Some players don’t just play the game — they tilt it in their favor. These stars always came out on top when it mattered most, whether with clutch hits, big-game moments, or a relentless competitive fire.
This list concerns the winners, from dynastic legends to quietly dominant grinders. Not necessarily the flashiest or loudest, just the guys who got it done again and again, often when the stakes were highest.
20. Madison Bumgarner

If there were a postseason mountain to climb, Bumgarner would already be at the top waiting. He made October look like a casual bullpen session.
19. Jorge Posada

Posada never needed to be the loudest voice in the room. He was quietly essential to the Yankees’ winning machine. He just kept catching, hitting, and helping them win.
18. Paul Molitor

Molitor made every team better and seemed to have winning in his DNA. Whether it was Milwaukee or Toronto, the guy just arrived and delivered.
17. Justin Turner

Turner became the heart and soul of a perennial Dodgers contender. His playoff bat was always hot when the moment called for it.
16. Orlando “El Duque” Hernández

The guy pitched like he was born for October. No matter the pressure, El Duque delivered wins when the Yankees needed them most.
15. Miguel Tejada

Tejada was a glue guy with pop who helped carry Oakland through its Moneyball years. He wasn’t just stats — he was spark.
14. Jon Lester

Big-game pitcher with ice in his veins, Lester brought championships to both Boston and Chicago. Not many can say that.
13. Kenny Lofton

Everywhere he went, winning seemed to follow. Lofton brought elite speed, defense, and postseason energy to many playoff teams.
12. Jorge Soler

Soler turned into a postseason monster seemingly out of nowhere. When he got hot, he was the X-factor in championship runs.
11. Yadier Molina

Molina wasn’t just a catcher — he was the Cardinals’ on-field GPS. If winning is a habit, he had it in spades.
10. David Justice

Justice came up big in huge moments and always seemed to be on the contending teams. He was the clutch bat that contenders coveted.
9. Manny Ramirez

Manny being Manny meant also being a ridiculous playoff performer. When the spotlight got bright, his bat got even louder.
8. Derek Jeter

Jeter lived for the moment and made winning look effortless. You just expected him to pull something off in crunch time.
7. Albert Pujols

Pujols mashed during the regular season and stepped up when the lights got bright. His early Cardinals years were a masterclass in championship-level baseball.
6. Andy Pettitte

You needed a postseason win? You called Pettitte. He made October look like a second home.
5. Buster Posey

Posey was the calm in the storm for the Giants’ three-title run. A leader behind the plate and a bat you trusted in any moment.
4. Alex Bregman

Say what you want, but Bregman shows up when it matters. He’s been a key cog in Houston’s never-ending playoff runs.
3. Reggie Jackson

They didn’t call him Mr. October for nothing. Reggie hit when it counted and made sure everyone knew it.
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2. Mariano Rivera

The ultimate closer who locked down more playoff games than some teams even reached. If he entered the game, you already started writing the W.
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1. David Ortiz

Ortiz didn’t just win games — he dragged teams to victory. If clutch had a face, it would be Big Papi in October.
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