Two Extensions That Could Make Sense for the Twins Right Now

[Matthew Taylor]

Image courtesy of David Richard-Imagn Images

 

On Tuesday, the Red Sox and top outfield prospect Roman Anthony agreed to an eight-year, $130 million extension after just 47 games in the majors. The deal, which could keep Anthony in Boston through his age-30 season, is one of the most aggressive early-career commitments a team has made in recent years. It’s a signal that front offices are willing to lock in young players earlier than ever, especially if they believe they’ve found a long-term star.

The bigger takeaway for a team like the Twins is timing. When should you commit to a young player, and how soon is too soon? After a trade deadline that dramatically reduced future payroll, the Twins are in a rare position where they can think proactively. They’ve shed tens of millions in 2025 and beyond by moving on from Carlos Correa and multiple arbitration-eligible relievers. And while it’s unlikely Minnesota will redirect that savings into splashy free-agent contracts, a more logical path would be to invest some of it into locking in younger talent at club-friendly rates before the price goes up.

There are two clear candidates on the roster who fit that mold: Bailey Ober and Luke Keaschall. A third, Walker Jenkins, might seem like a natural fit, he’s a top-15 prospect, already in Double-A, and tracking for a debut next year. But Jenkins is a Scott Boras client, and Boras clients almost never sign early extensions. His philosophy is to play out the arbitration years and hit free agency at full value. That effectively removes Jenkins from consideration, at least until he’s deep into his major-league career.

Bailey Ober, on the other hand, is a much different case. After a strong showing in 2023 and 2024, Ober entered the 2025 season as one of the most reliable arms in Minnesota’s rotation. But this year has gone sideways. He currently owns a 5.38 ERA and has struggled with decreased velocity and a rising home run rate, giving up hard contact at one of the highest clips of his career. A nagging hip issue sidelined him earlier in the season, and although he’s returned to the mound, he hasn’t been able to recapture the consistency that made him so effective in previous years. For a pitcher who just turned 30 and is struggling, it’s a tough combination at a tough time.

Still, that might be exactly why now is the time for the Twins to act. Ober is making $3.55 million this year in his first year of arbitration. He’s likely to make around $6 million in 2026 and close to $10 million in 2027. That’s roughly $16 million over the next two years. If the Twins want to avoid riding the arbitration rollercoaster, and possibly buy an extra year of team control, they could offer Ober a three-year, $27 million extension that covers his two remaining arb years and his first free-agent season. A club option for 2029 around $12.5 million could give the team even more flexibility.

This would be a slightly front-loaded deal that gives Ober financial security at a vulnerable point in his career. For the Twins, it’s a low-risk play. If Ober continues to struggle, they haven’t committed long-term money. But if he regains his form from 2023–24—where he flashed SP2/SP3 potential with strong command, they could be getting two years of free-agent value at a steep discount. It’s the kind of hedge that makes sense when you’ve just cleared out a large chunk of veteran salary and are trying to stabilize your future rotation.

Then there’s Luke Keaschall. The 22-year-old infielder has fewer than 50 MLB plate appearances, but he’s already flashing the kind of tools that scream long-term contributor. A top-50 prospect coming into the season, Keaschall has certainly looked the part at the plate and on the bases in his limited time, and he looks like a strong candidate to take over second base for the long haul. If the Twins believe in the upside, this winter would be the ideal time to strike. A six- or seven-year deal worth $50 to $60 million would be in line with extensions handed out to players like Ke’Bryan Hayes and Luis Robert. The Twins would get cost control and buy out a couple of free agent years, while Keaschall would lock in meaningful earnings before ever entering arbitration.

It’s worth noting that these two extension candidates fall into very different categories. Keaschall is a young star in the making. Unproven but with real upside and long-term value. Ober is a buy-low opportunity, an arbitration pitcher with a track record but legitimate concerns. The appeal of both is different, but the logic for acting now is the same: control cost, minimize risk, and lock in value before the rest of the league catches up.

Other names might come to mind too. Joe Ryan is pitching well enough to merit extension consideration, but with just two years left before free agency and a strong platform building, he’s likely headed for a big payday the Twins probably can’t afford. Royce Lewis has elite upside but simply hasn’t stayed healthy enough or played well enough to justify a long-term deal right now. And someone like Matt Wallner might be in play as a value extension, but platoon corner outfielders rarely land multi-year deals. Kaelen Culpepper could be in the conversation this time next season, but without the prospect hype that Jenkins has, the risk for him would be too great. For now, the clearest cases remain Ober and Keaschall.

What do you think? Would you offer either of these extensions, or wait it out? Would you take a chance on someone else instead? Leave a comment and start the conversation.

 

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[DJL44]

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.

[terrydactyls]

You've presented sound reasoning for extending both Ober and Keaschall and should be considered during the off season.  With potential new ownership, it might be their opportunity to make a bold first move in Minnesota.

[DJL44]

I would be perfectly happy to see the Twins “ride the arbitration roller coaster” with Bailey Ober. What I really want to see is a bounce back in performance so he can be traded.

[CRF]

Wait...you want them to SPEND money?🤣

[tony&rodney]

This article was expected given the Roman Anthony news. The Twins are in a different world than Boston though, and other teams as well. The sale of the team will slow down any decisions related to money. 

If Bailey Ober finishes this year on a strong note, we should expect that he is traded. Nobody should be surprised if one, some, or all of Lopez, Ryan, Ober, Jeffers, Lewis, Wallner, and Larnach are moved this coming off season. 

If you were playing really well and a year or two from free agency, would you sign a team friendly deal with Minnesota?

I don't see any long term contracts being signed in the near future. The sale of the team is a factor.

[chpettit19]

I'd be doing everything I can to get Keaschall for 8/50-60. That's Ceddane Rafaela and Christian Campbell money. A 6 year deal doesn't buy out any free agent years for Keaschall. The Luis Robert deal has 2 option years on it for 20 mil a piece that would make it an 8 year, $88 million deal to get any of his free agent years (apparently Chicago intends to pay him 20 mil next year, I wouldn't). Ke'Bryan Hayes deal is 8 years, $70 million. With an option for a 9th year at 12 mil. But he signed that at the start of the 2022 season after having played in the majors for half of the 2020 season and the 2021 season. Not the same thing as what extending Keaschall would be. I think 8 years and 50 to 60 million is the contract comp for Keaschall and they should try to get that done if they can.

I don't think I'd extend Ober. They already control him into his 30s, and at his size he carries extra risk. I'd look to get him right and trade him.

[mickster]

1 hour ago, terrydactyls said:

You've presented sound reasoning for extending both Ober and Keaschall and should be considered during the off season.  With potential new ownership, it might be their opportunity to make a bold first move in Minnesota.

spend the money and extend Pablo and Ryan over Ober 

[SaberNerd]

I'm not going to commit to 3 years to a 30 yr old pitcher who hasn't been good this year and the deal only buys out one FA year.

[thelanges5]

Twins need to be sold for any of these dreams to become reality. Would love to see something in place going in to the offseason.

Ober has lost some of his appeal to me this year. Like most of the roster he has a few months here to show what he’s got for 2026. 

Keaschall would be a great candidate for a 7-8 year deal to lock him up and build around. 

Not sure how competitive they’ll be in 2026 but they’re definitely more fun to watch right now. 

[Patzky]

16 minutes ago, mickster said:

spend the money and extend Pablo and Ryan over Ober 

A different sized wallet altogether.

[Parfigliano]

Less then 50 very fantastic AB so let's extend him.  What could go wrong?  No rookie hitter has immediately lit up the league and just as quickly faded to below mediocre.  Especially no TC rookie.

[old nurse]

The 60 day IL is what will prevent the team from signing him long term. If the recent additions show talent there is no need to hang onto him.  There will be a trade next year if he shows he is healthy this September and has returned to form. That is the Cleveland and Tampa way of pitching 

[terrydactyls]

21 minutes ago, old nurse said:

The 60 day IL is what will prevent the team from signing him long term. If the recent additions show talent there is no need to hang onto him.  There will be a trade next year if he shows he is healthy this September and has returned to form. That is the Cleveland and Tampa way of pitching 

"Him"?  Are you referring to Ober?  Then I agree.

[chpettit19]

46 minutes ago, Parfigliano said:

Less then 50 very fantastic AB so let's extend him.  What could go wrong?  No rookie hitter has immediately lit up the league and just as quickly faded to below mediocre.  Especially no TC rookie.

Let's let him get established and have him get so expensive the Twins can't afford him so they have to trade him in 4 or 5 years or lose him for a comp pick in 6. What could go wrong? 

Yes, there is absolutely risk in extending guys so early. It's not a strategy that should be used constantly, but buying out a couple years of free agency and having Keaschall for 8 years instead of 6 years has it's rewards, too. The more established he gets the more expensive he gets sooner. And we all know that means the sooner he leaves. There's risk in signing him this early and there's risk in waiting to sign him. There's risk either way.

His deal should be 50 to 60 mil over 8 years. That's 6.25 to 7.5 mil per year. With where they're at in team building they can spread that out evenly over the course of the deal and have no individual season breaking the bank and hurting them seriously financially if he does completely flop. And if he turns into a star you have 8 years of a star for about 7 million. That's some pretty nice reward.

[SaberNerd]

40 minutes ago, Parfigliano said:

Less then 50 very fantastic AB so let's extend him.  What could go wrong?  No rookie hitter has immediately lit up the league and just as quickly faded to below mediocre.  Especially no TC rookie.

 An extension could turn out bad, but if he works out is extremely valuable. Doing it now significantly lowers the cost, as he isn't sure that he'll make it either. 

I want the Twins to make these moves because they are generally team friendly deals. Not sure that Keaschall would turn down a 40M guaranteed contract, even with giving up options for his peak years

[Dman]

I just can't see the Twins extending a 30 year old arm. It seems to go against the org's philosophy IMO.  They seem more likely to try and sell high or let him fall off the table.  If it's just club options for Ober I don't see that being a great incentive to sign unless he does feel he's cooked but then it is bad deal for the Twins.  I don't see an Ober deal getting done.

I like the idea of a Keaschall deal, but is he the guy you do it for?  You have Culpepper and Jenkins on the way.  Culpepper could be the more valuable player since he plays short.  Jenkins is younger and would be more in line for a deal like that as you would hate to see him on the market in his late 20's.    There was a time a deal like that made sense for Lewis and look at where things are at right now with him.  There's plenty of risk involved in early signings.

Still I could see them doing it for Keaschall.  They have loved the player he is since college.  He has great makeup and is an intense competitor.  If you think his arm is gonna be OK I'd see if he wants to do a deal. He has all the traits they need with speed, likely plus defense at 2nd, good eye at the plate, good contact skills and power.  There's a lot to like, but the Twins have never done one of these deals before so it seems unlikely to me.

[weitz41]

Keep in mind Boston can afford to extend young guys and be wrong. Not every extension is a Ronald Acuna.

Lewis with a Buxton type of contract would make a lot of sense to me. But again, Boras is his agent...so... Keushall would be my 1st choice though.

[tony&rodney]

19 minutes ago, weitz41 said:

Lewis with a Buxton type of contract would make a lot of sense to me.

I'm wondering how you arrived at this idea? More specifically, how does a long term contract make sense for Royce Lewis? I'm just curious how anyone would explain this decision.

[weitz41]

29 minutes ago, tony&rodney said:

I'm wondering how you arrived at this idea? More specifically, how does a long term contract make sense for Royce Lewis? I'm just curious how anyone would explain this decision.

Not really much different than giving someone an extension based on 47 games (Anthony) Say 2023 stats. (58 games) 308 avg, 372 OBP, 548 SLUG. Yes, I know this season's stats. The 2023 player is still there. If I'm extending someone based on talent, he the only potential star position player besides Buxton.

[tony&rodney]

1 minute ago, weitz41 said:

Not really much different than giving someone an extension based on 47 games (Anthony) Say 2023 stats. (58 games) 308 avg, 372 OBP, 548 SLUG. Yes, I know this season's stats. The 2023 player is still there. If I'm extending someone based on talent, he the only potential star position player besides Buxton.

Ok. Do you extend that same offer to Edouard Julien? Jose Miranda? Julien was arguably better than Lewis in 2023 as you know.

Many on Twins Daily have suggested that Royce Lewis is currently at such a low value, similar to Matt Wallner and Trevor Larnach, that he cannot be traded until he rebuilds some value. I have never argued that line. BTV had Royce at a 74 in November of 2023 and a 13.9 in June of 2025, not that I place any worth in the site but merely to trace a number and some support for those who say his value has sunk too low to trade. 

I'm willing to hear an argument for Lewis, but I cannot see one myself.

[weitz41]

17 minutes ago, tony&rodney said:

Ok. Do you extend that same offer to Edouard Julien? Jose Miranda? Julien was arguably better than Lewis in 2023 as you know.

Many on Twins Daily have suggested that Royce Lewis is currently at such a low value, similar to Matt Wallner and Trevor Larnach, that he cannot be traded until he rebuilds some value. I have never argued that line. BTV had Royce at a 74 in November of 2023 and a 13.9 in June of 2025, not that I place any worth in the site but merely to trace a number and some support for those who say his value has sunk too low to trade. 

I'm willing to hear an argument for Lewis, but I cannot see one myself.

Based on 2023?

Miranda: 40G .211/.263/303

Julien: 109G .263/.381/.459 (check his splits, Platoon player)

Lewis: 58G .309/.372/.548

Hands down Royce.

One of the things Falvey mentioned is they want to get more athletic. I expect one or both of Larnach/Wallner to get traded this offseason. The acquired LH outfielders make more sense if you're moving one or both of them.

Wait need to add...Except Outman..Head scratcher...

 

[USAFChief]

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

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

 

 

[Major League Ready]

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?

[SteveLV]

Extend Ober???? He has been basically replacement level this year, with an ERA over 5.  He is also 30 years old and will be 33 by the time he is a FA.  Why would the Twins do this?

Ryan, absolutely.

Jeffers, maybe, if you are convinced he can stay behind the plate.

Keaschall, let's give it a couple months, ok?

[TopGunn#22]

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 !!! 

[RonJ64]

I think we need to pump the breaks a bit on Keaschall. Yes, he looks absolutely fantastic. Yes, he's also looked very good throughout his minor league time. But, there are way too many people to name that have started out absolutely on fire. While yes, he has even set a record with his play so far, the reason you need to give this time is the league will eventually have a solid scouting report on him. He'll need to make necessary adjustments. Once this happens, we'll have a much better chance to see where he's at. He may be awesome at that point too, but until this actually happens, we just need to be patient. 

[Rod Carews Birthday]

4 hours ago, TopGunn#22 said:

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

I’m in total agreement on this.  If you are trying to build for the next window, it makes sense to have a top notch starting pitcher as a veteran left over from the previous team.  I think they would be well served by having either Pablo or Ryan stick around.   I know people are salivating over what they think he would return in trade, but I would argue that Joe Ryan is also that valuable to the Twins as the leader of the next strong rotation.  

[tony&rodney]

5 hours ago, weitz41 said:

Based on 2023?

Miranda: 40G .211/.263/303

Julien: 109G .263/.381/.459 (check his splits, Platoon player)

Lewis: 58G .309/.372/.548

Hands down Royce.

One of the things Falvey mentioned is they want to get more athletic. I expect one or both of Larnach/Wallner to get traded this offseason. The acquired LH outfielders make more sense if you're moving one or both of them.

Wait need to add...Except Outman..Head scratcher...

 

Ok. Thanks for the explanation. 

Royce - 2.4 WAR in 2023

Edouard - 2.6 WAR in 2023

I'm just not seeing it with Royce. I'm waiting for some athleticism to return. Julien is mostly done, but Lewis I'm not sold on at all.

Appreciate your response.

[ashbury]

7 hours ago, 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.

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