It's easy for any MLB fanbase to dream about the possibility of adding Kyle Schwarber in free agency. The slugger has prodigious power that should age well, and despite being a pure DH, he's one of the most coveted bats on the open market. However, he remains unsigned after his last deal with the Philadelphia Phillies expired, and so the rumor mill is circulating about who's in on Schwarber, who's not in anymore, and about when Schwarber might sign.
Pirates already bowing out of Kyle Schwarber sweepstakes
Remember all of that talk the Pittsburgh Pirates were putting out there about building around Paul Skenes, and potentially being in on Schwarber? Well, to the shock of absolutely no one, Ben Cherington and Bob Nutting have yet to even come close to walking the walk. And that means that they're also reportedly already out on the possibility of pursuing Schwarber in free agency.
According to Alex Coll of Last Word on Sports, the Pirates in the Schwarber market "seem to be all bark with little bite" when it comes to being willing to pony up for the high-priced commodity this offseason.
There's no reason that anyone should've expected anything different, of course. The Pirates are going to be cheap until the exact moment that they prove they're not. And while they may still be more aggressive in free agency than they have been in recent years, the fact of the matter is that going from not handing out deals in free agency worth more than $40 million in total value to handing one to Schwarber worth $30+ million annually is just ludicrous to even consider.
This isn't to say that Schwarber choosing a smaller market team outside of the Phillies or Red Sox or so on isn't in the cards. The Cincinnati Reds, his hometown club, appear to be in the mix still. But the defining difference between them and their division rival, the Pirates, is that they appear willing to loosen up their grip on the checkbook.
Schwarber expected to sign before Kyle Tucker in free agency
Along with Schwarber, the other big bat that's going to be featured in headlines until the moment he signs is Kyle Tucker. While we've already seen the likes of Dylan Cease and Josh Naylor sign, it's fair to say that what happens with the pair of Kyles is the biggest domino that needs to fall in order to really kickstart free agency. And as of now, it seems like Schwarber could be the one to get the ball rolling.
According to ESPN insider Jeff Passan on Threads, Schwarber "might be the likeliest of the big free agents to sign first". That notion was furthered by MLB Network insider Jon Morosi on Monday as he said that, while we could have to wait until the start of the Winter Meetings before either player signs, he expects Schwarber to sign before Kyle Tucker.
.@jonmorosi says he expects Kyle Schwarber to sign before Kyle Tucker:
— MLB Network (@MLBNetwork) December 1, 2025
“Neither one of them will sign this week... [I] feel like we're heading towards a Winter Meetings signing extravaganza.”
We are less than a week away from the 2025 Winter Meetings 👀 pic.twitter.com/wdoL8cxNMx
What does that actually mean other than we have to wait less time to see which team Schwarber will suit up for, presumably, for the remainder of his career? Well, it actually probably has a lot to do with the Phillies.
While we'll talk more soon about where the Phillies and Schwarber stand, if they were to lose their All-Star DH this offseason, that would likely put them in position to make a more aggressive pursuit for another big-ticket item like Tucker. Similarly, another suitor like the Boston Red Sox could pivot from Schwarber to someone like Pete Alonso in their pursuit of a big bat this offseason. And that holds true for virtually every potential suitor.
As for Schwarber himself, it could go either way in terms of whether signing before Tucker would benefit him or not. On one hand, waiting out Tucker could make his demand even higher. On the other hand, however, showing urgency could ensure having the most possible options to get the best fit for the rest of his career.
Phillies 'remain the favorite' for Kyle Schwarber on the open market
Back to Passan's report on Schwarber, he also noted, importantly, the current hierarchy when it comes to the left-handed slugger's suitors. And while the familiar cast of teams we've heard throughout the offseason — the Red Sox, Reds and Mets — are joining Philadelphia in the free agency sweepstakes, the Phillies "remain the favorite" to sign him.
This is consistent with what we've heard throughout the offseason to this point, for whatever that's worth. Schwarber was a stud before he ended up in Philadelphia, but it's also the place where he found somewhat of a long-term home, a place where he's beloved by the fanbase, and a ballpark where he's obviously comfortable and has put up tremendous numbers since 2022.
That doesn't mean it's going to be a walk in the park or even that Schwarber would take a hometown discount, though. The other key piece of Passan's reporting is that the years and money are going to be large when it comes to Schwarber's free agency. Not that Dave Dombrowski has any kind of history of cheaping out, but if he were to not offer something commiserate to what other suitors are, then that could change the math here with who's the favorite for his services.
It does seem, though, that Schwarber is part of Plan A for the Phillies this offseason, and Passan's report does confirm that. As mentioned when discussing Tucker, though, it'll be fascinating to see what Philadelphia missing out on Tucker would ultimately lead to.
