Some MLB teams carry themselves like the world owes them a World Series ring, whether they’ve earned that attitude or not. Whether it’s fanbases acting like October is a birthright, front offices making splashy moves with sky-high expectations, or franchises still clinging to past glory, baseball has no shortage of entitlement.
Over the last three decades, a few clubs have mastered the art of walking into every season with swagger that doesn’t always match the results. These are the 15 most entitled MLB teams of the last 30 years, ranked from eye-roll-worthy to full-on delusional.
15. Toronto Blue Jays
The Jays talk like perennial contenders every spring, then forget how to hit in October. Their roster always looks great on paper, but the postseason results don’t back it up.
14. Philadelphia Phillies
This team swings big, spends big, and lets you know it. But even when the results come, it’s like they think they invented grit.
13. San Diego Padres
They’ve been acting like a superteam ever since the checkbook came out, but not much has translated into wins that matter. The vibes are strong, the rings are not.
12. Chicago Cubs
The 2016 title broke a curse, but also created a weird sense of superiority. Cubs fans waited 108 years to get arrogant and then never looked back.
11. Los Angeles Angels
They had two of the best players of this era and almost nothing to show for it, but somehow, they still walk around like a powerhouse. Maybe it’s the Anaheim air?
10. Houston Astros
Yes, they’ve been dominant. But when you get caught cheating and still play the victim? That’s peak entitlement.
9. Texas Rangers
They won it all recently, but the vibes have been loud for years—big spending, big expectations, and big energy. It’s like they skipped a few humility steps.
8. St. Louis Cardinals
The self-proclaimed keepers of “The Cardinal Way” love to lecture everyone else on how baseball should be played. Meanwhile, the game keeps evolving, and they’re still stuck in 2013.
7. Boston Red Sox
They broke their curse and immediately became insufferable. Now they cycle through chaos, payroll cuts, and front office drama like it’s part of the plan.
6. New York Mets
Somehow both cursed and cocky at the same time, the Mets always expect the world and rarely deliver. Every offseason is a parade of hope, followed by injuries, weird vibes, and disappointment.
5. Atlanta Braves
Yes, they’ve been very good lately. But the fanbase acts like a dynasty is already secured—and ignores the decade of playoff underachievement that came before it.
4. San Francisco Giants
Three rings in the early 2010s gave them all the swagger they could handle. Now, every time they lose out on a free agent, it’s treated like a national crisis.
3. Los Angeles Dodgers
Yes, the Dodgers won it all last year. However, they act like they should win the World Series every single year, no matter what.
2. New York Yankees
The Yankees still operate like it’s 1999, and anything less than a ring is treated like a national tragedy. The fanbase brings championship energy—even when the roster clearly doesn’t.
Read More: The 15 Most Delusional MLB Stars of All Time
1. Chicago White Sox
For a team that’s mostly been dysfunctional, the White Sox still act like they’re above a rebuild. Every move feels like it’s meant to prove something, and none of it works.
Read More: The 15 Most Entitled MLB Teams
