smith and others, a good team but not quite the same, maybe getting one Super Bowl but not the dynasty. That would have changed the face of the NFL of the early ‘90s, especially with whoever would nab Smith (perhaps the Vikings) and other teams like the Eagles and perhaps the 49ers would have become more dominant. Walker’s career might still have been so-so but at least he wouldn’t be a walking punchline for every bad trade decision in NFL history since.

18 Tyson beats Douglas


When Mike Tyson fought James “Buster” Douglas in January of 1990, he was such an unstoppable force that most gamblers didn’t even bother putting the bout on their betting lines. However, Douglas pulled off one of the greatest upsets in history by knocking out Tyson to win the heavyweight championship. It’s clear Tyson was never the same after that, sending him into his professional and personal tailspin that transformed him from “the baddest man on the planet” to a joke.

Had he crushed Douglas as expected, Tyson’s standing as a respected champion would have remained strong, he’d have easily gotten more title bouts going and boxing wouldn’t have suffered its own fall in mainstream attention. Tyson himself would have avoided some of the personal falls (maybe even his jail time) and still be regarded as truly one of the greatest ever, perhaps retiring as champion with a record few could touch.

17 The Reds keep Frank Robinson

Rhodes/Klumpe Reds Hall of Fame Museum Collection

In 1965, after a decade of loyal service and over 320 home runs, Frank Robinson was traded from the Cincinnati Reds to the Baltimore Orioles with word that Reds management considered him “an old 30.” Robinson wasted no time making them regret that decision as in his very first year with his new team he won the Triple Crown, was named MVP (still the only man to win that honor in both leagues) and pushed Baltimore to their first World championship. He would go on to help the Orioles win three more pennants, another World Series (over, ironically, the Reds) and become the first black manager in the majors.

Robinson could have helped Cincinnati become “the Big Red Machine” a few years earlier, winning the World Series before 1975, which would have cut into the Oakland A’s dynasty. That means Reggie Jackson wouldn’t have risen so far as to be worth so much for the Yankees which could have changed things later in the decade. While the Reds weren’t exactly cursed, keeping the amazing slugger Robinson would become could have helped Cincinnati dominate the 1970s far more.

16 Michael Jordan doesn’t retire in 1993


When Michael Jordan first retired in 1993, it seemed the perfect capper to a great career with three straight NBA championships but still seemed short at only nine years. His baseball tenure was forgettable to say the least and thus no one was surprised when Jordan returned to the Bulls and led them to a second three-peat.

Had he not retired at all, it’s easy to see Chicago dominating straight on in ’94 and ’95 which means the Houston Rockets could have kissed those titles goodbye and the Bulls could have challenged the Celtics’ record for consecutive championships. On the other hand, the franchise might have gotten stagnant, not made moves (like the signing of Dennis Rodman) that helped the second threepeat take place and thus not getting those last few titles, which would have meant better luck for the Jazz. Either way, it would have kept Jordan’s legacy a bit better without that break, maintaining his greatness straight on and still retiring on top and maybe even filling both hands with rings in the process.

15 Drew Blesdoe isn’t injured


For all his great achievements as a player, most consider Drew Blesdoe’s greatest contribution to football being getting injured in the second game of the 2001 season, putting him out for the year. Thus, Tom Brady would take over as the main QB for the New England Patriots and lead them to the AFC Championship. While Blesdoe did great in that game when Brady was hobbling, it was Brady who got the win in the Super Bowl and basically paved the way for the Patriots dynasty.

One has to wonder what might have been in Blesdoe didn’t go down and Brady didn’t get to show his stuff. While good, Blesdoe just wasn’t in that same league and thus doubtful he’d have led the Patriots to the Super Bowl and thus the dynasty we know today doesn’t come to be. As a result, we likely get a Raiders/Rams Super Bowl that season.

It’s possible Brady might have been traded before the Patriots realized what they had and thus charge another team to a massive championship reign. The NFL landscape today would be a lot different without the powerhouse of the Patriots and Brady pushing another team to great heights.

14 The Black Sox don’t exist


In 1920, the world was stunned by the revelation that eight members of the Chicago White Sox had colluded with gamblers to throw the 1919 World Series to the Cincinnati Reds. All eight, including star “Shoeless” Joe Jackson were banned for life and the White Sox would take 85 years to win another World Series. Had these men decided to put their own pride and the games ahead of cash, the baseball world would have been different.

A quite strong team, the White Sox could have easily won that World Series and more (they were in the hunt for the pennant in ’20 before the scandal erupted) and that would have cut into the rise of other teams like the Yankees. More importantly, Jackson would have continued his amazing work as one of the best players in the history of the game and be enshrined in the Hall of Fame as he deserves. It would have saved the baseball world a lot of headache and heartache and quite possibly changed the landscape of the 1920s and beyond in who was the baseball powerhouse of the time.

13 Len Bias lives


Few stories in sports history are as tragic as Len Bias. A stellar college athlete, he was considered by just about every basketball expert of the time to be one of the best players alive. He was picked in the NBA draft by the Boston Celtics, the defending NBA champions of the time was all smiles talking of how he was ready to play for them. Less than 24 hours later, he was found dead of a drug overdose at the age of 22. His death was shocking, really helping change the idea of “casual” drug use at the time and we’re left with what might have been.

The Celtics were already great but with Bias, they would have really taken off, staving off the championships of the Lakers and Pistons. It’s easy to imagine Bias and Michael Jordan becoming great rivals on the court and Bias could have given MJ a run for the money as the best in the league. The long drought between NBA titles in Boston wouldn’t have happened as we’d have enjoyed many good years and his inevitable Hall of Fame entry. It just makes you sadder to realize what could have been and the terrible loss he made on the NBA world.

12 The Cubs keep Lou Brock


One of the most notable moments of the decades-long “curse” on the Chicago Cubs was in 1964 as the team traded Lou Brock to the St. Louis Cardinals for pitcher Ernie Broglio. To call it a bad move is an understatement as Brock would turn into one of the game’s greats, setting the record for bases stolen and lead the Cardinals to three pennants and two World Series championships. Had the Cubs kept Brock, it would have helped them immensely with an otherwise strong team that was just missing that key ingredient to take off.

The most immediate effect is that it would have been the Reds, not the Cardinals, who took advantage of the Phillies’ infamous collapse to win the 1964 pennant and perhaps the World Series. Also, the “El Birdos” of ’67 and ’68 wouldn’t be either while Brock would be able to help Ernie Banks and the rest of the Cubs out majorly, especially in 1969 to win the pennant instead of the “Miracle Mets.” Ask any Cubs fan and they’ll agree. If Brock had stayed, we wouldn’t be talking about any “curse” on the Cubs today.

11 Gretzky isn’t traded


In 1988, the NHL suffered a seismic shift when the Oilers traded Wayne Gretzky to the Los Angeles Kings. It was a shocking moment that basically ended the Oilers dynasty and elevated the Kings up majorly. Had the trade not happened, the NHL might have a lower profile without more mainstream attention, a profile that would have hurt it badly with such things as the 2004 lockout and other events. L.A. would have sunk badly without Gretzky and possibly not as big a push for hockey in cities like Tampa Bay or Phoenix. Of course, the immediate impact would have been Edmonton would have gotten another Cup or two and, more importantly, Gretzky would have ended his career there, not giving the NHL the major kick it may have needed in the 1990s. The Oilers could have possibly matched or surpassed the Habs record of five consecutive Stanley Cups.

10 The 1994 MLB strike doesn’t happen


In 1994, MLB was doing pretty well with the Montreal Expos and the Chicago White Sox having great seasons, several players (Matt Williams, Barry Bonds, Ken Griffey Jr and Frank Thomas) challenging the single-season home run record and fan interest high. All that ended when the players and owners’ bitter dispute over the distribution of money ended in a strike. Despite the hopes of so many, no solution could be found and thus for the first time, there was no World Series.

Had the strike been averted, the home run record might well have fallen to one of those men and it would have also helped the long-term numbers of several players and their careers. For the question of who would win the World Series that year, both Sox and Expos players insist it would have been them and had it been the latter, the Expos might still be around today. There’s also the possibility that, without needing to do anything to get fans back, the MLB might have come down harder on performance-enhancing drugs which would have affected things like the 1998 home run race. If nothing else, it would have avoided a massive black eye for the entire sports world and helped quite a few careers as well.

9 UFC never takes off

Mark J. Rebilas-USA TODAY Sports

It’s often forgotten the major uphill struggle MMA had to acceptance, from people slamming it as “blood sport” to moves to have it banned from states. It did forge ahead under the UFC banner to achieve the mainstream success we know now but it’s intriguing to think of how things would be without the UFC able to truly get going. The sport might still be around but far less mainstream, more an “underground” feel to it and thus we’d be lacking the major stars we know today like Ronda Rousey.

The PPV market would suffer a bit more without the reliability of the UFC to rest on and it wouldn’t have had the influence on other sports and even pro wrestling. MMA itself might have survived but never to such great heights of respectability and fame and thus the fighting world would have been affected big time along with the careers of so many MMA stars.

8 Steinbrenner buys the Indians


Love him or hate him (Lord knows, there’s enough people on both sides), George Steinbrenner is one of the most famous figures for the New York Yankees, overseeing their rise, fall and rise again to grand success and a dominant force in baseball. It’s easily forgotten that it’s only because Steinbrenner couldn’t buy his first choice, his hometown Cleveland Indians. But if he had, things would have been far, far different.

With Steinbrenner’s money, the Indians would obviously have been able to snag some major players and push them hard, easily becoming pennant contenders and perhaps World Series champions. Obviously, we would still have the issues of Steinbrenner’s temper and the revolving door of managers but maybe Steinbrenner would have played differently with the Cleveland media than with the more hostile New York.

Meanwhile, without Steinbrenner, the Yankees would have taken a lot longer to rise out of their funk from the late 1960s onward, perhaps falling to a second-rate team in their own city and while still contenders, not as many of their late trophies. While it’s hard to imagine King George not in New York, Indians fans might well put up with him if it meant a lot more trophies in Cleveland.

7 The Trail Blazers draft Jordan


After 30 years, it still sticks in the craw of Portland fans that they could have had the greatest basketball player of all time. While Houston had the first pick in the 1984 draft and could have drafted MJ, they grabbed Hakeem Olajuwon, so they were just fine.With the second pick, the Trail Blazers passed on Jordan for Sam Bowie, a good but not spectacular player prone to injury. Thus, the Chicago Bulls were able to grab Jordan and launch a decade and a half of success. Had Portland gotten him instead, it’s doubtful they would have ended up being so utterly successful (it took a while and Phil Jackson to get Jordan a championship) but with a duo of Jordan and Clyde Drexler, Portland would have nabbed some titles in the early 90s.

The Bulls would have suffered, of course, never the big team they became without the fancy United Center which means the Pistons own dynasty might have gone longer. Jordan would still have been Jordan but probably a few less rings in Portland although they would have been pushed a lot more thanks to his presence rather than losing the chance of a lifetime.

6 Free Agency never happens


When Curt Flood’s challenge created the arbitration that did away with the reserve clause, it transformed sports forever. No longer were players bound to a team no matter what with little say aside from arguments over exact pay but the owners keeping all the power. On the one hand, the benefits are obvious as without free agency, owners would still dominate with crappy wages for great players and consolidating power so much. On the other hand, it’s also led to the outrageous salaries of today and it can be argued players performed a lot better when they had to fight for their jobs and not just rest knowing they were getting millions no matter what.

It also would have meant avoiding the conditions that caused the damaging baseball strikes of 1981 and 1994 and other incidents in other sports. Either way, if free agency didn’t occur, the sports world would look a lot different, both good and bad, and makes you realize just how much Flood’s challenge shifted things up.

5 The Bulls get Magic Johnson


The idea of Johnson in anything but a Lakers uniform seems hard to fathom. But it was literally the flip of a coin that allowed Los Angeles to get the chance to draft the star college player instead of the Chicago Bulls. Had that flip gone the other way, Magic would have begun in Chicago and while he would have lacked the aid of Kareem or Pat Riley, the idea of a Magic-led team never winning a championship is impossible. The Lakers would have been good contenders but never “Showtime” while Johnson would have helped the Bulls to great success and maybe even turning Chicago into a dynasty a decade earlier.

Of course, with Magic helping them to winning seasons, the Bulls would never have gotten the chance to draft Michael Jordan. Then again, if, by some quirk of fate, it still happened, a team with Magic AND Michael would have been quite possibly the most dominant force the NBA has ever seen.

4 The Red Sox keep Babe Ruth


It’s the sale that instigated what Boston fans called an 86-year old curse. Needing money, Red Sox owner Harry Frazee sold Babe Ruth to the Yankees for $125,000. This was after Ruth had set a record for home runs as well as a top-notch pitcher and helping the Red Sox to winning the World Series in 1916 and ’18. While Boston fans of the time were upset, no one dreamed this would be the most significant trade in baseball history. It wasn’t just Ruth but other big players that would form the heart of the Yankees “Murderers Row” that basically turned the second-rate team into a dynasty.

Without Ruth, it’s impossible to see that happening. New York might have gotten a championship or two but it was the Yankees’ mystique that Ruth helped create that made them the must-play team for many aspiring players like Joe DiMaggio or Mickey Mantle. Without that, the Yankees would never had been the legendary team that dominated the World Series in the late 1930s, ‘40s and ‘50s which means the title would have been far more spread out across the Majors. Not to mention, Boston would have avoided so many years of heartbreak and boast far greater success while the Yankees would be only a so-so team and so many careers would have been affected by the loss of baseball’s greatest dynasty.

3 The Giants and the Dodgers stay in New York


Baseball was always going to migrate to the West Coast, that was obvious. However, if the New York Giants and Brooklyn Dodgers had ended up staying, it would have been a seismic shift to the entire baseball world. Instead of inheriting existing teams, Los Angeles and San Francisco would have needed to start expansion clubs from scratch and thus it would have taken a long while for either city to reap the benefits of a championship.

Brooklyn fans might have gotten the new stadium they wanted as they continued their winning ways along with the Giants. This would have meant bad news for the Yankees who suffered a massive collapse in quality and fan attendance in the late 1960s; indeed, with two other teams in the region taking away fan heat and money, the Yankees might very well have been sold and even moved out of New York (which may sound crazy but then so was the idea of the Dodgers and Giants leaving).

There’s also the fact that there would have been no need for the creation of the Mets which would have affected the careers of hundreds of players and numerous pennant chases and World Series championships. Had the concessions been made to keep both teams in the Big Apple, the baseball landscape today would be a far different field.

2 The AFL never forms


The creation of the American Football League was a massive shift for pro football that was greatly needed. The AFL introduced a flashier way of playing, more into high passing and running than the old-fashioned hard-knocks and the need to compete with that forced the NFL to step up its own game to take them on. Without the AFL, football today would be a lot less flashy and slower which may not be as great to watch. The AFL also meant expansion to secondary markets and while the NFL might have expanded, it’s doubtful places like Jacksonville, Phoenix, Tampa Bay and Buffalo would have earned their own teams.

The rise of the rivalry between these two leagues led to massive interest and without that, it’s doubtful football would have overcome baseball as the most popular sport in America. The biggest issue is that it was the AFL-NFL clashes that created what we know as the Super Bowl. While we would have an NFL Championship, it wouldn’t be the massive media blitz and internationally watched event it is today. The truth is that without the AFL, the NFL as we know it today wouldn’t exist.

1 The Majors are never segregated


When Jackie Robinson made his debut for Brooklyn in 1947, he was met with harsh criticism but was seen as a man finally breaking the color barrier. His great success would pave the way for more blacks in the major leagues and showcasing their incredible talent and how much they belonged. It makes you wonder how differently the Major Leagues would have been if they had never set up this system in the first place and allowed black players to be in from the start. You can imagine the records to be set by Gibson or Satchel Paige, how they would push aside players like Ruth and Cobb, the question of how the lives and records held for so long by white players would have even been achieved with blacks playing against and alongside them.

You can imagine the effect across the fanbase as many saw the coming of Robinson as a dramatic shift in American racial feelings and this could very well have led the Civil Rights movement decades earlier. To imagine all the ways various championships would have been shifted thanks to the presence of black players is fascinating and the Hall of Fame would look a lot different as well. It would have the effect that Robinson, while remembered as a good player, wouldn’t be the heroic icon he’s known as today. But then again, Robinson himself might be the first to accept that if it meant seeing more of his race already accepted into the majors and showing how baseball is meant for all.

Give TheSportster a Thumbs up!

Looking for an AD FREE EXPERIENCE on TheSportster?

Get Your Free Access Now!

More in Entertainment

Top 20 What If Scenarios in Sports History