The decline from a glorious peak is one of the most unsettling things in life, and sadly, the modern world is full of them. The deterioration of local town squares as small businesses shut down, the enfeeblement of loved ones as they age, the morning after a good buzz, and the uneasiness of daily life in a decaying empire are just some of the obstacles most of us have to navigate through on a rather relentless basis.
But fear not! We have sports, the ultimate distraction that somehow not only allows
us to temporarily escape the crushing reality, but also connects us all simultaneously. At their best, sports, and in particular baseball, provide such an uplifting and communal experience that they can force the surrounding hellscape to fade into the background, even if only for a few hours. (I can attest firsthand that this magnificent dynamic is one of the reasons I’m alive today.)
But unfortunately, the Red Sox experience of late — as in the entire first half of this decade — has largely been one resembling the greater decline and decay. Not exclusively in the on-field product, which has actually gotten much better over the last 12 months and should continue to be solid over the next couple of years, but in the way the Red Sox operate as an entity.
Perhaps nowhere has this unsettling existence been on display more grotesquely than over the past week in Orlando at the Winter Meetings, where ownership and the front office allowed both Kyle Schwarber and Pete Alonso —by far the two biggest power bats on the free agent market in an offseason in which the Sox are desperate for power — to end up in the Mid Atlantic instead of New England. In a vacuum, that’s not the end of the world. But against the progressively problematic backdrop of needs and empty promises, it’s a font of exasperation.
Here’s my gripe: Last year, Trevor Story led the Red Sox in home runs with just 25. The Yankees, in comparison, had five guys hit more than 25 home runs in 2025, and a sixth in Giancarlo Stanton who hit 24 of them in just 77 games. Going back over the last 33 years, there have only been three seasons in which the Red Sox failed to to have at least one guy hit more than 25 home runs. One was the Covid year, so that doesn’t count, and the other two were in 2012 and 2017.
Do you remember how the Red Sox responded the last two times they had a power deficiency like this in their lineup?
- After 2012, they spent in free agency by re-signing David Ortiz (who only played in 90 games in 2012 and thus only had 23 home runs that year), and also signed Mike Napoli. Those two guys then went on to lead the Red Sox in homes runs in 2013 on the way to a World Series title.
- After 2017, the Red Sox spent in free agency by signing J.D. Martinez to a five-year, nine figure contract. He went on to lead the 2018 Red Sox in home runs with 43, and once again the Red Sox went on to win the World Series.
The formula was simple: Needs naturally appeared on the roster each offseason, and then the team would use their enormous financial resources, largely supplied by the equally enormous Red Sox fanbase, to address those needs on the free agent market. But since 2019, the machine has stopped functioning — or at least the part of the machine where fans get a sizable free agent return on their investment has stopped functioning.
This winter, there’s a clear need for a power bat in the Red Sox lineup, and not only did they not get either of the two guys on the free agent market who were far and away the best candidates to address that need, but they got blatantly outbid by the Baltimore Orioles in both years and dollars.
Following this news, I think NC Hellrazors beautifully summed up fan frustration in the comment section if our Over The Monster Open Thread thread from yesterday. Here’s the post:
Anyone else remember the days of waking up in the morning, turning on ESPN to see if (the Sox) made an overnight deal/signing and getting excited to see something awesome happened? It was like Christmas. Man, so long ago.
Once again, we’re living through the decline from a glorious peak. The Red Sox have more than enough resources to get aggressive in free agency. They simply choose not to do it because “it’s expensive to have (good) baseball players” according to John Henry. And hey, how else are billionaire sports owners supposed to make money without exploiting the passion of their fanbase?
Disgusting and infuriating!
But do you know what I personally find almost equally disgusting and infuriating? The way the Red Sox continue to feed everybody a line of bull about how they’re prepared to operate like the 2004-2018 Red Sox when they very clearly have zero intention of swimming at the deep end of the pool when it comes to top end free agent targets anymore. It’s been so long since they actually delivered on this front that they now have zero of the 35 largest contracts in the sport on their books. (Garrett Crochet’s $170 million deal comes in at No. 36 on the list in case you’re wondering.)
All of this brings us to what happened with Will Flemming this week. Being the play-by-play voice on WEEI, Flemming is tapped into the Red Sox messaging, and like many others who are also tapped into the Red Sox messaging, I believe he’s being fed a big steaming pile of horse manure.
Here’s how Flemming relayed what he’s been hearing to starving Sox fans on Twitter, and how it proceeded to play out in three acts:
I can’t speak for everybody, but I’m pretty sure that when we get to Friday afternoon and those 72 hours are up, I’m not going to be smiling. Because what I really want from the Red Sox is for them to pair their formidable financial muscle with their blossoming farm system and put the fear of God into the rest of the American League. This is not a guns vs. butter situation. They can do both!
This is true even if you subscribe to the idea of pulling back during lean times and rebuild years and then ramping back up once again as a strong foundation solidifies in place. At some point, you have to shoot for the moon and go for it. And honestly, the fact we’re specifically not seeing action at this stage of the game is where much of my personal anger comes from on this topic. If you’re not going to invest in top-shelf free agents at this point in the team’s success cycle, when are you going to invest in them? Without that, the Red Sox as we once knew them are officially dead.
But their ghost is still very much alive, because every winter, like clockwork, we get these annual fraudulent declarations and intimations passed down from on high. My favorite came at the end of the 2023 season when Tom Werner told us the team was going “Full Throttle” that winter, and we all had to conclude at different points in the proceedings that it was complete bogus. Then, after they backtracked, Craig Breslow tried to do some damage control in early 2024 by suggesting it would make more sense to truly invest in additions after the young players arrived and were making an impact. See if you can get through this round of gobbledygook:
But I think the reality is that it’s going to require a step forward from the young position players. It’s going to require the build-out of a talent pipeline of arms that we can acquire, we draft, and we can develop internally.
And it’s going to require aggressive player development in the minor leagues and the major leagues so guys that we think are the next wave — Mayer and Anthony and Teel, that group — are not just big leaguers but impact big leaguers.
Well, the kids are here and I still don’t see any big free agent splashes. But do you know what we did see when the kids arrived? Rafael Devers and his $300 million contract being shipped out the door. In the moment, we were led to believe it was predominantly about the player needing to be moved out of the clubhouse and not about the value of the contract. But if that were the case, don’t you think it might have been a good idea to invest, oh say about half the money saved on that “malcontent” on one of the power bats that just went off the board in free agency? If it really wasn’t about the money, those funds would have been reinvested and used to replenish the power lost in the lineup during Devers’ departure.
Instead, we’re getting the latest tsunami of deception, distortion, dishonesty and deceit from Red Sox higher-ups who pass down disinformation in an attempt to defend the existence of a reality they no longer care to preserve.
The bottom line is winning the World Series is not the main objective for them in 2026. It comes second to winning the gathering labor war with the players next December, and they’re willing to make people who respect them look like fools to pretend that’s not the case.
Unfortunately for everybody involved, the evidence just keeps piling up. Remember this gem from last year when the greatest need was an ace?
The only reason this didn’t end in disaster like things have in previous winters is because the Red Sox got to a point where they could turn around and trade for a high-end starter from their deep farm system. And you know what? That’s fantastic when it’s paired with real investment on free agents. Heck, the Red Sox are even likely to still make a pretty big impact trade this winter, and I mostly trust Breslow to do that because he’s gotten pretty darn good at these.
But sadly, that still leaves us with a missing piece. The Red Sox are only collecting value players, and if nothing of value is available, they move on and don’t get anything good. Now, some might say this is a brilliant strategy because if you do it for long enough, you’ll eventually compile the most value-filled roster top to bottom anywhere in the sport. But here’s the problem, I don’t think that approach wins championships. I’d love for the Red Sox to prove me wrong, but running an MLB team isn’t just akin to managing a portfolio. It also has aspects of the following imperfect real world scenario sprinkled in:
Suppose you’re taking a cross-country road trip and you’re goal is to get there in the most economic way possible. So you start your journey on the east coast and you decide you’re going to be really good about only filling up at the cheapest gas stations possible. It works great for a while, but then you start to encounter more and more remote stretches of highway with larger gaps between towns and more treacherous terrain. You skip by places to fill up because the gas there wasn’t a good value, and then eventually you get to the point where you have less than a quarter tank left and there’s 146 miles to the next station on the other side of the mountain pass. You’re options are either to pay for what you need, even if it’s not good value, or chance the success of the entire trip because you were too cheap to pay for it.
That’s where we’re with the Red Sox. It doesn’t matter how well Roman Anthony can drive the bus if you run out of gas in a blizzard in the middle of Mooseball, Montana. In baseball, sometimes you have to deviate from the initial plan and go after guys who are good and not cheap to address a need, and if you don’t like that, you’re in the wrong industry! The key is finding the right balance between maximizing the value on the roster and when to cross the line. Or as Andrew Friedman so succinctly put it a decade ago:
“If you’re always rational about every free agent, you will finish third on every free agent.”
Oh, and if you’re not willing to do what it takes to finish first on any of the big free agents, stop feeding good people in the industry steaming piles of bull. Either that or you go on Twitter and face the toxic (but entirely justified) masses yourself. I’d be willing to pay Fenway Park ticket prices to witness those fireworks!
