Last Updated: October 23rd, 2026 by Matthew Brown
There is no question that whoever wins the World Series championship has won that particular season. As we all know in sports, earning a championship isn't about being the best team at the start of the season, but about being the team that has withstood the ups and downs to play the best at the end of the season.
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That being said, with all due respect to the teams on this list, some champions have had it easier than others. We're here to investigate the 10 most significant teams that fit this bill.
10. The 2017 Houston Astros: Baseball’s Most High-Tech Heist
Some teams create their own luck. The Houston Astros are probably the most infamous champions in baseball history, and that's saying something. For all of my non-baseball friends, I had to explain to them that it wasn't the sign-stealing that was the problem.
It was the technology that was used to do it.
Banging on trash cans has become synonymous with the franchise, and it's almost expected to still hear boos from fans whenever a player who was on that specific team comes to the plate.
9. 1985 Kansas City Royals: The Denkinger Call That Changed Everything
Jorge Orta is a name that will forever live in the hearts and minds of Cardinals and Royals fans for different reasons. This is one of the moments that happened on the biggest stage that is evidence in favor of replay review.
Managers and players today are spoiled to have the use of challenges that I'm sure the Cardinals wished they had in 1985.
8. 1996 Yankees: Jeffrey Maier’s “Helping Hand” to Glory
I think there is also a case to be made about the use of challenges in today's game that could still lead to unfortunate calls. I know the Yankees benefitted from the fact that there wasn't a challenge review system in place at the time, but with the way that some decisions are made these days, I think there's a chance that the officials at the replay headquarters could have gotten this call wrong too.
7. 1960 Pirates: Outscored by 28 Runs…Still Won?
One of the most improbable champions in history, the Pittsburgh Pirates of 1960 are fondly remembered by the city to this day. Even though other championships were won less than 20 years later, this particular one holds a special place in the hearts of Pittsburgh fans.
They know how much of an underdog they were, and they know how magical that Bill Mazeroski home run was, but all that does is make them even more proud of a team that never gave up and stood up to the goliaths that were the Yankees.
6. 1988 Dodgers: From Scioscia’s Shocker to Gibson’s Gimpy Miracle
The Oakland A's were looked at as a juggernaut in baseball. Even though this particular roster hadn't won a World Series championship, everyone in baseball thought they were destined to win it in 1988.
That was before the Dodgers came into the fold. Like Vin Scully said while Kirk Gibson hobbled around the bases, "in a year that has been so improbable, the impossible has happened."
5. 1987 Twins: The Metrodome’s Air-Conditioned Victory
This one is very dependent on how you view indoor stadiums. To this day, I have heard opinions that are both in favor of and against domed stadiums.
For the notorious Metrodome, I think there is some bit of argument that can be made that the Twins had a major home-field advantage. Either way, they played well enough at home to win the World Series, and that's a fact.
4. 2006 Cardinals: The Worst Record Ever for a World Series Winner
Like we said at the top, the team that plays the best at the end of the season will win the Commissioner's Trophy. The St. Louis Cardinals certainly did that in 2006. They snuck into the playoffs with 83 wins and got hot at the right time.
I'm sure some of you who remember the days before the Wild Card will say they didn't even deserve to be there in the first place. I can't deny that that's a fair point.
3. 1990 Reds: A Wire-to-Wire Fluke?
This championship team has always been a curious one. There were some stars and a Hall of Famer in Barry Larkin, but nothing that really pointed to them being able to take down the mighty Oakland A's.
Some will say that the A's lost that series more than the Reds won it, but I'd say it's hard to make that argument when the Reds earned a series sweep over the A's. Their domination has to deserve at least some credit.
2. 2000 Yankees: Dynasty’s Weakest Link
I think there will always be envy towards those dynastic Yankees of the late-90s and 2000s. However, it's that latter year that some critics point to as one where their opponents should have given them more of a fight.
For as fun as it was seeing the Subway Series on the grandest stage, this was also an opportunity to down a weakened dynasty that only went 3-15 in the games leading up to the playoffs.
1. 2011 Cardinals: Did the Rangers Actually Beat Themselves?
This series has always been looked at as epic. Now, if you're a fan of one team or the other, it can be seen as an epic comeback or an epic collapse. The Texas Rangers were on the brink of winning it all, but clutch moments just kept happening in favor of the Cardinals as they turned the series on its head and eventually won the title from the clutches of their opponents.
