Pitching greatness doesn’t always translate to champagne showers in October. Some of the most dominant arms in baseball history walked away with empty fingers when it came to World Series rings, despite having resumes packed with strikeouts, Cy Youngs, and jaw-dropping postseason performances.
Whether it was bad timing, bad luck, or just plain bad teams, these guys deserved a little more glory on baseball’s biggest stage. Here are pitchers who we all wish had just a few more World Series wins to their name.
12. Kevin Brown
Kevin Brown was a certified ace who could absolutely shove when it mattered. Unfortunately, his postseason career is remembered more for missed chances than championship rings.
11. Johan Santana
One of the best lefties of his era, Johan Santana never even got to pitch in a World Series. His brilliance deserved a bigger October spotlight—and maybe a ring or two to go with it.
10. David Price
Yes, he finally got one with the Red Sox, but his early years were full of postseason struggles and near-misses. Given how dominant he was in his prime, one ring feels a bit light.
9. Roy Halladay
Doc was a postseason magician—remember that no-hitter? But his playoff career started late, and the championship hardware never came. He deserved a moment on the mountaintop.
8. Clayton Kershaw
He’s got one ring now, but you’d be hard-pressed to find a more dominant regular-season pitcher with such a rocky October track record. One more World Series title would silence a lot of doubters.
7. Greg Maddux
Four straight Cy Youngs, a pitching savant, and yet only one ring with all those loaded Braves teams. It still feels like a crime that Atlanta didn’t win more with him at the front of the rotation.
6. Felix Hernandez
King Félix was stuck on some brutally bad Mariners teams. He was royalty without a kingdom—never even reaching the playoffs, let alone sniffing a ring.
5. Nolan Ryan
He has one ring from early in his career with the Mets, but let’s be honest—it wasn’t really his team. With all those strikeouts and all that fire, Ryan should’ve been spraying champagne a few more times.
4. Max Scherzer
Mad Max has picked up a couple rings, but he’s been so dominant for so long, it feels like he should have five. He’s the kind of pitcher who seems like he should be the last guy on the mound every October.
3. Pedro Martinez
Pedro finally got a ring with the 2004 Red Sox, but that barely scratches the surface of how good he was. If baseball were fair, he’d have a whole display case of championship hardware.
Read More: 15 Coolest MLB Stars of All Time
2. Tom Seaver
Seaver did win one with the 1969 Miracle Mets, but his career deserved a more traditional run of postseason dominance. The guy was the definition of an ace, and one ring just doesn’t do him justice.
Read More: The 15 Biggest Playoff Chokers in MLB History
1. Randy Johnson
He got his World Series moment with the D-backs in 2001 and absolutely earned it, but The Big Unit was so overpowering, it feels like he should’ve had a few more parade rides. One of the most intimidating pitchers ever, and still somehow under-celebrated when it comes to rings.
Read More: Ranking the All-Time Kings of Clutch in MLB
