During the MLB offseason, I was on Twitter talking about the Pirates and their reputation as a small-market franchise that doesn’t know how to win and has an owner–Bob Nutting–with no real desire to try to win.

I contended that, yes, it had been 45 years since Pittsburgh last appeared in and won a World Series (it will now be at least 46 years after the Bucs finished with a 76-86 record in 2024), but what about the Orioles, Reds, Twins, A’s and Royals? When I was growing up, these were some of the most successful and well-run franchises in Major League Baseball. Including the Bucs, these six organizations accounted for 22 pennants and 14 World Series titles between 1969 and 1991. Except for Kansas City, who made it to back-to-back Fall Classics in 2014 and 2015 and won it all in 2015, these once thriving franchises suddenly stopped winning consistently in the early 1990s.

That wasn’t just a coincidence. The Pirates ship didn’t wreck out on some island all by its lonesome following their heartbreaking loss to Atlanta in Game 7 of the 1992 National League Championship Series. Baltimore hadn’t been to the World Series since 1983. The Big Red Machine hadn’t made it back there since 1990. It had been 33 years for the Twins. It had been 34 seasons for the Athletics.

Twitter being what it is, someone chimed in and told me that Baltimore had a much better thing going on than the lousy Pirates. It was an organization that cared about winning, as evidenced by its 101-win season and American League Eastern Division title in 2023. I can’t recall if that person was an Orioles fan or one of those weird baseball purists who doesn’t think MLB needs a salary cap, but either way, I said, “Hold your horses. The Orioles haven’t won anything yet. In fact, they got swept in three games in the American League Divisional Series. Let’s see what Baltimore does while its window is still open and what happens after that thing slams shut in a few years…and it will slam shut in a few years.”

I also pointed out that the Pirates had a nice little run in the mid-2010s, averaging 93 wins a season from 2013 through 2015 and appearing in three straight National League Wild Card Games. Pittsburgh defeated the Reds in the wildcard round in 2013 before losing in five games to the Cardinals in the National League Divisional Series. Unfortunately, Pittsburgh was shut out at home in the wildcard game in both 2014 and 2015 (the wildcard round was just a one-game playoff back then). The Pirates’ window of contending was then slammed shut, and they haven’t been able to pry that sucker open again since.

So, how did Baltimore do in Year 2 of its championship window? It won 91 regular-season games in 2024 and finished three behind the Yankees in the AL East. Still, the Orioles clinched the fourth seed and got to host the Royals in the now best-of-three wildcard round. How did that go? They got swept yet again.

If you’re counting at home, that’s five postseason games for the Orioles in two seasons and five losses.

I’m not pointing this out to make fun of Baltimore and its fans (at least not totally). I’m stating these facts to remind everyone that the Orioles haven’t really accomplished anything on their current run that Pittsburgh didn’t during its three-year run in the mid-2010s. Yes, Baltimore won 101 games in 2023, but the Pirates won 98 in 2015. True, Baltimore has averaged 96 wins a season over the past two years, but that’s only three more than the Bucs averaged during their run. Yes, the Birds won a division title in 2023 and appeared in the ALDS, while Pittsburgh could only secure three wildcard berths after finishing in second place in the National League Central Division for three straight years. However, the Buccos advanced to the NLDS in 2013 and won a couple of games once they got there. The Pirates won three postseason games during their window, while Baltimore has yet to win one.

I’d say it’s a wash so far.

My initial point from back in the offseason remains the same: The Pirates aren’t the only small-market baseball team that must overcome incredibly long odds to succeed.

To repeat: Let’s see what the Orioles do while their window is open and how they react when it shuts.

If you’re anti-salary cap, maybe you’ll choose this time to point out just how successful the Brewers have been in recent years. Define successful. Sure, Milwaukee has won five National League Central Division titles since 2011–including 2024. The Brewers were also a wildcard team in both 2019 and 2020. That’s seven trips to the postseason in 14 years.

Quite the run, for sure. But how many pennants do they have? The same amount that they did before moving from the American League to the National League in 1998: One. That’s right, the Brewers have only been to the World Series once, and that was 42 years ago.

The Brewers’ latest postseason letdown occurred Thursday night when they blew a 2-0 lead against New York in the top of the ninth inning of Game 3 of the National League Wild Card Series at American Family Field. Mets first baseman Pete Alonso smacked an opposite-field three-run homer to right field and celebrated as he rounded the bases. His teammates rushed out of the dugout to greet him at home plate. The home fans sat in stunned silence. New York added another run for insurance, and the Brew Crew could not answer in the home half of the ninth.

It will now be at least 43 years in between pennants for the Brewers and their fans.

But at least they’re trying, right? They’re doing more than the Pirates. I get that.

There are plenty of small-market teams that try harder than the Pirates. The Rays have been the model for small-market franchises over the past 15 or 16 years. But while they’ve appeared in two World Series since 2008, they still don’t have a title to show for all of their supposed code-cracking in a world of haves and have-nots.

The Cleveland Guardians have had quite the run since 1995–including 12 division titles and two wildcard berths. However, Cleveland came up short in its only two trips to the Fall Classic during that time.

The Guardians, champions of the American League Central Division, are set to take on the Tigers in the ALDS. Let’s see how they do this time.

Except for the Royals, another small-market team that swept Baltimore in the wildcard round, the have-nots have failed to win a World Series over the past 33 years. Will Kansas City continue its unlikely journey through the postseason and capture another championship? And if the Royals do win it all, will they have to tear it all down and start over not long after the parade?

That’s what happened after 2015, so probably.

Some small-market baseball teams may be more successful than others, but the vast majority eventually smack their head on a glass ceiling built by the big-market teams and their endless amount of local radio and television revenue.

Small-market teams are still at a huge disadvantage–even once they reach the postseason–and I can’t believe Major League Baseball’s financial system is still widely accepted by sports fans in 2024.