The Pirates enter this winter on a quest to augment their offense in a way that could allow them to contend while superstar hurler Paul Skenes is still in town. Skenes is backed by a solid group of pitching options, including veteran Mitch Keller as well as young arms like Braxton Ashcraft and Bubba Chandler in the rotation along with closer Dennis Santana in the bullpen. That deep array of pitching options has virtually no support from the offense, however; while Bryan Reynolds and Oneil Cruz certainly have the capability of being quality regulars in the lineup, only Spencer Horwitz (119 wRC+) and Joey Bart (101 wRC+) were actually above average hitters for Pittsburgh this year.
That leaves the team in need of help in the lineup, and they appear to be unusually willing to dip into free agency to get it. The team had interest in Josh Naylor before he re-upped with the Mariners and has even shown interest in star slugger Kyle Schwarber. A deal at or approaching $100MM would be virtually unheard of for the Pirates in their team history. Reynolds’ $100MM extension is the only nine-figure deal in history, and their next two richest deals (the $70MM range for Mitch Keller and Ke’Bryan Hayes) were both extensions as well. Francisco Liriano’s three-year, $39MM deal from the 2014-15 offseason remains the largest free agent expenditure in team history more than a decade later.
While the Pirates have indicated they have more financial flexibility than previous offseasons and their interest in Schwarber indicates at least some willingness to spend, it would be understandable for fans in Pittsburgh to take the stance that they’ll believe ownership would greenlight that sort of financial outlay when they see it. Adding a top-ten free agent in this year’s class isn’t the only way the Pirates could improve this winter, however. Ken Rosenthal and Evan Drellich of The Athletic reported yesterday that Pittsburgh is also looking at players like Ryan O’Hearn, Jorge Polanco, and Kazuma Okamoto as “perhaps more realistic options” to bolster their lineup via free agency.
All three clock in well below Schwarber’s five-year, $135MM prediction from MLBTR’s Top 50 MLB Free Agents list. Okamoto is predicted for a four-year, $64MM deal, while Polanco is predicted for three years and $42MM and O’Hearn is predicted for two years and $26MM. Of that trio, only O’Hearn wouldn’t represent a new record in free agency for the Pirates, and given the fact that the Pirates entered 2025 with three $70MM+ contracts on their books it’s hardly out of the realm of possibility that they could stomach a deal on one of those levels. Any of those hitters would substantially improve the Pittsburgh lineup as well and could combine with Horwitz, Bart, Reynolds, and Bart to create a much more competent offense than the team had this season.
With that said, Rosenthal and Drellich caution that it could be difficult for the Pirates to convince even mid-level free agents like those to sign on in Pittsburgh if they get similar offers from teams with clearer paths towards contention. MLBTR’s Top 40 Offseason Trade Candidates list holds intriguing names like Brendan Donovan, Jarren Duran, Brandon Lowe, and Alec Bohm, all of whom would substantially improve the Pirates’ offense in their own right and allow them to do so without spending significant dollars or the player having the opportunity to turn them down. Of course, a trade wouldn’t necessarily preclude a free agent signing; in fact, if they were to acquire an affordable piece like Donovan, it might actually make them more likely to sign a free agent if players begin to view their path to contention in 2026 as more credible.
How do MLBTR readers view the hints of spending in Pittsburgh this winter? Will they make a splash in free agency this winter? Or, if not, will they at least sign a credible enough free agent to break the record held by Liriano’s deal from more than a decade ago? Will they go high enough to surpass the $70MM range of the Hayes and Keller deals? Have your say in the poll below:

Just give me like 3 decent hitters. That shouldn’t be a lot. Just 3 hitters, that I know will give the Pirates at least a 110 wRC+.
My expectation is they sign at least one of Polanco, Suarez, Okamoto, or O’Hearn, then make sort of a Spencer Horwitz 2.0-type trade. That’s it though, in terms of my expectations.
They’ll do just enough to stay out of the union’s crosshairs
For what it’s worth, Cleveland made it to the playoffs with only 2 such hitters in their lineup.
Admittedly, that’s probably not a formula to emulate as it also requires historic collapses in front of your team in order for that to work.
It was also because the Guardians’ hitters became super clutch in the second half. They had a 141 wRC+ with RISP from the start of July through the end of the season. How well a team does with runners in scoring position isn’t particuarly something you can predict and build around.
They don’t have an All Star hitter like Cleveland has in their lineup.
Even with Jose Ramirez in their line-up, their team OPS+ was only abou 3% better than the Pirates team OPS+.
We seem to need the same things in offense. Hope neither one of us is disappointed.
Starling Marte is a free agent, played for Pittsburgh, hit 111 OPS+ last year, and would be cheap. That could be one. Good vibes guy, too.
I just said to my wife “well, time to visit MLBTR again and ask myself with this finally be the year the Pirates do something?” And it turns out, half of you say no. And half of you are wrong.
Which half are wrong?
Yes.
The most reliable indicator of future behavior is past behavior.
And the answer is No
It’ll probably be more of a puddle than a splash.
What free agent would choose Pittsburgh over someone who can probably offer the same amount? Trade Skenes to the Bronx and call your off-season a success. Haha
A very shallow puddle…even by puddle standards
Is Tommy Pham a splash?
It’s bad when there’s a poll on if the Pirates are going to do much this offseason. This is only legitimate for the Pirates. Franchise is the laughingstock of baseball. Worse than the Rockies or White Sox even the Marlins.
I can’t go with you on “the” laughingstock. “A” laughingstock, certainly, but not “the”. Both the Rockies and White Sox are historically bad with no light at the end of the tunnel. Pirates are a couple of pieces away.
They have been consistently bad for over 30 years except for a couple years in there. Good luck getting a few pieces to make them a contender. They are the laughing stock of baseball and they have been the laughing stock of baseball for years. The Pirates go out of their way to be bad on a consistent basis. I agree they have the foundation of what could be a good team, but I have no confidence in ownership or management to make it work. Maybe you do I don’t.
Again, “a” laughingstock is fine. Outside of a couple of seasons, the Rockies have never been relevant. They have combined a pisspoor MLB team with a pisspoor MiLB system. Hard to do. The White Sox haven’t been relevant since the the iPhone was invented.
The pitching is so good it won’t take much. It is certainly within the realm of possibility.
And this is where the laughing stock part comes in. Like I said good luck getting a few pieces to make them contenders. those other teams might have failed miserably, but they have tried over the years to at least put a decent team on the field. Maybe not right now maybe not consistently but they did try here and there. The Pirates try to be bad and in the last place every year. That makes them the laughing stock.
This is a joke right? There is no answer for 1.50.
The only way to do this is to go all in and to decide to stop being a farm system for other teams- extend Skenes to a deal he can’t refuse, match any large market offer for Schwarber, etc. and just go all in. Only way to do it.
I’ll feel kinda bad for a guy like Bryan Reynolds, who signed his long term extension when the Pirates could convince their players to sign very team friendly deals relative to their traditional budget, but who knows- maybe they’d even re-work Reynolds’ deal to show him that they’re serious about competing and matching the budgets of their competitors going forward.
It could force them to make one of, if not the largest off season layouts of new salary commitments in baseball history.
You want them to give Reynolds MORE money? $15 million a year for a guy who just put up a 99 wRC+ seems plenty.
Said like a true Trillionaire Team Operator.
Anyone who follows the Pirates knows that Reynolds was comfortable with the deal and indeed underperformed significantly this past year.
He is paid plenty of money and they will certainly not be reworking the deal.
Come on BC get this party started! What’s that I hear, Burrows for Donovan of St.Louis????
Trades in-division are rare, and most likely won’t happen on either front.
There will be a lot of competition for Donovan. Don’t know if Burrows will do it, but it should get the attention of Bloom.
The Pirates have the pitching to be a strong team. We shall see if the owners want one.
If they don’t care, we’ll know by the start of spring training.
The Pirates are the worst-run team in all of baseball, and it falls squarely on Cherington and Nutting, who refuse to invest meaningfully in their team. Even the Rockies, Twins, and Angels seem to care more than the Pirates do.
Super- really?
It falls solely on Nutting. Cherington is an employee who has to work within the constraints an owner/boss gives him. If Nitting says here is $10 or $200 million he can do totally different things. They have a great depth at pitching , and have really drafted well recently – that’s working within the *Nutting constraints* of 0 foreign scouts in Asia or Oceania.
Unlike White Sox or Rockies they attempt to improve – and would do so if they had the *guts to invest* like other mid market teams have (see Kansas City or the Brewers)
HAH!
The truth will be, the Pirates will claim to have been interested in “player A, B, & C” AFTER they have signed with new clubs for a lot of money, That way they will look like they were going to spend, but someone else outbid them. It wouldn’t be the first time for the franchise to do that.
I was glad that they did not get Naylor.
Many of these players do not want to sign with a team that is not a proven winner.
Hahahahahahahaha. That is all
Bob Nutting going to spend? No way that’s gonna happen
They will sign a couple who over estimate their market and Piitsburgh are the only ones willing to go multiple years. Then those guys will either perform as expected and be mediocre players or perform and get traded next season. Can’t imagine anyone who is in their prime and looking to compete would seriously consider the Pirates and their history of being one of the most dysfunctional organizations in sports.
They won’t even make an offer to anybody. They’ll keep saying that they were “interested” in every player who signs elsewhere, though!
As Pirates fans, we’ve heard this repeatedly
I have to thank Nick Deeds for writing the article but most of us would say, “I’ll believe it when I see it”
That said, one player isn’t going to do it. This team is deficient in multiple positions and almost completely anemic at the plate.
A splash in the toilet, maybe
MLBPA probably threatened them with sanctions if they didn’t have an active free agency. Nutting hasn’t spent on FAs since Obama was in office.
Not really a good poll when we already know the answer. Maybe they just wanted to see how many fans were drinking Cherington’s Kool Aid.
It’s good to put them on the spot like this
They won’t spend if they can help it but might to stop grievances.
They need 3B, LF & 1B ! Sign O’Hearn (13mil), sign Okamoto(14mil), trade Keller or Burrows or Oviedo for Adell or Duran. May sound crazy for the Bucs but they can’t waste this pitching staff !! If it’s Keller they save 16 million there
I’m dubious on Okamoto, and Adell on defense would be a disaster. Look at his numbers in CF, and then recall that PNC Park essentially has two center fields. I think Duran would require more than what the Pirates would require. I don’t think just what you mention would get him – especially after they just got Sonny Gray.
They,if they want to take advantage of the time frame of Chandler-Skenes being cheap – they can’t (because they aren’t contenders yet) the top tier of FAs nor is Me Nutting willing to pay that level either.
Thus their best options are either *diamonds in the rough* – the Japanese FA’s who may pan out or not but definitely will be cheaper than MLB ones or flawed players – be it young ones who can be fixed (hopefully) or those that could rebound.
I think they should go after Okamoto who does have some power and can play passable 3B. And maybe dangle a Duran for Keller swap as the Sox have a surplus of OF and claim they need a #2 behind Crochet . And possibly swing some FA signings of established but tier 2/3 (after the top 20) players rather than retreads.
Don’t think Keller alone will get Duran, but Duran would help the Pirates a lot.
Good luck getting him (I hope you do).
It would be fun having the Pirates much better than they have been.
It is far more likely that an elephant will grow wings and then fly from India to Iceland than it is for the Pirates to provide a player a contract in excess of 39 million dollars.
OK here’s what I would do if I could wave a magic wand and become GM for a day:
1) See if I could trade O’Neill Cruz and (probably a prospect would be needed) to pry Justin Crawford out of Philadelphia. It upgrades CF defense. It’s true that Crawford doesn’t have nearly the power that Cruz has, but if Cruz never makes contact the power doesn’t mean anything lol.
2) Try to get Kwan out of Cleveland. I wouldn’t mind an Oviedo or similar to get him. Stick him in LF. He could handle the LF in PNC.
3) Try to beg Andrew McCutchen to fill the Alexander Canario role from ’25.
4) Make Jared Jones the closer.
5) Go all out to try to get Schwarber and see if I can get him to play 1B, and move Horwitz to 2B.
6) Konnor Griffin is opening day SS unless he completely wets the bed.
7) Whenever there is a homer at PNC Park, the PA puts on the goal horn from the Penguins.
8. At the end of Bucs home wins, there is a pirate ship in the river with the Pirate parrot waving the Jolly Roger.
That was fun! Thanks for reading lol. .
I’d they win the draft lottery that’ll them more confidence to go for it
Make a splash like a cannon ball dive – NO. Jump in with the yellow duckie waist float and arm floats, probably.
If you count J.J. Bleday as a splash.
I would be happy with a non-roster invitee to Spring Training (ironically enough), but anything bigger than that and I (and many others) would have a problem.
They go $100+ to appease the PA.
In the past I’ve googled the cost of that horn! Totally doable! But hopefully the other things on the list would ensure it would actually be used haha.
I would imagine pirates try to extend Chandler and/or Griffin rather than spending too much on feee agency. Maybe even Barco. The Skenes ship has sailed.
Splash right into Randal Grichuk. One year, $7M…