Why the Minnesota Twins Should Sign Bailey Ober to a Contract Extension Now

[Cody Christie]

Since his debut, Bailey Ober has emerged as a starting rotation mainstay for the Twins. He’s starting to get more expensive in the arbitration process. Is now the time to lock him up for the long term?

Image courtesy of David Richard-USA TODAY Sports

The Minnesota Twins face a crucial offseason, filled with decisions about shaping the future of their rotation. Bailey Ober is one name that stands out as a long-term investment candidate. With three years of team control remaining, now is the perfect time for the Twins to lock up Ober to a contract extension, ensuring stability in their starting rotation for years to come. Here’s why extending Ober makes sense from both the team’s perspective and the player's.  

Ober’s Track Record of Success
Ober has quietly developed into one of the most dependable arms in the Twins’ rotation. Since his MLB debut in 2021, Ober has consistently demonstrated a rare combination of control and efficiency. Across 88 big-league starts, he has posted a 3.76 ERA (112 ERA+) with a 1.07 WHIP and 25.6% strikeout rate. 

In 2024, Ober took a significant leap forward, proving he’s more than just a mid-rotation starter. Over 178 2/3 innings, he posted a 3.98 ERA, 1.00 WHIP, and career-high 191 strikeouts. His increased reliance on a devastating changeup paired with his deceptive fastball has helped him keep hitters off-balance, leading to one of the lowest hard-hit rates among American League starters (83rd percentile). His xSLG on the changeup dropped from .346 in 2023 to .263 last season. It was a huge step forward for Ober’s development. 

The Case for an Extension
With three years of arbitration eligibility remaining, the Twins can capitalize on Ober’s current team control to craft a team-friendly deal. Extending Ober not only buys out his arbitration years, but potentially secures his services into his early free-agent seasons.

For context, look at comparable pitchers who signed extensions with similar service time.

• Logan Webb (San Francisco Giants): Entering 2023, Webb agreed to a five-year, $90-million extension with the Giants. This deal covers his remaining arbitration years and extends into his free-agent eligibility, ensuring his presence in the Giants' rotation through at least the 2028 season.
• Cristian Javier (Houston Astros): On Feb. 10, 2023, the Astros signed Javier to a five-year, $64-million extension. This contract encompasses his arbitration years and includes additional seasons, reflecting the team's commitment to him as a key rotation member. Unfortunately, he underwent Tommy John surgery last season.
• Mitch Keller (Pittsburgh Pirates): Keller and the Pirates agreed to a five-year, $77-million extension on Feb. 22, 2024. He was coming off an All-Star season, but was two years younger than Ober at the time of the deal. This extension covers his arbitration period and secures his role with the team into his early free-agent years.

For Ober, a deal in the range of five years and $65-$85 million, with a possible team option for a sixth year, could provide security for both sides. He will likely earn more than $4 million this season and $18-21 million over the two thereafter. On the high end, he will already earn $25 million in arbitration. From the team’s perspective, it’s a gamble worth taking. Pitchers are inherently risky investments, but Ober’s increased workload and performance last season might make him worth the risk.  

The Long-Term Rotation Outlook
Extending Ober also aligns with the Twins' long-term rotation strategy. The team has promising young arms like Simeon Woods Richardson, David Festa, and Zebby Matthews on the horizon, but prospects come with uncertainty. Ober provides a proven presence in the rotation, complementing Pablo López and Joe Ryan to form a reliable trio.  

By securing Ober now, the Twins would avoid the potential escalation of arbitration costs and the risk of losing him to free agency at a time when reliable starters are fetching exorbitant prices. Additionally, locking up Ober allows the front office to focus on other areas of need, knowing that a key piece of the rotation is already in place.  

A Win-Win Scenario
For Ober, the security of a long-term deal offers peace of mind. As a late bloomer who didn’t receive a substantial signing bonus when drafted in the 12th round, a guaranteed multi-million-dollar contract provides life-changing financial stability.  

For the Twins, it’s a move that reflects foresight and commitment to maintaining a competitive window. In an era where pitching is the backbone of any postseason contender, extending Ober is a step toward ensuring the Twins keep their winning window open as long as possible.

Ober has proven he belongs in the Twins' future plans. With his unique skill set, consistent production, and the ability to provide innings at a high level, the time is right to reward him with a contract extension. Doing so would send a clear message: the Minnesota Twins are serious about building a sustainable winner.  

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Should the Twins attempt to extend Ober? How much would the team offer? Leave a COMMENT and start the discussion. 

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[rdehring]

Could not agree more.  But do the Twins?  Or Ober?

[Twins GFP]

Agree this would be a good time for this discussion.  You have to wonder about how a pending sale impacts the Twins signing long-term contracts at the moment.

[chpettit19]

If the payroll situation were different, I'd agree this would be the time to buy out a year or 2 of free agency. But with the current payroll situation and team sale possibility this doesn't feel like the time they're going to be looking to lock themselves in to more future deals. I'd actually wager it's more likely Ober is traded before his last arb year than he's extended before his last arb year unless a new owner takes over.

[nicksaviking]

I wouldn't say no, but I'll say the same thing when this came up with Kyle Gibson: based on his age, Ober will already be in Minnesota about exactly as long as I'd like him to be here. As much as I love Ober, and have no interest in trading him, I'm not sure I want to lock in a starting pitcher for his age 32+ seasons unless he's an all-time great.

[Doctor Gast]

I like the idea of trading away players we don't need so we can extend the players we do. Not trading players we do need to sign players we don't. I hope we have money to extend maybe a Ober or Lewis while still have intact a very competitive team.

[hitterscount]

1 hour ago, chpettit19 said:

If the payroll situation were different, I'd agree this would be the time to buy out a year or 2 of free agency. But with the current payroll situation and team sale possibility this doesn't feel like the time they're going to be looking to lock themselves in to more future deals. I'd actually wager it's more likely Ober is traded before his last arb year than he's extended before his last arb year unless a new owner takes over.

The payroll situation is a self imposed limit put in place by a multi billionaire who has zero interest in fielding a serious team. Locking up Ober makes sense so therefore it will not happen. 

[Blyleven2011]

Ober has been a blessing for the pitching staff , each year he has improved his game and should be considered part of the future  ...

Maybe not extend this offseason but it might be wise to extend him next offseason  with the current scenarios of the twins team future  ...

[Rod Carews Birthday]

This is not a bad idea at all, but I personally would wait one more year.  By then he will hopefully have an even more consistent track record AND you will have a better picture of what more of the young pitching looks like.  Maybe Festa and Matthews (and others) look awesome, and then he becomes a trade candidate.  Maybe they are lousy and we desperately need to hang onto Ober.  When it comes to extensions, next year becomes the big year.  There are so many players on this team who currently have three years of control it's a little scary.  We won't be able to keep them all, but hopefully some will be displaced by younger players coming through the minors. 

[bean5302]

Unless Ober is considered to be an upper rotation starter, and clearly the better option compared to Joe Ryan, the answer is no. In my opinion, Ober carries a great deal of decline risk, and he's a #4 type starter. Extending guys like Ober is admitting the front office doesn't have anything to replace him. You don't buyout/extend #4 starters. You can just as easily replace them in free agency for about the same cost.

Logan Webb was an ace. Javier was coming off an a25 ace-like season. Ober is not comparable.

Keller is comparable to Ober, but Keller had already finished his arb 1 season before agreeing to the extension so the Pirates only had 2 years of team control. This would be like a 6 year contract (a29-a34) for Ober. A structure like 6 yrs and $70MM probably would work, but why would the Twins do it?

While fans seem to want their teams to extend every single good player they have, in reality, Ober should just be blocking cheaper variants of himself.

[Coach]

Bailey and his agent thanks you for all the stats, boosting his value vs. others.

[old nurse]

Christian Javier would be the reason not to sign an extension to pitchers. After signing his ERA went up to 4.58. The next year is TJ. Now this year will be the rehab and regain year. 

[tony&rodney]

The Twins have 3 more years of control over Lopez, Stewart, Ober, Jax, Ryan, Duran, and Larnach. All of these guys are good but none are superstars. Until the team is in a stable position it seems likely that the Twins will roll year to year with their current guys. 

[Linus]

I really like Ober but I would not extend him. You have him at arb salaries until age 32 which is a perfect time to trade him get a prospect and let someone else pay for his decline years.

[gman]

I like Ober and think he is great in the rotation, BUT, I can't see them signing any long term deals with anyone this winter. If a new owner shows up, they can make those decisions. If there is no new owner, Ober will be traded or leave in 3.

[TwinsDr2021]

11 hours ago, Bigfork Twins Guy said:

I thought the Kepler/Polanco deals worked out well for the team.  If we could replicate that great.  No Dobnak deal though.  That one did not work out so well.

Kepler and Polanco are gone and both are still younger than the age the Twins have Ober controlled though.

The idea of the Twins extending players they have controlled though age 30 or beyond, is crazy talk IMO.

Also unless the Twins are grossly going to over pay, why in the world would Ober or do this?

[TwinsDr2021]

14 hours ago, bean5302 said:

Unless Ober is considered to be an upper rotation starter, and clearly the better option compared to Joe Ryan, the answer is no. In my opinion, Ober carries a great deal of decline risk, and he's a #4 type starter. Extending guys like Ober is admitting the front office doesn't have anything to replace him. You don't buyout/extend #4 starters. You can just as easily replace them in free agency for about the same cost.

Logan Webb was an ace. Javier was coming off an a25 ace-like season. Ober is not comparable.

Keller is comparable to Ober, but Keller had already finished his arb 1 season before agreeing to the extension so the Pirates only had 2 years of team control. This would be like a 6 year contract (a29-a34) for Ober. A structure like 6 yrs and $70MM probably would work, but why would the Twins do it?

While fans seem to want their teams to extend every single good player they have, in reality, Ober should just be blocking cheaper variants of himself.

Kind of like Cody forgot to do some research.

Javier was extended though age 30, Keller though age 32, and Webb though 31.

The twins already have Ober though age 31.

The writers on this site Love to talk about the age of prospects being X number of years younger in the minors, but love to ignore age in other discussions.

The only Twins pitcher that the Twins should talk about extending is SWR (because of age)

[DJL44]

12 hours ago, Linus said:

I really like Ober but I would not extend him. You have him at arb salaries until age 32 which is a perfect time to trade him get a prospect and let someone else pay for his decline years.

If he's really doing well until that age and the team is doing well enough to keep him, you slap the qualifying offer on him and get a draft pick back like they did with Sonny Gray

[LambchoP]

It'd be a great idea to lock up Ober and Ryan, IF we had the payroll space, but obviously we don't. Plus, I'd wait another year to see if Ober and Ryan are for real top of rotation main stays, and we'd have a better idea of what we've got in Festa, SWR and Mathews. How good the three of them project to be will probably determine how badly we need to lock up Ober and Ryan.

[tony&rodney]

Several people have mentioned that the uncertain ownership financial situation precludes signing large long term contracts at this point and others have responded with a thumbs down. 

The thumbs down has always been mysterious to me, particularly when a comment is vanilla. Perhaps a short response would make more sense .... in this case something as simple as .... "No, I believe management will sign long term contracts".

[Seansy]

The #1 reason Ober won't/shouldn't get an extension is the 1 thing not mentioned in this article: Ober is already 29 years old with 3 years of team control remaining.

Any extension will be for his age 32 and up seasons.

Unless the Twins get a steal of a deal that pays him way less than he is projected to make they will go year to year with him until he is traded or becomes a FA.

You could make the same case to extend Joe Ryan since he is a year younger than Bailey and also has 3 years of control left but for the same reasons he is unlikely to be extended.

For contrast, Pablo is only a few months older than Joe and he is also signed for exactly 3 more years.