Last summer, the Red Sox made a bold bid to bolster the rotation and acquire Joe Ryan from the Minnesota Twins. But of course, as we now know, they didn’t land their man.
What we didn’t know at the time – or at least didn’t know in detail – is that the Twins balked at an offer including both Payton Tolle and Franklin Arias. On one hand, most Red Sox fans are thrilled that puppy didn’t go through, and for good reason. But you know what? After this week’s deadline that included Adley Rutschman coming
in and Marcelo Mayer going out, I’m still kind of fascinated by that potential blockbuster that fell apart the last trip around the sun.
When you couple the 2025 Joe Ryan deadline deal that didn’t happen with the moves this week that did, a pretty clear and wild pattern emerges: Craig Breslow is stunningly aggressive. Over the last year and a half, this trend has consistently manifested itself in two clear ways: One, he’s not afraid to put a haul of prospects on the table to get a player he covets. And two, if you’re not marching in tune of his vision for club, you’re going to be shown the exit, and quickly.
Let’s run through six examples here (three from each category) to underscore the point.
Since December of 2024, Craig Breslow:
- Traded Kyle Teel, Chase Meidroth, Braden Montgomery and Wikelman Gonzalez to the White Sox for Garrett Crochet.
- Offered to trade Payton Tolle and Franklin Arias to the Twins for Joe Ryan.
- Traded Anthony Eyanson, Kyson Witherspoon, Enddy Azocar and Carlos Narvaez to the Orioles for Adley Rutschman.
That’s eight top ten prospects (albeit not at the same time) that Breslow’s been willing to part with to acquire established major league pieces.
Secondly, we have the Breslow moves that purged certain guys from the organization. All three of these occurred in just the last 15 months:
- The Rafael Devers trade to the Giants last year.
- The Alex Cora firing in April.
- The Marcelo Mayer trade to San Francisco.
All three of those guys were involved in some level of friction within the organization, and when the front office saw their chance, they parted ways.
This is the complete opposite of how Chaim Bloom ran the show. Now, to be fair, he was in accumulation mode while he presided over the farm, ut stop and ask yourself this: How many of those six moves would Chaim Bloom have made, and how many of those six moves would Dave Dombrowski have made? Regardless of your exact answer, it’s hard to imagine any scenario where Bloom’s number is higher.
The biggest difference between now and ten years ago is the Red Sox aren’t going to lead baseball in payroll anytime soon like they did at the end of the Dombrowski era. But that has nothing to do with Breslow; he’s operating inside the budget granted to him by ownership. What he’s proven in the last 20 months is he’s willing to spend the currency sitting in front of him, and spend it big.
Ideally, there will be more of a balance in the spending of prospects and dollars when everything shakes out, and who knows, maybe that will come in the form of an Adley Rutschman extension soon. But it’s been quite a ride to watch Craig Breslow get this aggressive.
Along those lines, I wonder how much this is sustainable. One of the worst things about the last great core of Red Sox baseball is how little the group accomplished outside of 2018. They followed up that 108-win, World Series season by missing the playoffs in 2019, and then having that unmitigated disaster during the Covid season of 2020. The details of how that fell apart so fast are a topic for another day, but the discussion as to how to make sure that doesn’t happen again is very present.
So with that, I want to bring another factor that’s somewhat specific to Breslow’s situation and may also be driving his vision.
All the prize pieces Breslow’s acquired in these big deals have been under team control for at least two cracks at a World Series. Crochet was under control for two years (and then they extended him). Erik Miller, whom they got for Mayer, is under team control through the end of 2029. Curtis Mead is here through 2030. And Joe Ryan would have been here for three shots at a World Series. Even Adley Rutschman will be in Boston for at least two more Septembers, and if he ends up signing an extension, it really solidifies Breslow’s long-term vision and trade type.
The broader point here is the guys Breslow goes after are not rentals. He wants multiple bites at the apple, and that’s a big reason why he’s been willing to pay a high price in terms of prospects. Perhaps the thinking there is that while long-term, expensive free agent contracts often turn sour on the backend, deals that include big payments in prospect hauls leave you time to rebuild the farm as long as what you get in return is under team control for multiple years.
It’s a great idea on paper, but let’s see how it plays out in reality.
Lastly, bringing it all back to the Joe Ryan deal that didn’t go through a year ago, not having Joe Ryan in that Wild Card series again the Yankees absolutely kneecapped them. Even if you’re thanking whatever God you pray to that Payton Tolle and Franklin Arias are still here, it’s okay to admit that Brayan Bello starting Game 2 in New York completely derailed the Sox in that series. He faced eleven batters, failed to get five of them out, got bailed out by an Anthony Volpe double play, and put the Sox on a track where they had to use six relievers and ultimately stretch the high leverage part of the pen too thin.
Knowing this, I wonder if Breslow and company are still stinging from that experience, because they’ve certainly responded like it. In the last nine months they’ve aggressively added to the rotation, started their trade deadline moves a week early with Curtis Mead (even though that blew up in their face), and then offered another huge package to land Adley Rutschman and ensure they weren’t left without their man again.
Maybe he’s a nerd, maybe he’s a stiff, maybe he’s still learning on the job, and maybe he still reminds you of Chaim Bloom — but make no mistake, Breslow is acting a whole lot more like the guy who was here ten years ago than the guy who was here five years ago. He just doesn’t have the same sized checkbook at his disposal. Now we’ll see how long he can make this run last.
