The biggest issue in MLB in recent years is that only some teams have appeared eager to try to win. Because of this, when a team suddenly makes it known that they're going to start spending money seemingly out of nowhere, it'll take some convincing to get free agents to sign. The Pittsburgh Pirates are a prime example of this.
They're finally willing to spend real money this winter after years of refusing to do so, but the only free agent they've signed over a month into the offseason is Gregory Soto. According to The Athletic's ($) Ken Rosenthal, that's unlikely to change anytime soon because of their reputation around the league.
Why the Pirates will have a tough time signing free agents
"Trades could prove the Pirates’ best path if they repeatedly are spurned by free agents. Kyle Schwarber rejected them, and so could others who prefer to play for more competitive teams," Rosenthal wrote. "Already, one person in the industry has created a term for a Pittsburgh club that might keep finishing as runners-up: 'Pirates-maids'".
It seems likely that for the Pirates to have an impactful offseason, they will need to make trades, which is largely their own fault. On the surface, Pittsburgh would be a nice fit for many free agents. Who wouldn't want to join a team with the young pitching they have and play half the time at arguably the nicest stadium in the sport in front of a passionate fan base? But players aren't all that interested in the Pirates because the Pirates haven't been all that interested in winning for decades now.
If you're Kyle Schwarber or Josh Naylor, two players the Pirates have pursued, why would you go to Pittsburgh rather than take a comparable offer to a team that's proven to be invested in trying to win? The Pirates have a reputation to alter, and that just doesn't happen overnight.
What the Pirates need to do to attract free agents
There are two things that the Pirates need to do to make players and agents believe they're serious about winning. First and foremost, they're going to have to overpay an impactful free agent to come aboard.
Yes, they were competitive in the Schwarber sweepstakes, even offering the same AAV as the Philadelphia Phillies, who wound up bringing Schwarber back. But the Pirates will have to go above and beyond to sign a free agency of Schwarber's status: For example, instead of topping out on a four-year offer for Schwarber, giving him a six-year offer at the same AAV or a five-year deal at a higher AAV would've given Schwarber something to think about. Would these deals age well? Likely not. However, for a team like the Pirates to land a marquee guy, they have to be a little irrational.
Signing Schwarber would've sent a message to the league that they're serious about winning, and could've made it easier for them to add other players down the line too.
The second thing the Pirates need to do is make their willingness to spend a consistent thing. Pittsburgh will become a destination players will want to end up at if they spend routinely. I'm not saying they should spend at or anywhere near the Dodgers' level, but they haven't signed a free agent to a multi-year deal since 2016, when they gave Ivan Nova a three-year, $26 million deal. That's beyond unserious.
They don't have to give out the Shohei Ohtani contract to prove that they want to win. Doing something of note, and doing so more than just once, will make it clear that the Pirates are serious.
Disinterested teams are MLB's problem, not the Dodgers
Ultimately, this further proves that the teams that don't care to make an effort to win are the real problem, not the Los Angeles Dodgers. Again, I'm not saying that the Pirates or other small-market teams realistically can or even should sign Shohei Ohtani to the contract he signed in L.A., but there isn't a single team out there that couldn't have beaten the three-year, $69 million pact Edwin Diaz just agreed to. There isn't a single team out there that couldn't have beaten the three-year, $66 million deal Teoscar Hernandez signed last winter, either.
I mean, this offseason alone, we saw the Cincinnati Reds offer Schwarber a five-year deal worth $125 million. After they failed to sign him, it was reported that they wouldn't express interest in any other high-end free agents this offseason, and that their pursuit of Schwarber was mostly an attempt to boost their ticket sales. If that's true — and nothing about how the Reds have acted recently would suggest it isn't — why would any notable free agent take them seriously? The Reds clearly have money to spend, yet refuse to spend it. Had they done so, they could've been a team to watch in the NL. Now, they'd be lucky to get back to the postseason in 2026.
All of these owners have more money than they know what to do with, yet a select few would rather pocket it than spend on improving their club. That's within their right, but it also makes it clear to free agents that those teams aren't interested in winning. That makes them less desirable.
Instead of getting on the Dodgers, one of the few teams actually trying to win, it's important that MLB fans know that the teams that don't try are the real problem. Those teams that routinely don't try, like the Pirates, are learning what players really think of them this winter, as they're turned away in their first attempt to spend real money in years.
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