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Jason Mackey's MLB winter meetings chat: 12.11.25
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Jason Mackey
12:47
I would absolutely love it. That was my pie-in-the-sky from the start. With that offer to Schwarber, they're telling us they can afford it, too.
Sam C
12:47
What would you say the chances are that their payroll exceeds 100M this season?
Jason Mackey
12:48
Certainly looking better after Winter Meetings. Schwarber offer and Soto would've basically done it. And I don't think they would have been done at that point.
Deb
12:48
who might be the starting LF this year? The password is a nice prospect but not ready for MLB yet and they don’t have any other internal options.
Jason Mackey
12:49
A free agent or trade. Agree that I think Password will be in the minors. Unless he really surprises in spring. But I think it's going to be someone they trade for or sign. Bader, Kepler? Same group I've been citing.
Cullen
12:50
The more I think about it,I believe we need to sign a cheap innings eating lefty regardless of whether we trade Keller, and perhaps 2 guys if we do trade Keller. We're likely going to be trading from pitching depth in one way or another and i want to give prospects some runway, but I think it would be smart to being in a guy who can guarantee 120-150 innings to hedge against injuries, regression, etc. What do you think? Also would Quintana be an option to return?
Jason Mackey
12:50
Wouldn't be against that, Cullen. And, yeah. If we're gonna describe him as an option, I think that's fair. Kind of depends on what they do. It would not surprise me at all if they signed a starting pitcher via free agency this winter.
scoman
12:51
What order would you put these pitchers ranked on you not wanting to trade: Barco, Jones, Burrows, Ascraft?
Jason Mackey
12:51
Ashcraft, Jones (this is probably a moot point), Burrows & Barco.
Mark Topoleski
12:51
Let's rewind and talk about last year for a second. What happened? Why did they do nothing besides various bandaids? Why are they only seeming to try now? Did the sell the team chants actually work?
Jason Mackey
12:52
Ha. I asked Ben Cherington that exact question. Can't say the answer was any good. But here it is:

"I don’t feel like I personally feel any different than I did at the end of the season as far as the way we were looking at the team and the opportunity that we see in front of us. Of course, you have to go through the work and have those conversations internally to get a little bit further along into the strategy. Like, ‘OK, this is more specifically what we’re going to pursue, what we think fits that.’ If we can execute on this, we think this has the biggest impact.’ More specific things take some more time, so maybe that’s where it’s coming from, that we’re just deeper into that now. It’s into the execution phase now. Maybe that’s what feels different. I don’t personally feel, in terms of the way we looked at the team at the end of the season and what we hoped to do that anything’s changed. But we’re in that more targeted phase now."
12:53
My own opinion: I think they realize they have to do something here, otherwise it's gonna get real ugly. Or, uglier. Fans, planes, chants and signs. Local politicians bothering them. MLB and the MLBPA taking issue. And, what happens with a potential lockout and cracking down on small-market teams not spending. I also think there's some frustration because they haven't done enough under this regime to maximize Skenes.
Cullen
12:54
I was listening to one of DK's pods this week and he said something that amazed me. He essentially said GMBC was not surprised at all that the rebuild has taken this long and everything has gone basically to plan. In your dealings with Ben do you get that impression?? I understand that when he took over the franchise we were in a pretty big mess and he had to build nearly everything from the ground up. 7 years is a bit excessive in my estimation...
Jason Mackey
12:55
I don't agree with that. I know Ben had a further-out timeline than fans. But it wasn't 2026. They wanted to win last year and thought they could win. They were obviously wrong and did dumb stuff. But it's not like they had this year circled the whole time.
Wayward
12:55
Who holds more perceived value, Ashcraft or Burroughs?  I love Ashcraft if can stay healthy.
Jason Mackey
12:55
Depends on the acquiring team. They employ wings of people to determine that for themselves. My guess would be Burrows, but it's usually team-specific.
Mark Topoleski
12:56
Undervalued. A pitcher who's shown ability and has 6 years left should be waaay more valuable than Keller
Jason Mackey
12:56
Gotcha. I like Burrows, but he's also coming off TJ and doesn't have a super lengthy proven track record of performance.

Also, do we definitively know one's gonna fetch a better trade return than the other? I don't.
Paul
12:56
What reunion sounds most realistic: McCutchen, Marte, Bell? Do any make sense?
Jason Mackey
12:58
Cutch makes the most sense. I don't know if it'll happen -- very awkward topic for everyone this winter -- but I don't see a point in the other two; they can and should do better. With Cutch, it would be about finishing this right. Final year, part-time role, say goodbyes, let us celebrate you, etc. But he can't be getting 400-500 at-bats. That's not fair to either side. However, Cutch deserves to go out the right way, and the Pirates bear that responsibility -- within reason.
Jeff
12:58
Do you think this is Cherington’s last season if the team finishes under .500 again?
Jason Mackey
12:59
There could be some context there -- like, are they just crazy hurt and go 80-82? -- but the leash isn't long, if that's what you're asking.
Dom
12:59
Any chance Bellinger might be an option for the FO?
Jason Mackey
12:59
Option to check or consider, yes. Likely, no.
Commissioner
12:59
The Pirates have only themselves to blame for free agents not wanting to come here. They’ve shown time and time again that winning is not a priority. That means their best chance of getting legitimate hitters is through trades. Until they do something of substance rather than just talk about it, my skepticism will remain sky high. I certainly don’t think I’m in the minority with this opinion.
Jason Mackey
12:59
Didn't catch a question in there, but I don't disagree with you. Have to win and make this place attractive. They haven't done that.
PC
12:59
Do you think the Oviedo trade could end up looking like the Quinn Priester for Yorke trade?
Jason Mackey
1:01
It could. Don't think that's likely, though. Garcia is a different type of prospect than Yorke. I do think Oviedo could be very good, but you also have to give to get. As long as Garcia produces, whatever.
Brendan
1:01
Hi Jason - with the Pirates not able to be in the draft lottery next year due to the CBA rules, do you think that is sort of behind the push to spend more money/encourage them to go their version of “all in”?
Jason Mackey
1:02
I don't think that's why they're doing this. And, to be fair, they haven't "done" anything. I just think there are other factors before that one informing their actions, such as they are, so far.
Bob
1:02
Does Nutting see any potential monetary benefits to signing one of the Japanese hitters? Opening up a new market to buy merchandise and get eyes? I'd imagine Jung Ho Kang helped some.
Jason Mackey
1:03
I don't think they're against it. They've shown interest in both big guys. They offered Schwarber legit money. It's still there. I don't think they would offer either Japanese star like $5 to play here.

That stuff is part of it, but it's still secondary. Your lineup isn't good, and you're trying to add better hitters.
Jeff
1:03
Players don’t get paid during lockout no matter what the terms, correct?
Jason Mackey
1:04
Regular salaries, that's correct. They still get still get deferred money, signing bonuses, option buyouts & and termination pay.
Mike
1:04
Do you think this will be a one year thing being aggressive then back to dumpster diving? I’m worried it will be only one year
Jason Mackey
1:04
If it works and they're good, no. I think it will stick. If they stink, there's a lockout and nothing changes ... that part worries me.
GPT
1:05
Would signing Suarez, Kepler, and trading for Lowe be a reasonable outcome for the Pirates?
Jason Mackey
1:05
I would sign up for that in a heartbeat.
Paul
1:05
Who made the decision that Cutch can't be an every day left fielder?  His bat is not productive enough to be a DH, but it is enough for an every day left fielder.
Jason Mackey
1:06
I think his body did. Even Cutch has said he can't physically play OF every day. Now, could they use him more out there? Yes. Don't know why Ronny Simon and Alexander Canario were used ahead of him. That's dumb. But he's not an every day OF anymore. He's admitted it.
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