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Jason Mackey's Pirates chat: 11.13.25
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Jason Mackey
11:48
Hello, everyone. Welcome to my weekly Pirates chat. Good to be with ya. We'll get started at noon, but feel free to fire away with your questions now.
12:06
And away we go ...
Pirates
12:07
Jason, who had the best CY YOUNG season for the Pirates - VERN LAW, DOUG D. or PAUL SKENES?
Jason Mackey
12:09
This might not be terribly popular with the old crowd, but it's Skenes. By a mile. Drabek and Law were both worth 4.2 bWAR, Skenes 7.7. I understand the win total isn't there, but Skenes also wasn't given as much of a chance to get the wins and played on a much worse team -- which he can't control. They're all great, but I just can't past Skenes doing what he did this year, at his age, with all the attention, etc. Very impressive.
music
12:09
Jason, I saw a documentary recently showing how tight Jerry Garcia was with the Hells Angels. What's the deal with that? They don't seem like they'd match up
Jason Mackey
12:11
Couple things, quickly, because I'm sure everyone doesn't want to hear about this. Ha. But one link is hating rules. Another is what Garcia would say about good vs. evil. You can't have one without the other. I think it helped inform his feelings and lifestyle. Believe they also saved Jerry's life at one point.
music
12:11
one more music question - is there a limit to how long walkup music can play at MLB games? and, if so, what is the limit?
Jason Mackey
12:11
It can play for roughly 10 seconds and ends when the batter get into the batter's box.
Cullen
12:23
It is being reported that the Pirates could spend $30-40m this offseason. From your understanding, does that number include arb raises + Keller trade + signings or will the entire $30+ be allocated to players not on the roster independent of everything else? If that number doesn't include a potential Keller trade could we maybe see that number trend closer to $50m?
Jason Mackey
12:24
Hey Cullen. My understanding -- and I've said and written this before -- is that payroll will be around what it was last year, given or take say like $5 million. And I'd be shocked if it was $5 million lower. So, yeah. They're roughly the same statements. Payroll will land around $95 M if I had to guess. How they get there ... probably depends on viability of a Keller trade and how it makes the most sense to acquire bats.
Cullen
12:25
How much SP would you be comfortable moving for bats this offseason? Between major league ready prospects, guys coming back from injury, and nailed on starters in the rotation we have 9 guys for 5 spots. The Dodgers proved how important pitching depth is but we clearly need bats, what is the right balance?
Jason Mackey
12:27
I'd be fine trading Burrows, Harrington or Barco. I'd listen on Chandler & Ashcraft, but my line would be stupid high. Nobody would meet it. Oviedo I kinda want to keep. I think the return would be small because of TJ, and I think he could actually be really good. As for Keller, I don't want to trade him. But he's a proven MLB starter who eats innings and gives you professional starts more times than not. There's value there. And I don't think it's a dumb idea for a team in drastic need of offense to spend more of its money there. So, I'd certainly be open to  Keller deal if it was offered.
Cullen
12:28
What would need to go right for Konnor4real to break camp with the big club in 2026?
Jason Mackey
12:29
A contract extension would be the easiest thing. I'd love to see the Pirates do that. Even if they don't extend Griffin, I've been thinking about this lately: If he's their best option ability-wise, why shouldn't he be there? He works cheap. There damn sure better be urgency. I'd like to see an extension, don't get me wrong. But just letting him earn it in ST is perfectly logical.
Joe Starkey
12:29
I'll give you $1 million if you can accurately predict the three most impactful additions the Pirates will make this offseason. Not could or should, will.
Jason Mackey
12:33
Good afternoon, Dr. Starkey. I'll go with a trade for Brandon Lowe and signing Cedric Mullins and Gregory Soto via free agency. Could wind up trying Nick Gonzales at 3B or playing Triolo there. Not a super natural fit, but there's something about Lowe that I can't shake.
Jim M
12:33
Jason, With the Pirates offense finishing near the bottom in most categories the last few seasons and Ben Cherington’s job theoretically on the line, is it possible (hopefully likely) that the team’s hitting philosophy will become a shade more aggressive? Especially with 2 strikes ? Maybe more of Don Kelly’s “Line Drives to the Outfield” ?
Jason Mackey
12:34
I'm not sure it's that simple -- their philosophy isn't to strike out; what you're seeing is a failed execution of their philosophy -- but obviously something needs to change and fast. Agree there.

They need to do a better job individualizing stuff, and I think they will. Let guys be themselves. Don't overcomplicate stuff. Don't be as quick forcing adjustments. Lot of things they can do differently. It's not as simply as a two-strike approach.
Mark
12:35
Hello Jason.  We all know that the Pirates need an upgrade over all eight everyday position players.  But, who are the top two that you are most comfortable with not replacing?  Thanks.
Jason Mackey
12:36
Spencer Horwitz was objectively fine at 1B. There's also context here, Mark. Reynolds is under contract. They're not gonna cut bait on Cruz. Bart will be here; they just need to do a better job deploying him. Henry is a 1-1 pick that the pitching staff really likes. They need an OF and 3B, no doubt. A SS, too, although that could be Konnor Griffin.
CrazyRoosterCrowAtMidnight
12:36
is anyone besides Keller being actively shopped? The Hells Angels were better security for the Grateful Dead than the police. The symbiosis makes sense to me - many outlaw themes within the music and a general sense of “don’t tell me what to do” between deadheads and bikers.
Jason Mackey
12:38
I agree with you there on the Deadheads/Hell's Angels. We all hate rules.

I wouldn't even describe Keller as "actively being shopped." If the return isn't there, they could absolutely keep Keller. They're just willing to listen maybe a little more because he's good, and they're gonna need to acquire bats somehow.

Bottom line, Pirates are willing to listen on anyone. They've always been like that, as they should. There's just no darn way they'll do anything with Skenes, and the line on others is also very, very high.
Pat
12:38
Does having Skenes actually motivate ownership to invest in the team, or is it business as usual in Wheeling, WV
Jason Mackey
12:39
Probably somewhere in the middle. They haven't shown enough urgency, IMO, so I'm not gonna sit here and say having Skenes actually motivates ownership. But I've also been around enough to know how frustrated they are with where they sit. It's somewhere in the middle.
Brandon
12:40
I think the pirates need 3-4 hitters to compete this year. I think the pitching will be top 5, but they really need hitters. I don't think it would take much to trade for Taylor Ward and I think Duran would be a great guy to trade Keller + for. Taylor is projected $11M in arbitration and Duran $8M thats only adding $3M increase in payroll. From there you could go get a veteran lefty to fill out the rotation and go get some other smaller pieces and maybe one big one like Suarez or one of the Japanese guys. What are your thoughts on what they will do?
Jason Mackey
12:41
Ward and Duran make sense, but I don't see both happening. Where would you play guys? They're gonna keep Reynolds & Cruz. The add in the outfield should be one.

You need a lefty reliever. Not as attached to someone in the rotation, but I wouldn't turn it down.

They need someone with leadership qualities among position players. Miles on the tires, so to speak. And obviously 3B has to improve a bunch.
PrinceBob
12:42
Do you have any idea what gamblers can use as hooks for NBA and MLB players? I can see where a couple thousand dollars could have been tempting when player salaries were low enough that guys needed off season jobs. But even for guys on minimum salaries what gamblers can offer is pocket change. Is it the thrill of gambling? Maybe. But none of these guys are actually gambling. They're giving inside tips about line ups or deliberately throwing their first pitch for a ball. Do you think they're being blackmailed?
Jason Mackey
12:42
I have no idea on this one. Honest to God, I've never bet on sports, don't know how to bet on sports and don't want to bet on sports. I'm a terrible person to ask. But, yeah, I can't see why you would risk all that for $12,000. Insane to me.
Jason
12:42
You are wearing Cherington’s shoes. What are the first 3 moves you are making right now? Could be coaching/staff related, calls on acquiring a potential player for trade, scouting or attacking a certain area to upgrade, or a specific free agent that you would love to see wearing a Bucco uniform.
Jason Mackey
12:43
I might buy new shoes because my feet would hurt. I'm 6-foot-4, Jason. Seriously, though, can you clarify something for me: Are these reasonable moves or literally anything in the world?
Wayward
12:43
Jason, are the Pirates hitting staff involved in the guy's offseason work? If so, to what extent?  Thanks.
Jason Mackey
12:45
Not really, Wayward. They can be. Sure they are for some. But most have private people/facilities. It's amiable. Pirates work with them; there's a healthy exchange of info around the player. Team might have something it wants the player to work on, for example. Certainly not a contentious thing.
Jake
12:45
Any evidence whatsoever about a potential Paul Skenes extension? I get it, probably unlikely.
Jason Mackey
12:45
None. There has been no momentum and very little "discussion," if you wanna call what occurred discussion. It's a non-issue until the Pirates win.
Jonathan
12:45
With Cherrington being on record this week saying this is the most flexibility he's had with payroll and trades, what do you think that actually is? I know you've stated you think it'll be between 90-100 million. Does that still feel the same to you or maybe more after these comments?
Jason Mackey
12:46
I still feel the same. Got this above. Have written/said around last year, maybe a little above. Said earlier I'd guess around $95 M, which tracks with current news.
John Rambo
12:46
Jason, who's the starting 3rd baseman on opening day?
Jason Mackey
12:47
I said earlier Brandon Lowe trade, so that would probably mean Jared Triolo. Could be anyone, though. If they get Jordan Westburg, him. Don't think it'll be Eugenio Suarez. Alec Bohm would make sense as well.
Pablo
12:47
With one of the best rotations they’ve had in decades, was the final record last season the official low point of the Nutting era? And is there any light at the end of the tunnel? Even an average lineup should propel this team into post season contention.
Jason Mackey
12:49
Not the low point, no. Be careful there. And, yeah. I think there's plenty of light at the end of the tunnel. Did you see J.J. Cooper from Baseball America yesterday did a piece on teams with the level of stardom the Pirates could have with Paul Skenes and Konnor Griffin. Those teams almost always win.

I don't want to steal J.J.'s thunder -- BA is an awesome publication & resource for all of us -- so just check out the article here: https://www.baseballamerica.com/stories/can-the-pirates-fail-with-paul...
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