Demilio: ‘We Tried’ Not Good Enough for Pirates This Offseason
The pressure was already on the Pittsburgh Pirates this offseason.
Not only is Ben Cherington on the hot seat at his desk in the general manager’s office, but the Pirates have to find a way to capitalize on having the best pitcher in baseball before he inevitably departs in a couple years.
But given the latest rumors early on in the offseason, there’s even more pressure on the Pirates to get deals done.
ESPN’s Jeff Passan dropped a number of interesting tidbits earlier in the week. Among them are that the Pirates pursued first baseman Josh Naylor before he re-signed with the Mariners. Additionally, Pittsburgh is said to be in on Kyle Schwarber, who hit 56 home runs and drove in 132 runs for the Phillies in 2025, and are keeping tabs on Munetaka Murakami and Kazuma Okamoto – the top two Japanese hitters available in free agency this winter.
For now, it appears as though the Pirates are willing to shop in a different aisle than they usually do.
In franchise history, the largest free agent contract ever given by the Pirates was a three-year, $39 million deal to bring back Francisco Liriano in the 2014-15 offseason. The largest contract they’ve signed an external free agent to was Russell Martin (two years, $17 million). The last offseason the Pirates signed a free agent to a multi-year contract was in 2016-17 with Ivan Nova (three years) and Daniel Hudson (two years).
That needs to change, and if the early rumors are any indication, it could.
Now, do I think the Pirates will end up with Schwarber? No. Even if his biggest contract came from Pittsburgh – which it won’t – I’m sure he’d like to go to a team with a better chance of contending.
Murakami is a pipedream. He’ll get a nine-figure deal that could end up being around $200 million. Okamoto will land a more reasonable contract, but I’m skeptical of the fit given that he’s a pull-happy right-handed hitter which isn’t an ideal profile for a team that plays 81 games at PNC Park each year.
But even if all three of those players wind up elsewhere, the Pirates need to land an impact bat. Now more than ever.
Throughout Cherington’s tenure in Pittsburgh, the Pirates have only ever done modest free agent contracts that have largely ended up having little impact.
If the early indications are that the Pirates are at least involved with some of the top available hitters in free agency, more one-year deals for aging veterans or players looking for bounce-back seasons will not do.
While Passan’s reporting is an encouraging sign, it means very little in the grand scheme of things if no deals come to fruition. Given their history, the Pirates don’t deserve the benefit of the doubt.
For a fanbase that has had very little to cheer about over the last decade — or 30-plus years for that matter — the rumors at least created a little bit of enthusiasm. But in the same breath, expectations have now been raise.
If the Pirates want to land one of the better hitters available in free agency they will need to overpay. Why else would a player willingly come to Pittsburgh if he has equal or better offers with other teams?
Cherington has often used a variation of the same line when discussing the absence of multi-year free agent deals – “We’ve tried.”
Well this offseason especially, trying isn’t good enough. Delivering is all that matters.
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