Baseball history is full of legends who reached their full potential, but what about those who didn’t? Whether due to injuries, bad luck, or just bizarre circumstances, these players left us wondering what could have been.
Here are the 15 biggest “what if” careers in MLB history, ranked from “man, that sucks” to “baseball gods, explain yourselves.”
15. Grady Sizemore
Remember when Grady Sizemore was the future of baseball? The three-time All-Star was a five-tool stud with the Cleveland Guardians (then Indians), but injuries robbed him of what should have been a Hall of Fame-caliber career.
14. Kerry Wood
Striking out 20 batters in your fifth career start should set you up for a legendary career. Instead, injuries derailed Kerry Wood’s chances of becoming one of the all-time greats. He was still good, just not what he could have been good.
13. J.R. Richard
A 6’8” flamethrower who struck fear into hitters, J.R. Richard looked like a future Hall of Famer before a stroke ended his career at 30. He should have been an all-time great, but fate had other plans.
12. Brandon Webb
A Cy Young winner and one of the nastiest sinkerballers of his era, Webb’s career went off the rails fast due to injuries. From elite ace to completely out of the league in just a few years—tough break.
11. Mark Prior
Few pitching prospects were as hyped as Mark Prior, and for a brief moment, he lived up to it. Then, as Cubs fans know all too well, injuries turned him from a potential Hall of Famer into a baseball “what if.”
10. Tony Conigliaro
A 22-year-old with 100 career home runs, Tony C. was cruising toward superstardom before a devastating beanball derailed his career. He made a brief comeback, but we’ll always wonder how far he could have gone.
9. Bo Jackson
Bo knew baseball. He also knew football. And if not for a devastating hip injury, he might have been an all-time great in both sports. Instead, we’re left with highlight reels and dreams of what might have been.
8. José Fernández
Fernández was on his way to superstardom before his tragic passing at just 24 years old. He had Cy Young potential, electric stuff, and an infectious love for the game. A heartbreaking “what if.”
7. Dwight Gooden
Doc Gooden dominated baseball at 19 and looked destined for Cooperstown. Unfortunately, off-field struggles and substance abuse derailed what could have been an even greater career.
6. Thurman Munson
Munson was the heart and soul of the Yankees and a legit Hall of Fame-caliber catcher before his tragic death in a plane crash at just 32. Who knows how many more championships he could have led them to?
5. Herb Score
A young lefty who was on track to become one of the best pitchers of his generation, Score’s career took a brutal turn when he was hit in the face by a line drive. He never fully regained his dominance.
4. Don Mattingly
For a stretch in the ‘80s, Don Mattingly was the guy. Then, back problems sapped his power and cut short what could have been a legendary career. Yankees fans still wonder “what if.”
3. Ken Griffey Jr. (if he had stayed healthy)
Yes, The Kid is a Hall of Famer and one of the greatest to ever play. But imagine if he hadn’t lost so many prime years to injuries. He might have broken every record in the book.
2. Sandy Koufax (if he had a longer career)
Koufax is already one of the greatest pitchers ever, but what if he hadn’t retired at 30 due to arthritis? He was just that good—five more years and he might be the GOAT.
Related: Ranking The 15 Best Catchers In MLB History
1. Roberto Clemente
Clemente was already an all-time great before his tragic death in a plane crash at 38. Given how good he still was, it’s gut-wrenching to think of how much more he could have accomplished on the field.
Related: The 20 Most Beloved MLB Players in History
