Last Updated: August 14th, 2026 by Michael Schatz
You know the phrase "there's always next year"? That can get pretty tiring when it happens year after year after year. A lot of times, a franchise's failure comes from the top down. We want to go over some of the most notorious examples of MLB mismanagement.
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10. Seattle Mariners: The Playoff-Shy Franchise
The allure of the Mariners has always been there. The talent, the personality, and the excitement have come from many players and teams throughout this franchise's history. However, they have never been able to get to the promised land.
Every time Seattle seems to be able to get within reach of the mountaintop, there has always seemed to be an immediate drop-off. Most notably, the teams of the 90s were teeming with talent but got completely broken up without a single championship run.
9. Pittsburgh Pirates: Two Decades of Despair
This franchise plays at a stadium that is so highly regarded that you would think at least some of the happiness came from winning seasons. Unfortunately, from 1993 to 2012, the Pittsburgh Pirates went through a drought of 20 straight losing seasons. Right before that streak, they traded the greatest slugger of all time, Barry Bonds, and lost out on his legendary seasons.
8. Baltimore Orioles: The Angelos Era
Don't get me wrong, there are many good years of Orioles Baseball throughout history, but a streak of bad seasons in the Peter Angelos era marred this franchise.
Through the last few years of Cal Ripken Jr.'s career and the rest of the first decade after the turn of the century, Baltimore did not see winning baseball. Even as the organization saw more success after 2011, they have not been able to make the deep playoff run that its great fan base deserves to see.
7. Oakland Athletics: Moneyball Gone Wrong
It's no surprise that we find the Athletics on this list, and that is sad to say. Some of the coolest players have come from this organization during the Moneyball era. But we have to learn how truly cool they are when they ultimately end up on other teams.
I always like to tell my film friends who love the movie Moneyball that it's a fun movie. However, the fun pretty much stops after the movie ends.
6. Montreal Expos: A Canadian Tragedy
Sure, I'll say it. I thought the Montreal Expos could have built a dynasty. I'm sure a lot of people would have liked to see baseball thrive in that city. There are still murmurs from those who want to bring the game back to Montreal.
From Andre Dawson to Gary Carter to Pedro Martinez and Vladimir Guerrero, the Expos had so many stars on their side. But from 1969 to 2004, Montreal only saw the playoffs in one season. That is a tragedy.
5. Kansas City Athletics: Yankees’ Farm Team
The Kansas City era is almost like a fever dream for the Athletics franchise. Many know of the early success in Philadelphia. Many remember the heights they reached in Oakland. But few even want to acknowledge their time in Kansas City. There was never a winning season during those 13 years.
In fact, the owner who moved the A's to the city, Arnold Johnson, was a close friend of the Yankees' principal owner and made a slew of trades until his death in 1960. It's a forgotten era, and I'm sure many are fine with it staying that way.
4. St. Louis Browns: Perpetual Cellar Dwellers
With all the rich history the Orioles have in the twentieth century, many forget that they weren't originally in Baltimore. This franchise started as the St. Louis Browns, who actually moved from Milwaukee, as they were the original Milwaukee Brewers, but that history goes back to its current iteration.
The Browns saw a lot of losing throughout their history from 1901 to 1953. They only achieved one 90-win season and saw the World Series one time.
3. Florida/Miami Marlins: The Fire Sale Kings
South Florida has seen great teams twice. Pretty much only twice. One of the more frustrating transformations of a World Series team came after 1997. Their ace, Kevin Brown, left for the West Coast to eventually become baseball's first $100 million player.
All-Star Moises Alou left along with Al Leiter. Then they traded Gary Sheffield and Bobby Bonilla in the middle of the next season. Before we knew it, the best team became the worst team.
2. Cleveland Spiders: The Ultimate Disaster
It's not how it started; it's how it ended. For most of the 1890s, the Cleveland Spiders were a good franchise. They made it to the World Series once and featured a young pitcher having some legendary seasons named Cy Young. But it all came crashing down in 1899.
The Cleveland owners made a decision to buy the St. Louis franchise in the National League, which would eventually be called the Cardinals by 1900. Everybody, including Cy Young, got shipped over to St. Louis, and Cleveland was left to implode. Implode they did, with a 20-134 record.
1. Philadelphia Phillies: Three Decades of Despair
By now, we may look at Philadelphia as a proud franchise with a number of amazing players in its history. However, a 30-year stretch from 1918 to 1948 was a struggle that no other franchise has ever endured. It is well documented that this infamous stretch saw only a grand total of one winning season. 16 other seasons saw the Phillies dead last in the standings.
They were second to last seven other times. Luckily for the city of Philadelphia, the Athletics had some really good seasons in the late 20s and early 30s. Even better, the Phillies eventually figured it out and won some championships of their own.
