Two Extensions That Could Make Sense for the Twins Right Now

[USAFChief]

1 hour ago, ashbury said:

How did that 15-year contract with Hurricane Hazle work out for the Braves?

You know what they say: Flags Fly Forever. 

[twinstalker]

Quote

That effectively removes Jenkins from consideration, at least until...

You don't need the last part.

I don't know how you buy low on an established pitcher.  He's not going to agree his value is different than it was at this point last year.

Keaschall, though, is a buy-high.  Zero reason to lock him up until he goes back to .290/.375/.460, which he most definitely will.  On the other hand, maybe his representation understands that, but I doubt it.

 

[DocBauer]

I GET the early extension offer idea, but don't subscribe to it in totality. My gut tells me Keaschall and Jenkins will be really, really good players and potential stars. But each was drafted barely over 2yrs ago and each has had some injury setbacks. Can't we wait until each/both have had a single healthy season before we start offering multi year and multi $M deals? Hell, why not offer Culpepper 8yrs and $80M right now?

I like the Jeffers extension offer. I just read today that he's the #4 OPS catcher in MLB over the last 3 or 4 years. And while ERA isn’t exactly a great stat to provide true value for a catchers performance, it's a place to start. And his is slightly better than when Vazquez is the starting catching. That would give some indication that while he may not be a stud defensively, he knows how to call a game and work with the staff. And he's still only 28yo.

The single hardest thing to develop and find in ML baseball are front line, playoff caliber SP. And it makes me almost sick to my stomach that after YEARS of trying to replace Johan Santana...albeit a few years with some solid temporarily decent fill-ins...the Twins actually have THREE playoff caliber SP in place and there's all this speculation about trading AT LEAST one of them. Why?

Isn't the razing of the roster...which I get more and more as I reflect and dig and look at depth and options...enough as is? It's really not hard to look at a 2026 lineup and beyond...maybe with a temp player or two...and see tremendous potential of power and speed and better defense. And with a couple FA signings, a flier or 2 working out, and taking all the arm depth and moving it to the pen to remake it, you can see a bullpen rebuild over the next couple of seasons.

With that being said, and you don't have to squint too damn hard to see a potentially solid lineup for 2026 and beyond, why would you EVER consider tearing apart your starting staff at this point?

Let's assume the best for a moment and the Pohlads are GONE for good over the next weeks/months. The books are fairly clean, and the prospect depth is really good. 

Lopez already has a deal in place.. Ryan and Ober do not. If everything even just sorta broke right and Matthews, Festa, Sims, Abel, Bradley, and others all took off you couldn't move Ryan or Ober if they were on new deals? 

I like Ober at 3yrs and $27 and so would the Twins. I'd go 3 and $32 and front load the deal considering we are currently looking at a 2026 payroll below $100M. I'm thinking he would do that. Front loading the deals helps the future payroll, and bets against a physical breakdown. Front loading also helps in a potential trade.

I love me some Joe Ryan. And he's coming off his 1st All Star game and is a year younger than Ober. Very loose math when comparing ERA, WHIP, IP, and K per 9 has Ryan about 10-15% better in all categories. Combined with being a year younger, he's got to be worth about 20% more than Ober on an extension.

ISH

What SKEWS the proposal presented in the OP is that Ober has had an injury this season which has slowed him. Meanwhile, Ryan has had injuries the past couple of seasons that slowed him, but haven't THIS season. PLUS he has the All Star Game to bring to the table. Like it or not, a recency bias remains in contracts.

So Ryan is now worth 30% more than Ober. And being a year younger, he and his agent are looking shorter or more $.

So I'm slightly conservative about Ober at 3yrs and $32M. He's going to get another offer or two at age 34. But he's already got his life changing $.

Ryan is really smart. He wants to WIN desperately, but he also understands economics for his talent. The Twins either go HIGH for a couple of years, or they go low but for more years. And I believe he'd really like to stay here, but $ is still $.

He's either going to need 3yrs at around $15M per, or 4yrs at $18M per to make sense. Either way, he's bringing in a hell of a lot of guaranteed $, and still has the  opportunity as a 33-34yo to make another deal for several more $M.

But none of this matters until ownership changes hands.

 

 

 

[TL]

Ownership situation and the CBA being set to expire after 2026 complicates everything. It may be that the Twins are set up well to see how it plays out with few large contacts on the books. But if there is a significant work stoppage or even a canceled season, key questions include, what happens to contracts that run through 2027 (Pablo) and how is service time handled, especially for players set to be free agents after 2027 (Ryan, Ober). 

[tony&rodney]

The expiration of the CBA definitely complicates any discussion of long term contracts, especially for teams watching their money. I would be flabbergasted if the MLBPA didn't hold firm on time on control being maintained if not reduced, meaning even if the season (2027) is cancelled those who were due for free agency become free agents. I doubt there is much room for discussion on that issue.

Joe Ryan can demand some pretty high numbers if he exits this season healthy and with his current ERA through these next 7 weeks. Any extension would be well above $100M. That becomes a quandary for the Minnesota team, which makes him a prime trade commodity whether we want it or not. If Ryan can complete 2025 on a roll his value will be at peak levels. 

Would I like Ryan on the 2026 Twins? Yes.

Do I expect a trade this winter? Yes.

Do I understand anything that the front office does? No. 

[Peter]

We got tons of prospects ready to make leap!!! I’d dump Jeffers/ober/wallner/larnich. Can’t afford Ryan but that’s ok! We got Abel/bradley/festa/SWR and zebby-Pablo will be dealt this off season. It’s time for the kids to step up and take twins to World Series championship!!!!

[tony&rodney]

10 minutes ago, Peter said:

We got tons of prospects ready to make leap!!! I’d dump Jeffers/ober/wallner/larnich. Can’t afford Ryan but that’s ok! We got Abel/bradley/festa/SWR and zebby-Pablo will be dealt this off season. It’s time for the kids to step up and take twins to World Series championship!!!!

You are planning on a full rebuild. That is one plan.

[TNtwins85]

18 hours ago, TopGunn#22 said:

Interesting article.  I would offer this opinion:

With all the SP talent the Twins have added and have coming up in the minors Bailey Ober would be the LAST guy I'd consider for an extension.  I've stated a couple times in other threads that I'd be looking for Ober to build his value back up so that I could offer him (instead of Ryan) to the Red Sox for Jarren Duran or Wilyer Abreu.  Or, if Ober has mixed results in rebuilding his value, offer him to the Red Sox for minor league LH SP Payton Tolle.  The Red Sox NEED that #2 SP to slot behind Crochet (or possibly #3 to slot behind Bello if he keeps pitching so well).

Ryan and Lopez are the SP's to invest in, (we've already invested in Lopez) build around, and make the foundation for an exceptional starting rotation.  With Bradley, Abel, Festa, Matthews and SWR around and guys like Dasan Hill, Marco Raya and Conner Prielipp in the pipeline Ober is not needed (by the Twins).  But he IS needed by a team like the Red Sox.

I love Luke Keaschall.  But there is no reason to rush into extending him.  Let's give him the rest of the season, and all of 2026 to establish who he is, and where the Twins will primarily play him.  Under MLB's current system, the Twins and Red Sox are not on equal footing like, say, the Vikings and Patriots.  Roman Anthony was the #1 ranked prospect in MLB last year and to begin this year.  The Red Sox were smart to lock him up.  If Walker Jenkins ascends to #1 prospect status and dominates AA & AAA like Anthony did, then by all means...Lock Jenkins up as well.

But right now, the only extension I want to see from the Twins is JOE RYAN !!! 

I think you do whatever you can to lock up Jenkins. Either next spring depending on how he looks in spring training or the following offseason. As far as Keaschall I believe he should get a deal in spring training if it looks like he took another step forward. Ober I believe is on the Cleveland SP track where Falvey came from. If he finishes out this year strong and continues what he did last night he’s probably shopped this winter. I believe Ryan and Pablo ride out their deals as bridges to the next SP core Consisting of Hill, Abel etc. 

[Peter]

21 minutes ago, tony&rodney said:

You are planning on a full rebuild. That is one plan.

I am!!  This will be the group to bring twins another World Series championship 

[TopGunn#22]

I said that Ober would be the last guy I would offer an extension to, but let me clarify that a bit.  Essentially,  I agree with what Doc Bauer and tony&rodney are saying.  Signing Ober or Joe Ryan to extensions certainly doesn't make them untradable.  In fact, it could actually make them easier to trade with the cost certainty the acquiring team can count on.  

It's kind of like Sandy Alcantara's situation.  He's signed for something like 3 more years after this season.  The problem is that Alcantara hasn't pitched well at all.  If he had pitched like Ryan, he'd be on a different team right now and his cost would have been enormous.  Where extensions get tricky is whether a no trade clause is included.  That really ties a front office's hands.  

I maintain that the Twins CAN be legitimate contenders as soon as next season in the A.L. Central and for a Wild Card if Joe Ryan and Pablo Lopez head the rotation.  But there is no denying that Ryan would bring a HAUL back in a trade.  It's laughable reading some Red Sox centric commentary that the Twins blew it by flinching at a Wilyer Abreu, Payton Tolle and another minor leaguer for Ryan deal, essentially saying the Twins would get far less from Boston in an off season trade.  

That's not likely in my mind.  In fact, there has been angst in Boston that they came to the Twins far too late at the deadline and with far less than the Twins were demanding for Ryan.  I think Boston will pay a VERY heavy price for Ryan this off season if he continues to be their White Whale. 

I've been projecting Ober as the potential trade chip but that won't really happen if he doesn't start flashing some of his magic the remainder of the season.  Last night's game, Ober looked like Ober.  That's a very positive development.  I've always felt Ryan is the superior pitcher to Ober.  His ability to miss bats is what really separates them.  But Ober has been, and can be, a really solid #3. 

If Ober rebuilds much of his currently lost value he's worth a one-for-one for Jarren Duran.  Ober and a little something extra would certainly be worth Wilyer Abreu and Payton Tolle.  I can't remember a time when the Twins have had a deeper roster of SP. (while at the same time having almost NO bullpen). 

Ober could probably be replaced by Taj Bradley, David Festa, Mick Able, Zebby Matthews or SWR.  Any of those options might be equal to Ober, a little worse or a little better.  We have LH hitting OF stacked to the roof in the warehouse.  There will certainly be more trades to even out this roster this off season.  

 

[TNtwins85]

22 minutes ago, tony&rodney said:

You are planning on a full rebuild. That is one plan.

I love how people plan these full scale rebuilds like it’s a video game and all these prospects turn into the 90th percentile outcome and the prospects you trade for all make it to the majors. 

[tony&rodney]

1 minute ago, TNtwins85 said:

I love how people plan these full scale rebuilds like it’s a video game and all these prospects turn into the 90th percentile outcome and the prospects you trade for all make it to the majors. 

I was merely responding to Peter's apparent plan. I wasn't judging him. I just find it interesting to see what other people think. What is your plan? 

[TNtwins85]

6 minutes ago, tony&rodney said:

I was merely responding to Peter's apparent plan. I wasn't judging him. I just find it interesting to see what other people think. What is your plan? 

I wasn’t judging you either. I was simply saying how it’s funny that a lot of people present plans that are not based on reality. My plan would be a full article and would be based on rationality. Yes we could trade all of those guys for something but like you said that probably mires us in a 5 year rebuild plan when that’s obviously not what the franchise is doing or wanting to do despite what the average person thinks. Did they trade a lot of guys? Yes. Did they gut the team? No. There’s still plenty of building blocks here and from a business model Derek Falvey and the Pohlads would never “gut” the team. Why? Because that would completely dry up their income stream.

[tony&rodney]

7 minutes ago, Bigfork Twins Guy said:

Extensions...

Ryan - Yes

Ober - No

Keashall - Yes, but not until the off-season at a minimum.

Jeffers - No, only because I doubt he remains at catcher.  Have you noticed the throws to 2B this season?  He will move to DH next season or for sure by the one after IMO.

Lewis - Moot due to his agent.  If they do extend, I agree with a Buxton-like contract with a base and incentives due to his history of injuries.

These extensions should be similar to the ones offered to Polanco and Kepler.  Those seemed fair to both parties at the time and neither were negative for the team in the end.

One other note... with the upcoming CBA possibly causing an entire season to be canceled, that may entice some of these players/agents to take the extension NOW so that they are paid during the lock-out.  That also needs to be considered by the FO when deciding on the package to be offered.

 

Interesting take.

We are just throwing ideas into the wind. Did anyone have the Twins moving all those players at the deadline? So I find it mildly interesting to read all of these suggestions. I do think it is fair to criticize anyone but those with different thoughts should then propose their own ideas.

My response to the above list:

Ryan and Jeffers are ripe for being moved in trades. Obviously, the Twins need catchers and dealing Jeffers requires additions from elsewhere.

Ober and Lopez are unlikely to get dealt unless a good offer unexpectedly is brought forth or the Pohlads push the idea, which I doubt.

The Twins are unlikely to extend anyone until the ownership issue is settled. Will they sell? Remember, it was going to be completed before the 2025 season began. It will happen, maybe soon, but it might be in 2027 just as likely.

Lewis needs to get healthy or he will have trouble holding down a roster spot. He looks weak again. What is wrong? I don't know but all of us can see that his legs occasionally are unstable and he cannot run. That shouldn't play at the highest level. No team in baseball would offer him an extension. Boras would advise him to sign virtually any legitimate multi-year deal at this time. 

I need some explanation of how anyone on the current roster compares remotely to either of Polanco or Kepler. We don't have that production from anyone other than Buck who is already signed.

The CBA will be a factor in decisions, particularly for mid and below market clubs. Money talks.

[Hosken Bombo Disco]

The smart guy answer for who deserves extensions this offseason, is, of course, Derek Falvey and Rocco Baldelli. 

That said, Ryan Jeffers needs an extension. They have no one else to catch for 2026. No one. The other one I suggested was Harrison Bader. That would have to be a FA signing now. I love the speed and defense Bader brings. Given all that’s happened, shown equal offers between the Twins and another team, I think Bader chooses the other team. 

These are not young guys. But they are the best extension/sign candidates in my mind. In my opinion, the Twins simply are not set up or willing to do long term cheap extensions for young pre arbitration guys like you see other teams do.

[Whitey333]

Love Keaschall both for his playing ability and his enthusiasm.  But it seems way too early to talk extension.  The Twins have him under control for several more seasons so I say let's wait and see .  Also a potential sale of the club will probably put such extension talks on hold anyway.  Hoping they get rid of both Falvey and Baldelli before next season.  Ober should not be extended perhaps yes for Ryan.  Keep in mind that all the potential extensions mentioned here must be accepted by the player.  No guarantees that is going to happen.  I also think Lopez gets traded this off season especially if Pohlads still own the team.  If they don't sell the team I fully expect team to dump salary this off season.

[Otaknam]

Totally disagree on Lewis. He has struggled offensively all year, and is on a downward spiral if he doesn’t figure it out. His approach at the plate is hard to watch. He tries to pull everything and cannot hit a sweeper because of his pull happy approach. His struggles reminds me of Miguel Sano, who, early in his career, looked like a young Miguel Cabrera until he tried to pull everything and couldn’t hit a curveball. Lewis’ 2025 OPS is .649. The average OPS in Major League Baseball for the 2025 season is 718, so he is hurting the team offensively. Somehow they need to get him straightened out, because right now he is a below average player at a premium offensive position. That’s not sustainable.

[Otaknam]

I would wait on an extension for Keaschall. Let’s see how the rest of the season goes. When Royce Lewis came up he was electric. Right now he is a marginal big leaguer who doesn’t hit for power or with RISP. That’s not sustainable in the big leagues. Hopefully he finds his stroke again and can put behind him that “he doesn’t do slumps”, because his has been in one all year.

[DJL44]

8 hours ago, twinstalker said:

Keaschall, though, is a buy-high.  

Keaschall has zero money earned and zero track record which gives him zero leverage. There is risk in extensions for unestablished players, but that's also why the potential reward is so high. He would have to collapse to the point where they need to release him to make 8 years, $60M a bad deal for the Twins.

1 hour ago, Bigfork Twins Guy said:

Jeffers - No, only because I doubt he remains at catcher.  Have you noticed the throws to 2B this season?  He will move to DH next season or for sure by the one after IMO.

Ryan Jeffers, 1B, for 2028 would likely be as good or better than any option they currently have in the minors. Over the next 2 seasons, he's likely to be one of the top 20 catchers in MLB.

[TNtwins85]

1 hour ago, Hosken Bombo Disco said:

The smart guy answer for who deserves extensions this offseason, is, of course, Derek Falvey and Rocco Baldelli. 

That said, Ryan Jeffers needs an extension. They have no one else to catch for 2026. No one. The other one I suggested was Harrison Bader. That would have to be a FA signing now. I love the speed and defense Bader brings. Given all that’s happened, shown equal offers between the Twins and another team, I think Bader chooses the other team. 

These are not young guys. But they are the best extension/sign candidates in my mind. In my opinion, the Twins simply are not set up or willing to do long term cheap extensions for young pre arbitration guys like you see other teams do.

I would agree on Jeffers. As a guy to build around I think he is a prime candidate. Also as you pointed out we have no one else to catch and Tait is mildly far away. He would be a good candidate to split time with an aging Jeffers in 2-3years. I’d rather extend Jeffers than go shopping for a guy like Vazquez next offseason. I think they let Ryan’s natural progression play out along with Lopez. They bridge to the next crop of SP’s. As for Lewis, like other Boris clients maybe he plays it out till he’s a FA. Maybe he’s willing to take the guaranteed deal this winter the way things have gone for him. If you think Jenkins or Culpepper are legit then at least give them the deal locking them up for their prime. Keaschall… maybe this winter but they’ll have to see the next 2 months and next spring. Of course none of this probably plays out until ownership figures out what they’re doing.

[beckmt]

I have an issue giving extensions to pitchers who will be 31, 32 when their arbitration years run out.  Then you are paying for past performance and hoping they can make the adjustments with less velocity.  I don't think this team can survive with that approach.  I more like the Cleveland approach, which is to trade them when they get expensive.  This group has proven they can develop pitching,  let's go with that. 

Position is a different matter, so I can see doing  Luke Keaschall if the dollars are right.  At this pace, he could get very expensive by his 4th year, so $80 - $90 million for 7 - 8 years is reasonable.  Extend them young and don't overpay 30 year old + players.

[TNtwins85]

3 minutes ago, beckmt said:

I have an issue giving extensions to pitchers who will be 31, 32 when their arbitration years run out.  Then you are paying for past performance and hoping they can make the adjustments with less velocity.  I don't think this team can survive with that approach.  I more like the Cleveland approach, which is to trade them when they get expensive.  This group has proven they can develop pitching,  let's go with that. 

Position is a different matter, so I can see doing  Luke Keaschall if the dollars are right.  At this pace, he could get very expensive by his 4th year, so $80 - $90 million for 7 - 8 years is reasonable.  Extend them young and don't overpay 30 year old + players.

I think you’re right on point. Derek Falvey came from Cleveland. He’s operated like Cleveland as far as pitching goes. So we have to ask what Cleveland does with aging pitchers. Also, look at what they want d for the players traded. Pitching. Draft position players in the first couple rounds. Pitching in the middle rounds. Developed pitchers. Hit on a few per year. Ride them for a few years. If I look at Cleveland I’m gonna make the prediction that Ober gets shopped this off-season if he is solid the next few months. They either ride Ryan and Lopez through their contracts or shop them a year from now. By then you have a better idea of your next crop of SP’s. Rinse and repeat. They won’t extend Ryan.

[JD-TWINS]

On 8/9/2025 at 9:28 AM, DJL44 said:

Ryan Jeffers is the most obvious candidate for a multiyear contract extension. The Twins need catching. If his defense slips behind the plate they can move him to 1B. Catchers rarely get a huge payday. I think 3/$40 would get it done. That would make him one of the top 5 paid catchers at a very affordable cost. It’s Mitch Garver money.

I like Jeffers but his defense is already in the “slipped” category. Never really good.

I agree, moving him to 1B and having him stay functional as a Catcher by getting behind the plate a couple times per month would be a really good move…..,3rd Catcher always on active Roster. A 3-4 year deal makes sense as he can also DH.

Use some of the saved $$ from recent trades and sign best option FA at Catcher ……. tried this with Vazquez & it looked good on paper. May have to trade a couple guys to pry a young Catcher away from another club?

I like Ober but I can’t imagine how one throws 70% as many innings with an ERA that’s 2 runs higher than previous 2 years and he gets an 80% raise??? If they aren’t trading Lopez or Ryan, it doesn’t make sense to lock into Ober for one extra year………not with the number of mid-rotation guys currently in the system. If they aren’t trading one of the Top 2 then an extra year of affordable Ober makes sense.

If they can extend Keaschall - if he’s 75% of what he’s done so far in the future - go for it ASAP.

 

[USAFChief]

On 8/9/2025 at 1:58 PM, USAFChief said:

An extension for Ober seems...risky, to put it mildly.  And unnecessary. 

Yes on Keaschall. And soon, before he wins 2025 AL MVP.

 

 

Well ****.

Too late  now.

[bjorks]

We’ve all reached levels of delusion based on some of the ideas floated around.

Keaschall and Ryan are the only guys I’d consider to extend and one is probably out the door. The problem as some have said about Ober is if he doesn’t bounce back, who are you bidding against when he’s in his mid 30s and his numbers are similar to Kyle Hendricks? 
Extending Royce when he has proved he can play even 50% of a season? Extend Jeffers? Come on people…

the truth is if the reports the Pohlad’s have a significant cash flow problem are true and they won’t spend any more “family money” signing extensions isn’t going to happen and I doubt any potential new owner (unless they’re going to keep Falvey) is going to want the outgoing FO to spend money on guys they (or new FO) even want. 
 

[Ghost of Kirby Puckett]

On 8/9/2025 at 2:14 PM, Major League Ready said:

It's just a little early with Keaschall but you gotta love the guy.  I want to see the investment risk taken with extensions as opposed to Correa type free agents.  LA or NY can sign 6 and fail on 3.  The Twins just don't have that luxury.

I don't see it at all with Ober.  They are in a rebuild phase.  They do not need him in 2026-27 so pass on the return he would bring now makes no sense.  Take the return.  You still have the money you didn't spend on Ober.  Spend the money on a guy like Ober if you have not produced his replacement internally.   You also eliminate injury risk.  What if he needs TJ halfway through the 2027 season?

Agreed. All those arms we just grabbed, Rojas, Abel and Gallagher, are all going to get rotation opportunities next year. Along with Festa, Matthews, SWR, Lopez and Ryan. Ober is gone imo. Lopez and Ryan possibly also. I think they move Morris to the pen. Maybe Prielipp to pen. Going to be interesting. Probably an extremely young squad next year, reminiscent of 1999.