Why didn’t the Red Sox close the Joe Ryan deal?

Photo by Brace Hemmelgarn/Minnesota Twins/Getty Images

For a brief moment during the minutes leading up to Thursday’s MLB trade deadline

buzzer, it appeared as though everybody atop the Red Sox organization had done their jobs. Craig Breslow had landed a bonafide No. 2 starter, John Henry was willing to pay for that starter, and the major news outlets were beginning to report the blockbuster one by one.

First, it was Fox Sport MLB:

Then moments later, it was Yahoo Sports:

And finally, Spotrac joined in:

But as is increasingly the case in our hollow, vapid

world, it all turned out to be fake. All of these major, verified, gold check marked news organizations got it wrong. Unsurprisingly, there was no explanation as to how that happened, what sources on the inside may have led them astray, or the details of the conversations occurring between Boston and Minnesota outlining how close the two sides actually got.

All we know is the two sides got close enough to a deal that multiple outlets were reporting it done, and then when all the dust settled, it didn’t get done. This is failure of journalism, this is failure of the Red Sox front office, and most of all — if I’m allowed to speculate — it’s a failure of Red Sox ownership.

Before we start surmising and connecting the dots that led to disaster, we need to pause on that brief juncture of jubilation. If the Red Sox really had landed Joe Ryan as reported by Fox Sports and Yahoo, this is what the top of the Red Sox rotation was going to look like for every October series between now and at least 2027:

Photo by Maddie Malhotra/Boston Red Sox/Getty Images

Oy!

Look at that picture and allow yourself to understand how dramatically the acquisition of Ryan would have changed the American League landscape. With Ryan still years away from free agency and Garrett Crochet already locked up, this instantly makes the Red Sox a brutal out for any team who happened to run into them in a short series. You wouldn’t even need to stretch very far to argue the Sox as favorites to win the pennant in 2025.

If you really want to delve into what the moment felt like as the raw information was pouring out, there was a trade deadline livestream event yesterday with Jared Carrabis and the crews of Baseball is Dead and Section 10, and if you click here at the 4 hour and 55 minute mark, you can ride the roller coaster of emotions with them.

It’s like a walk-off home run drift foul.

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Now that we’ve established the whirlwind of the moment, we need to zoom out and refocus our attention on what I believe may have been the biggest failure of all: John Henry and his unwillingness to spend enough money to make the Red Sox legitimate championship contenders.

Less than two months ago, the Red Sox sent Rafael Devers across the country and offloaded a quarter of a billion dollars from their books. While shocking in the moment, the true litmus test for that deal was always going to be how the Devers money was reinvested. Well, less than two months later, we now know it’s not going to be reinvested into the 2025 Red Sox.

If John Henry was actually still serious about winning championships, he would have instructed his front office to use his financial might to land a big fish and dramatically improve the roster for a postseason series. But as reported in a few different corners, that wasn’t the case.

Here’s Tyler Milliken breaking down one report by Chris Cotillo citing “money is a factor in negotiations with the Red Sox”:

One executive told @ChrisCotillo that money is a factor in negotiations with the Red Sox.

“Boston has $9-10 million to go before crunching up against the next CBT threshold of $261 million. That would seem to be hard to get to. But one executive who has had talks with the Red… pic.twitter.com/3Iw3G9N0WN

— Tyler Milliken (@tylermilliken_) July 31, 2025

Less than an hour later, the always excellent Red Sox Payroll quote tweeted Tyler’s post and went into even more detail on where the guardrails lined up:

Anything spent over $261M (2nd CBT line) would incur a 42.5% tax.

If they end up with a $270M payroll, they'd pay $6.88M in taxes.

If they end up with a $280M payroll, they'd pay $10.08M in taxes.

It's not my money; it both is and isn't a lot. Depends on the club. https://t.co/DuA5FXb9ox

— Red Sox Payroll (@redsoxpayroll) July 31, 2025

I can’t tell you how repulsive I find this garbage! If you’re the owner of the Boston Red Sox and you think those thresholds are a lot, you shouldn’t be the owner of the Boston Red Sox!

Being frugal while rebuilding is one thing, but when you hit the upward trajectory of the success cycle and you have the stack of chips Henry has, it should immediately be followed by an array of aggressive moves that actually get completed each winter and summer deadline for several consecutive seasons.

Specifically, big market organizations should be buying horrible contracts from bad teams to lower the prospect cost in any deal. This way, you can both improve your odds of winning a championship in any given year while also preserving the farm system for future seasons. The ability to absorb these types of deals instead of having to pay with prospects is one of the biggest advantages big market teams have because it allows them to push windows open earlier and then extend them later in the cycle. With the amount of excess cash Henry has on the sidelines right now, it’s also exactly what they should be doing.

But instead, the Red Sox 2025 payroll seems poised to tumble as far down the list of MLB team spending as it ever has during John Henry’s ownership.

Photo by Clive Mason/Getty Images

Potentially related to the lack of Red Sox spending — and this is pure speculation — is what happened yesterday with Carlos Correa. The Twins needed to unload that contract and were looking for somebody to take as much of it as possible, and just after 4:00pm, they found that somebody in the Houston Astros.

The Athletic reported the Twins sent Carlos Correa back to his old team for Matt Mikulski, a 26-year pitcher in High-A. Essentially, they traded him for nothing. More importantly however is the note in that story confirming the Twins agreed to eat $30 million of the remaining $96 million on the Correa contract. Furthermore, this deal came together quickly and didn’t seem to truly gain momentum until yesterday morning when reports of Houston third baseman Isaac Paredes potentially being done for the season began to surface.

So here’s my question: How much was Carlos Correa discussed in laying the framework for a potential Joe Ryan to the Red Sox deal before Houston swooped in at 4:00pm on Thursday? There’s no way the entirety of the failed flirting session between Minnesota and Boston happened in the last two hours before the deadline. These teams were exchanging ideas, working on a framework, thought there might a be deal to get done, and then just didn’t get it across the finish line.

You know what I think? The Red Sox were originally going to eat part of Carlos Correa’s contact in the framework of a deal with the Twins, but they were only willing to eat up to the guardrails laid out by Red Sox Payroll in the tweet above. Craig Breslow and company were weighing their options based on the market and the parameters set by John Henry, and in final few hours before the clock struck midnight (or 6:00pm in this case), the market shifted.

Once Correa went off the board, the Twins’ asking price went way, WAY UP! Suddenly, they had all the leverage because now they not only could ask for more prospect capital with the Red Sox not kicking in money, but also because they lost their biggest reason for doing the deal in the first place (getting rid of Correa). So now, the Twins could ask for the moon, the stars, the sun, and the entire Boston farm because the 6:00pm deadline wasn’t all the important to them. They can wait until the winter and still move Joe Ryan.

But for the Red Sox, they were caught flat-footed and totally unprepared to deal with the shifting winds. Other names flew off the board around the league, the clock ticked down, and the following direct quote from Breslow later that evening began to play out:

“For whatever reason, we weren’t able to line up.”

As far as I’m concerned, “for whatever reason” is carrying Mount Everest on its back. The entire story from yesterday, whatever the details may be, are embedded in those three words. All the rest of their clone bot business speak broken promises are about as empty as the Padres farm system.

Breslow failed, Henry put him in a position to fail, and to top it all off, the major news outlets failed. If you want more speculation, my guess is that some source leaked from the Red Sox side thinking they were going to get a last minute deal done with the Twins based on the framework discussed before Correa went to Houston, and that just wasn’t going to happen in the new reality. It would also make sense why the Twins didn’t think they were close from their end.

In any case, the Red Sox ended the day not making a single trade with a team that had a record below .500. They were caught looking for value in a market where it didn’t exist. Despite Craig Breslow’s strength of actually being pretty darn excellent at finding value and not making underwater deals, he is completely incapable of knowing when you have to pay extra just to get to the next checkpoint. Maybe you don’t want to spend $5.00 per gallon on gas, but guess what? The next station isn’t for 150 miles and it’s on the other side of a mountain pass, so if you don’t fill up now and make a deal for bad value, you’re going to go the way of the Donner Party when the weather turns cold in October.

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One last thing because I’m really, really annoyed. Does anybody else despise these virtual press conferences as much as I do after massive team news? The Red Sox did this after both the Devers trade in June and again after the trade deadline wrap up here.

I just find it so weaselly as it allows them to bounce between questions in a way that you never get close to the bone of the issue. If you want to do both a virtual conference and an in person one to accommodate different people that’s fine, but this is something that needs to be done live, in front of actual people in a physical setting. Otherwise, it’s about as useless as those reports from Fox Sports and Yahoo.

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