[Bookies.com] Most Heartbroken MLB Franchises – Pirates Rank #1
November 13, 2025
Story breaks down the most heartbroken MLB franchises since 2000. Pirates come in at the very top.
6 comments
Hell yeah! We won something! Hang the banner!
It gets harder to break a heart when it’s been dead for so long
Sell the team
I feel like to be heartbroken you have to expect something good to happen.
Hard to argue with it. Where is there any reason for hope? And it’s not entirely because we’re a small market club- small markets have built success! Until ownership changes we are just going to be his cash cow and nothing else.
I said this in another thread, but it’s so depressing that we have pretty much the best young player you could hope for and it doesn’t even matter. The best we can say is “we’ll get to keep him for 3 more seasons and then trade him for prospects.”
I’m 37 years old, and the timeline of my Pirates fandom went something like this:
Vague childhood memories of playoffs with Barry Bonds -> 20 years of being absolute ass (the highlight of this period being a 10 game win streak when I would’ve been 12 or so?)-> one playoff series, 2 play-in losses -> time to rebuild, better hunker down for the next 20 years I guess.
We’re the baseball equivalent of the Sacramento Kings, except the Kings probably have more hope of relevance in the future, given the way you need fewer pieces to actually be relevant in basketball. “The next Wemby” could make the Kings relevant again within a few years, whereas the Pirates basically already have him & there’s still just zero chance for us.
I hope we get to have another run at the playoffs in my lifetime. God bless those of you who actively keep up with the team on a regular basis. I love Pittsburgh, born and raised, but I’m not gonna support what Nutting is doing anymore.
I was at the Steelers Colts game and god damn it, does this city deserve a good baseball team they to bring that same energy into.
Heartbroken is not the word I would use to describe the Pirate fan base. I would say jaded is a better word. Apathetic might even be a better word.
I think we should start having banners made with the year and how much profit they made each year.
We could say they are “the 13 time profit champions of Major League Baseball.” Something like that would get people’s attention.
What’s happening right now with Skenes and the kids from “The Sandlot” is an absolute disgrace and cannot be tolerated by anyone with an ounce of self-respect.
![[Bookies.com] Most Heartbroken MLB Franchises - Pirates Rank #1](https://www.rawchili.com/wp-content/uploads/2025/11/PCp-WAytebF9C8kDjKEnI7mVpPfjcNrqhuUxGOhnAQ-1920x1024.jpeg)
6 comments
Hell yeah! We won something! Hang the banner!
It gets harder to break a heart when it’s been dead for so long
Sell the team
I feel like to be heartbroken you have to expect something good to happen.
Hard to argue with it. Where is there any reason for hope? And it’s not entirely because we’re a small market club- small markets have built success! Until ownership changes we are just going to be his cash cow and nothing else.
I said this in another thread, but it’s so depressing that we have pretty much the best young player you could hope for and it doesn’t even matter. The best we can say is “we’ll get to keep him for 3 more seasons and then trade him for prospects.”
I’m 37 years old, and the timeline of my Pirates fandom went something like this:
Vague childhood memories of playoffs with Barry Bonds -> 20 years of being absolute ass (the highlight of this period being a 10 game win streak when I would’ve been 12 or so?)-> one playoff series, 2 play-in losses -> time to rebuild, better hunker down for the next 20 years I guess.
We’re the baseball equivalent of the Sacramento Kings, except the Kings probably have more hope of relevance in the future, given the way you need fewer pieces to actually be relevant in basketball. “The next Wemby” could make the Kings relevant again within a few years, whereas the Pirates basically already have him & there’s still just zero chance for us.
I hope we get to have another run at the playoffs in my lifetime. God bless those of you who actively keep up with the team on a regular basis. I love Pittsburgh, born and raised, but I’m not gonna support what Nutting is doing anymore.
I was at the Steelers Colts game and god damn it, does this city deserve a good baseball team they to bring that same energy into.
Heartbroken is not the word I would use to describe the Pirate fan base. I would say jaded is a better word. Apathetic might even be a better word.
I think we should start having banners made with the year and how much profit they made each year.
We could say they are “the 13 time profit champions of Major League Baseball.” Something like that would get people’s attention.
What’s happening right now with Skenes and the kids from “The Sandlot” is an absolute disgrace and cannot be tolerated by anyone with an ounce of self-respect.