Most Heartbroken MLB Franchises Since 2000: Fans Put To Test In Pittsburgh, Colorado

By Bill Speros Nov 12th, 2025 1:28 PM EST

Aug 3, 2025; Denver, Colorado, USA; Colorado Rockies fans with bags on during the fourth inning against the Pittsburgh Pirates at Coors Field. Mandatory Credit: Ron Chenoy-Imagn Images

Winning may not be everything, but it makes loving your favorite Major League Baseball team easier. The Chicago Cubs and Boston Red Sox remained lovable losers for decades, before each won championships in this century. Other teams simply lose. And they do it without generating any passion. So, what are the “Most Heartbroken MLB Franchises Since 2000.”

Bookies.com used data from Stathead.com and online fan sentiment analysis (from Reddit.com and X) to create a scoring system that factors in number of playoff games, World Series wins, regular season records, and fan sentiment to rank the MLB teams with the most heartbreak. The data measures the 2000-‘25 seasons.

The "Most Heartbroken MLB Franchises Since 2000" are the Pittsburgh Pirates, Colorado Rockies, San Diego Padres, Cincinnati Reds, and Milwaukee Brewers. Of these five teams, only one (the Rockies) has reached the World Series in this century. And in that case, Colorado got swept by Boston in 2007.

Most Heartbroken MLB Franchises

Here’s our data-driven breakdown of all 30 MLB franchises ranked form the most heartbroken to the least.

Making Sense Of The Numbers

The five “least” heartbroken MLB franchises in our list have combined to win 13 of the 26 World Series played since 2000. Those teams are the: Los Angeles Dodgers, New York Yankees, Houston Astros, St. Louis Cardinals, and Boston Red Sox.

There are always Red Sox and Yankees fans who – at least on the surface – are never satisfied and often lament their team’s most-recent postseason failures. The highest ranked team among the “Most Heartbroken MLB Franchises Since 2000” to have won a World Series during this time span was the Angels. The 2002 World Series champions carried the name “Anaheim Angels” but have since changed their “20” to Los Angeles.  

Most Heartbroken MLB Franchises: Q&A

Q: How was the “Most Heartbroken MLB Teams” ranking determined?

A: Bookies.com created a custom “Heartbreak Score” using data from Stathead.com, Reddit, and X (formerly Twitter). The scoring system combined team performance and fan sentiment from the 2000–2025 MLB seasons. Each score factors in the number of playoff games played, World Series wins, regular-season records, and how fans express disappointment, frustration, or hope online. The result is a data-driven ranking that reveals which MLB fanbases have endured the most emotional pain over the past 25 years.

Q: Which MLB fanbases are considered the most heartbroken?

A: According to the 2025 ranking, the Pittsburgh Pirates, Colorado Rockies, and San Diego Padres top the list as the most heartbroken MLB fanbases. Each team has had long postseason droughts, crushing playoff losses, and years of unmet expectations. The data shows that while these teams occasionally inspire hope, their fans consistently face disappointment — both statistically and emotionally — making them the true kings of MLB heartbreak.

Q: Why are some MLB teams less heartbroken than others?

A: Teams like the Los Angeles Dodgers, New York Yankees, and Houston Astros rank lowest on the heartbreak scale because of their consistent success and recent championships. Frequent playoff appearances and strong win records ease fan frustration and lower their “misery index.” Meanwhile, smaller-market teams and those with fewer postseason wins tend to show higher fan negativity and emotional fatigue — key drivers of the overall Heartbreak Score.

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