What the Brewers Can Teach the Twins About Trading Joe Ryan

[Cody Christie]

Image courtesy of © John E. Sokolowski-Imagn Images

The word "seller" carries a negative connotation around the trade deadline. It signals surrender, rebuilding, and punting on the current season. That's why it's understandable that the Twins have shown little interest in waving the white flag while they remain in the American League playoff race. But what if there was another way to approach the deadline?

Over the last several years, the Milwaukee Brewers have built one of baseball's most sustainable organizations by refusing to let emotion dictate difficult roster decisions. They haven't traded stars because they were rebuilding. They've traded them because they understood the value of moving elite players before their trade value began to decline.

The Twins may soon face that same crossroads with Joe Ryan. Ryan has developed into one of the American League's best starting pitchers. Through 104 1/3 innings this season, the 30-year-old owns a 2.85 ERA with 122 strikeouts. He's pitching like a legitimate front-line starter, and has earned a second straight All-Star nod. He's also under club control through next season, giving any acquiring team two postseason runs to make the most of his upside.

That combination is incredibly valuable. It also means Ryan's value may never be higher. If Minnesota wants to maximize its long-term championship window, it should at least consider following Milwaukee's blueprint.

The Brewers Never Wait Too Long

Small-market teams rarely win by keeping everyone together forever. Instead, they maximize every asset before free agency forces difficult decisions. Milwaukee has mastered that philosophy.

Rather than allowing stars to walk away for draft-pick compensation, the Brewers have consistently identified the moment when a player's value peaked and turned those players into multiple years of affordable talent. That strategy hasn't pushed Milwaukee into rebuilding. Instead, it has helped the Brewers remain one of baseball's most consistent contenders.

Here's a look at how Milwaukee has handled similar decisions with some of its biggest arms. One detail immediately stands out: only one of these trades happened at the deadline. The others came during the offseason, when teams were willing to pay a premium for a full season of control.

Corbin Burnes
Trade Date: February 2024

After the 2023 season, Milwaukee traded Burnes with one year of club control remaining. Rather than settling for draft-pick compensation, the Brewers landed two players capable of contributing immediately in DL Hall and Joey Ortiz—and they picked up a competitive-balance pick from Baltimore to bolster their 2024 class.

Hall has transitioned into a bullpen role and taken a significant step forward this season, lowering his ERA to 2.03 while increasing his strikeout rate from 17.4% to 25.4%. Ortiz produced 2.8 WAR with a 102 OPS+ during his first season in Milwaukee before taking a step back offensively. Neither player has become a superstar, but Milwaukee turned one remaining season of Burnes into two controllable major leaguers while staying in contention. (Blake Burke, whom they took with that draft pick and on whom they also saved about $500,000 in bonus pool money to spend elsewhere, has an .846 OPS in his pro career and is likely to reach Triple-A this summer.)

Josh Hader
Trade Date: August 2022

Perhaps no Brewers trade was more controversial than dealing Josh Hader in the middle of a division race. At the time, fans questioned why Milwaukee would move arguably baseball's best closer while trying to reach the postseason.

The Brewers looked beyond the current standings. Milwaukee acquired Robert Gasser, Taylor Rogers, Dinelson Lamet, and Esteury Ruiz. Gasser has already become a capable big-league starter, despite a significant setback in the form of Tommy John surgery in 2024. Rogers added a lefty to the bullpen for the stretch run, and Ruiz was later included in the three-team trade that brought William Contreras to Milwaukee. In fact, he was all the Crew gave up to land Contreras, who has now made two All-Star teams for them.

Hader had limited club control remaining, and relievers rarely carry more value than as elite closers with a chance to anchor a playoff bullpen for multiple seasons. Milwaukee capitalized before that value began to decline. This one comes closest to being a cautionary tale, because that was the only time since 2017 that the Brewers have missed the postseason, and the front office was blamed for that, based on the vibes of a midseason trade of such magnitude. However, in the medium and long term, it looks like a brilliant maneuver.

Devin Williams
Trade Date: December 2024

Milwaukee repeated the process with Devin Williams. Rather than extending an expensive closer into his 30s, the Brewers again moved one of baseball's premier relievers while his value remained exceptionally high.

The Brewers received Nestor Cortes and infielder Caleb Durbin for Williams in the 2024-25 offseason. Cortes's injuries limited his impact before he was moved at the following trade deadline, while Durbin later became part of another multi-player deal that brought Shane Drohan, David Hamilton, and Kyle Harrison to Milwaukee. Once again, the Brewers turned one valuable reliever into multiple controllable assets, and got production even in the meantime.

Freddy Peralta
Trade Date: January 2026

Freddy Peralta represents the same type of decision the Twins may soon face with Ryan. After years of trade speculation, Milwaukee finally dealt Peralta to the Mets for top prospect Jett Williams and right-hander Brandon Sproat. Williams remains one of baseball's top prospects despite an uneven season at Triple-A, while Sproat immediately stepped into Milwaukee's major-league rotation.

Ryan fits a similar profile. As was true with Peralta, an acquiring club wouldn't simply be renting him for two months. Ryan would provide a postseason run this year and another full season of control in 2027. That dramatically increases the asking price.

Why Ryan Could Bring Even More

Ryan's combination of production, durability, and contract status makes him one of the most valuable pitchers who could realistically become available. He's not owed a massive contract, and he's pitching like a legitimate ace. That's exactly the type of arm contenders are willing to overpay to acquire. With the extra half-year of control baked in, he would have to fetch Minnesota more than what Burnes or Peralta got for Milwaukee.

The Twins already possess one of baseball's strongest farm systems after last year's deadline additions. Trading Ryan wouldn't signal the end of their competitive window—it could extend it. Imagine adding multiple top-100 prospects, upper-level pitching depth, and another high-upside position player to an organization that already features Walker Jenkins, Kaelen Culpepper, Emmanuel Rodriguez, Eduardo Tait, and several other premium young talents.

The Timing Matters

One lesson stands out from Milwaukee's recent history: only Hader was traded during the season. Burnes and Williams were moved during the offseason, while Peralta remained with the Brewers through another postseason run before they eventually cashed in. That's an important distinction for Minnesota.

The Twins don't have to make this decision before the trade deadline. If they believe this team can reach the postseason, Ryan can remain atop the rotation through October before the front office revisits trade discussions this winter. In fact, that could be the better path. Teams often pay a premium for a pitcher with a full season of control, rather than just two months, giving Minnesota the opportunity to compete now while preserving Ryan's long-term trade value. The Brewers have repeatedly shown that patience can be just as valuable as urgency.

It's About Extending the Window

The Brewers have shown there is a difference between selling and managing a championship window. They've remained annual contenders because they consistently make emotionally difficult decisions before circumstances force them into weaker ones.

The Twins don't have to trade Joe Ryan. If they believe they can sign him to a long-term extension, keeping him is the obvious choice. But if an extension isn't realistic, waiting until the final months of his contract could dramatically reduce his value. At that point, acquiring teams would receive only a few months of control, instead of another full season, shrinking both the number of interested clubs and the quality of offers.

Trading Ryan would undoubtedly be unpopular. It would also require tremendous confidence in Minnesota's scouting and player development departments. That's exactly the type of move successful small-market organizations make—though, we ought to note, the Twins are a small-market team more in self-image and by default than in fact. 

Milwaukee has demonstrated that moving elite pitchers before free agency isn't waving the white flag—it's investing in sustained success. The Twins may not consider themselves sellers this summer, and they probably shouldn't. However, if another organization is willing to offer the type of franchise-altering package Milwaukee has repeatedly secured for its stars, Minnesota owes it to itself to listen.

Whether that decision comes in a few weeks or this winter, the Brewers have already provided the blueprint. Sometimes the hardest trade isn't the one that closes a championship window—it's the one that keeps it open for years to come.

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Can Minnesota follow Milwaukee’s blueprint? Leave a comment and start the discussion.

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[Whitey333]

Good timely article!  I totally agree to trade him while his value is high.  The o ly thing i question is that in mentioning the talent the Twins prospects, none of Kulpepper, Jenkins, Rodriguez, Tait have yet to prove they can be major league players.  In fact at this point they are more suspects than prospects.  But we are pulling for them. Go Twins.

[thelanges5]

Who is going to pitch if they trade Joe now? They barely have 5 starters with him in the mix. 

[mikelink45]

There is another aspect that is not in the essay - the Brewers seem to really know how to develop their pitching.  They trade well, but then they fill the void with really good arms.  We have not shown that.  Prielipp is out with a blister and has been okay, Festa is no where to be seen on the IL, Matthews has done okay, but not exceptional, Rojas has a good arm but is not the quality SP a contender needs.  Ober is not ready to be the Ace.  Raya is already on the IL. Abel is on the IL, Bradley is the next in line for the Ace position.  And Lopez?  I hardly remember when he pitched last - will he return as an Ace?

The article says we have a good farm system - its time to see it produce at MLB level.  Keaschall is struggling to regain his rookie production, Lee is an average player, Wallner is gone, Lewis is still suspect with his 219 BA, Martin is back to below average and we have our prospects on the IL or just waiting for a chance.

I agree he has to be traded - he will leave as a free agent, but so far I do not have the trust in our system that we will show the Brewers' shrewdness. 

[rv78]

And the Brewers have zero Championships using this strategy. Trading away your best players pushes the window down the road. It doesn't open the window. The Twins won their only 2 Championships by being buyers, not sellers. They adding to the talent they had. Using the same strategy the Brewers are using will only work if you change it at the right time and ADD the talent you need to push you over the top. Otherwise all you do is push, push, push and your opportunity is into the next decade. I'm running out of decades. 1987 and 1991 have been a long time ago. 

[Mike Sixel]

2 minutes ago, mikelink45 said:

There is another aspect that is not in the essay - the Brewers seem to really know how to develop their pitching.  They trade well, but then they fill the void with really good arms.  We have not shown that.  Prielipp is out with a blister and has been okay, Festa is no where to be seen on the IL, Matthews has done okay, but not exceptional, Rojas has a good arm but is not the quality SP a contender needs.  Ober is not ready to be the Ace.  Raya is already on the IL. Abel is on the IL, Bradley is the next in line for the Ace position.  And Lopez?  I hardly remember when he pitched last - will he return as an Ace?

The article says we have a good farm system - its time to see it produce at MLB level.  Keaschall is struggling to regain his rookie production, Lee is an average player, Wallner is gone, Lewis is still suspect with his 219 BA, Martin is back to below average and we have our prospects on the IL or just waiting for a chance.

I agree he has to be traded - he will leave as a free agent, but so far I do not have the trust in our system that we will show the Brewers' shrewdness. 

Lee has been a top ten 3b since moving there.

[Mike Sixel]

1 minute ago, rv78 said:

And the Brewers have zero Championships using this strategy. Trading away your best players pushes the window down the road. It doesn't open the window. The Twins won their only 2 Championships by being buyers, not sellers. They adding to the talent they had. Using the same strategy the Brewers are using will only work if you change it at the right time and ADD the talent you need to push you over the top. Otherwise all you do is push, push, push and your opportunity is into the next decade. I'm running out of decades. 1987 and 1991 have been a long time ago. 

Agreed, but now is not the time to add ...

[JD-TWINS]

So, the article points out that the two Starters traded were with one year of control left and moved in the off-season.

The in-season, deadline trades were for two front line closers.

I realize the details are just to show a “Brewer strategy” BUT I wait until after the season to consider trading Joe as there will be more stability in negotiations and potentially, more interested Teams.

[SteveLV]

The choice is simple:  Either extend Ryan or explore his trade value.

If the trade value is good/great, pull the trigger.

I would prefer they extend him, but this FO hasn't even approached Ryan for that according to all reports. Sad, but true.

[rv78]

23 minutes ago, Mike Sixel said:

Agreed, but now is not the time to add ...

Never said it was. It isn't a given that it is the right time to sell either.

[bean5302]

26 minutes ago, Mike Sixel said:

Lee has been a top ten 3b since moving there.

By what metric? He's been below average to lousy by the data driven ones.

[bean5302]

The question of a Joe Ryan trade has a few facets, but the biggest question is whether this team's competitive window is open with the roster we have? I'd say probably not. There are too many holes.

 

[old nurse]

What the article shows is that when you trade your star players at best you get back complementary players and fodder for more trades.  If you use the fodder well, you can get another star player. Every now and then you will get a good player in a non premium position like Durbin

[Brock Beauchamp]

To quote a Cubs fan I follow;:

”The Brewers have traded Freddy Peralta. Now they have 12 years of control of two new Freddy Peraltas.”

Of course, this only works if you’re elite at targeting and development, which the Brewers are and the Twins are not. 

[Glorybound]

The 26 Twins don’t have enough bullpen to win close games down the stretch. The time to trade Ryan is now when his value is the greatest. If they still had Varland and a healthy Banda then I might think differently. At this point it’s the hand they have been dealt time to recognize it for what it is.

[Nashvilletwin]

Here is what everyone is forgetting: a salary cap and floor is coming.  Make no mistake about it.  It will be here no later than 2028.  The floor will be at least $175MM (maybe there is a ramp up period over a year or two).

The Twins are going to need to spend money.  A lot of it.

This is why they will hold off trading Ryan now (and Buxton for that matter).  They will hold onto Ryan this year, play out their unexpected competitive season, and then decide if  Ryan is the right guy to extend or trade over the off-season.

The Twins are going to be chock full of young, cheap, up and coming position players and pitchers in ‘27 and ‘28.  They will need to augment that roster with a handful of higher priced players - Ryan just still might be one of them.  If they trade him now, the Twins will lose that option on Ryan (as he will surely be extended by the acquirer).  He stays.  

[chpettit19]

Burnes is actually an example of why I'd trade him before the deadline. Teams aren't "willing to pay a premium for a full season of control" by trading for a guy during the offseason if it's just 1 season of control. Teams pay for control. 2 playoff runs will get you more value than 1 full season. Joe Ryan is worth more now than he will be in the offseason. The Brewers didn't hold onto Burnes to "get a premium for a full season of control," they held him because they were 57-50 at the deadline. Not below .500 like the Twins have been since April 22.

Trade Joe Ryan. And Ryan Jeffers.

[chpettit19]

57 minutes ago, SteveLV said:

The choice is simple:  Either extend Ryan or explore his trade value.

If the trade value is good/great, pull the trigger.

I would prefer they extend him, but this FO hasn't even approached Ryan for that according to all reports. Sad, but true.

Joe Ryan signed a new deal this last offseason that included an option for next year. Not sure what reports you're reading, but they had to talk about his future with the team to do that. Joe Ryan has been very open for nearly his entire MLB career that he wants to hit the market and thinks the arbitration system is stupid.

The Twins are clearly not a super well-run team, but not having extensions for players doesn't automatically mean they haven't discussed it. As it turns out, players have the ability to say "no."

[Peter]

Ryan isn’t going anywhere!!! Just stop with this!!! Enough of the negativity!!! Facebook is horrible for that!! Twins are in hunt for playoffs and division championship!!! 

[hitterscount]

Our frugal spending will not change, so the question becomes when to trade Ryan. As long as the team is in contention for a postseason bid I would hold on to him and make the move this winter. But the bottom line is I wouldn’t pony up the cash that would be needed to extend him…. he’s earned it, but you can’t have that type of money he’s going to get tied to one player.

[tony&rodney]

The Brewers are cruising this year but if they are to roll in the playoffs they will need to add or risk having their winning record as the highlight of their year. It is a good mark and one to be proud of but at some point the Brewers will need to have the pieces to get back to the World Series. Is that going to be in a few years with Lara and Made?

Meanwhile the Twins are left with top prospects often injured and failing to take the next step. Injuries are an unfortunate reality of athletics. Where are the Twins in their plans to be competitive? If one makes a list of needs to boost the Minnesota roster, one thing seems to stand out for me. The club is in need of a legitimate star player. In my opinion the recent steps to move a number of players around defensively have decreased the holes in the infield and outfield. The offense has been scoring runs at a fair clip too. The 2026 Twins are much more interesting than the last couple of years. Still, there are clear holes, with the bullpen being an obvious issue. Can a couple of prospects fill the void?

The decision with Joe Ryan is a difficult one. He is going to get a big contract if he gets to free agency and will require a chunk of the payroll to sign to an extension. I see what the Rays, Guardians, and Brewers have done with their players but find their success as noteworthy but not necessarily the model that the Twins can follow. In some cases it was the follow -up transactions that created value for the Brewers (Contreras and Harrison). Is that something that can be replicated? My take on trading Joe Ryan has not changed at all since last July. If the Twins can manage to acquire a major prospect (Franklin Arias, Leodalis, De Vries, Jesus Made types), do it. It may be possible to find a deal for multiple players but I haven't seen anything I'm finding decent. The next option is to sign Joe Ryan. Third, the team waits until the offseason. A pile of pretty good maybe's doesn't hold any interest for me. 

[strumdatjag]

Of course, the Twins accept an overpayment for Ryan 

But FIRST concentrate on moving one of our three catchers.  I’d like to see Jeffers signed longterm with Caratini traded to a contender desperate for a catcher (but keeping Caratini and trading Jeffers should be explored as well).  
The Twins have too many left-handed hitting outfielders.  Try to trade some of that glut for one or two major league arms and more minor league pitching prospects.  
Use the deadline to start to rebalance the roster and the minor league system. 

[hitterscount]

1 hour ago, rv78 said:

And the Brewers have zero Championships using this strategy. Trading away your best players pushes the window down the road. It doesn't open the window. The Twins won their only 2 Championships by being buyers, not sellers. They adding to the talent they had. Using the same strategy the Brewers are using will only work if you change it at the right time and ADD the talent you need to push you over the top. Otherwise all you do is push, push, push and your opportunity is into the next decade. I'm running out of decades. 1987 and 1991 have been a long time ago. 

My counter to your point is Milwaukee will draw over three million this season. Most games Ive watched this season there aren’t 10,000 people in the park. Winning matters, consistency matters we aren’t there.

[Rod Carews Birthday]

As always, whether to pull the trigger depends on the return.  The only way I trade Ryan at the deadline is if I think the return is a big overpay.  It could happen, but only if there is some sort of bidding war for him — a bidding war (possibly with more participants) that might just as easily occur over the winter.  

Yes.  He could be injured and ruin his value.  Yes, it is unlikely that we will re-sign him. If you say that with every good player, then you effectively shorten your team control over your best players by one or two years.   However, Joe Ryan is the obvious anchor on the pitching staff, and for all the fawning over Lopez (who I like A LOT), probably has been for the past couple of years.  If we trade him at the deadline, we are absolutely flushing away what has been a pretty fun season with the team doing a little bit of overachieving.  IF Tom Pohlad is serious about building a winner, now is not a great time to take a step backward.  

As for other players, again, it all depends on return.  But I would definitely explore trading Larnach, Jeffers, and Martin.  We have replacements on hand in Roden, Caratini/Jackson, and Keaschall, and if we can acquire pieces (ahem. . . relief pitching) that will help us down the stretch and beyond, we would be putting our efforts into areas of higher priority for now and building for next year.

[chpettit19]

Call Atlanta and tell them the talk starts with Caminiti and Hartman and we'll go from there.

[LA Vikes Fan]

While I agree that the Twins either need to extend Ryan or trade him, there is no urgency to make that decision at the 2026 trade deadline. The urgency domes in the offseason. History tells us that teams overpay for relievers at the deadline by giving up quality prospects for average guys. That is not equally true of starting pitching. I think you actually get your best deal in the offseason for starters, not at the deadline, because you can t get MLB proven talent at the deadline. You only get unproven prospects at the deadline. They are simply not as valuable as controllable proven talent. 

There's also a business and team imperative that has to be considered here.  Ownership is trying to reestablish trust with the fan base. There also trying to create team camaraderie, something Shelton is doing a great job with. Both of those things would be almost irretrievably broken by trading Joe Ryan at the deadline in a year when the Twins have an actual chance to sneak into the playoffs. Sure, if the they do sneak in they probably only last one round and if they get lucky and win the first round, they probably get blown out by the big boys in the second round. Still, a year like that can really help with the fan base and help in recruiting free agents to come and improve the team in the future. Those are real and important considerations and both of them point strongly away from trading Ryan at the deadline.

Ryan stays in 2026. You try to sign in the off-season and, if you can't, you trade him before spring training.

[mnfireman]

The Brewers traded these pitchers before they hit 30, except Williams, he turned 30 late in late September of '24....that's what they can teach the Twins: develop them early and trade them while they are still young, but getting expensive.

[Fatbat]

As much as we would love to keep Ryan long term and make deep runs into the playoffs for the next 5 years with him, realistically, we need to cash him out now for multiple younger stars that will help bring us closer to a world series run for the next 5-8 years.  We need to upgrade many positions so we need a bigger pool of developmental talent. I hope T. Pohlad understands that fact. 
 

[The Great Hambino]

4 minutes ago, LA Vikes Fan said:

While I agree that the Twins either need to extend Ryan or trade him, there is no urgency to make that decision at the 2026 trade deadline. The urgency domes in the offseason. History tells us that teams overpay for relievers at the deadline by giving up quality prospects for average guys. That is not equally true of starting pitching. I think you actually get your best deal in the offseason for starters, not at the deadline, because you can t get MLB proven talent at the deadline. You only get unproven prospects at the deadline. They are simply not as valuable as controllable proven talent. 

There's also a business and team imperative that has to be considered here.  Ownership is trying to reestablish trust with the fan base. There also trying to create team camaraderie, something Shelton is doing a great job with. Both of those things would be almost irretrievably broken by trading Joe Ryan at the deadline in a year when the Twins have an actual chance to sneak into the playoffs. Sure, if the they do sneak in they probably only last one round and if they get lucky and win the first round, they probably get blown out by the big boys in the second round. Still, a year like that can really help with the fan base and help in recruiting free agents to come and improve the team in the future. Those are real and important considerations and both of them point strongly away from trading Ryan at the deadline.

Ryan stays in 2026. You try to sign in the off-season and, if you can't, you trade him before spring training.

I generally agree with the overall point that the best time to trade away relievers is at the deadline while the best time to trade away starters can be in the offseason under the right circumstances due to supply and demand factors that I'll save for another day and another rant. 

But this is not a typical offseason.  No one is giving up anything of real value for someone with one year of control when they aren't sure what they're actually getting for that control while the season is still up in the air.  If you're thinking you can just move Ryan in the offseason, you're making a massive gamble that they'll be avoiding a lockout (they will not be avoiding a lockout).  If that doesn't happen, what are teams giving up when what they're getting is a mystery box?

Too many unknowns to think you can maximize Ryan's value in the offseason.  So trade him this deadline or actually commit to competing while you still have him. 

I suppose one angle they could be taking is there could be a post-CBA environment where they'll be in a position to be able to offer him more than any other team in free agency if something similar to the NBA's Larry Bird rights materializes (plus some combo of revenue sharing and a floor that makes increased spending both more realistic and necessary), and they can more realistically view him as part of the core of the next few years.  But assuming that is coming is also a huge gamble.

 

[tony&rodney]

5 minutes ago, Fatbat said:

As much as we would love to keep Ryan long term and make deep runs into the playoffs for the next 5 years with him, realistically, we need to cash him out now for multiple younger stars that will help bring us closer to a world series run for the next 5-8 years.  We need to upgrade many positions so we need a bigger pool of developmental talent. I hope T. Pohlad understands that fact. 
 

Many people can agree with the "multiple young star" return idea. However .... Who are those young stars? In the last year I have proposed trades for Franklin Arias (last July) and Leodalis De Vries or Max Clark (last winter). Those were never likely to occur. I'm not seeing any proposals that pique my interest thus far.

At this time, the Twins may want to see where the team is on August 2 before making a decision. There may be ongoing discussions about a contract extension as well. I'm keeping an open mind. 

There has been quite a bit of discussion about the strength of the farm system, especially last year. It might be time to push some players forward. Kaelen Culpepper and Walker Jenkins could fill positions. The starting pitching has navigated through some challenges but is still managing to give the club solid starts. The main issue remains the bullpen. The biggest question is whether Ryan Jeffers and a few prospects can be traded for good relief pitchers. The speculation keeps building but the deadline could be quiet too.