There are so many cracks on this Red Sox roster it’s hard to pinpoint a priority to address
, but if we keep it broad, I think we can focus on five areas of need.- Significantly more offense in left field, where the Red Sox have the second lowest OPS of any team in the American League at the position.
- A solution in the middle infield, where over over the next six weeks they’ll have some combination of Andruw Monasterio, Nick Sogard, Trevor Story, Marcelo Mayer, Isiah Kiner-Falefa, and Romy Gonzalez available, but no obvious path forward.
- Another arm in the rotation to combat the injuries, the trade of Connelly Early, and the fact that both Payton Tolle and Jake Bennett are set to blow by career highs in innings pitched.
- Multiple seventh inning options in the bullpen to slot into the same general tier as Justin Slaten and Tyron Guerrero. (Once you get beyond those two guys, it’s a real game of pick your poison to get to Garrett Whitlock and Aroldis Chapman.)
- An upgrade at catcher, because there’s just no ceiling there with Connor Wong and Carlos Narvaez.
Here’s the problem: I don’t know what I want the Red Sox to do about these holes because I don’t know the September status of Garrett Crochet, Roman Anthony, and Curtis Mead.
On the flip side, I know exactly what I really, really don’t want the Red Sox to do, and that’s take a significant stab trying to upgrade about half of these needs before
getting to the heart of September and realizing Crochet, Anthony and Mead are fully out of the picture.
To put it mildly, this is quite a pickle. I firmly believe a roster with Crochet, Anthony and Mead can make a very deep run in October, and if you look at those five areas of weakness highlighted above, those three guys fully solve two and a half of them. In other words, there are scenarios in the deck where Boston gets good news on the injury front and is only a couple of pieces away from going to the World Series as constructed right now.
Unfortunately, we have no idea if we’re living in that world. This is like being asked to bet on a poker hand without being able to look at your cards. How confident are you there’s an ace sitting under there?
Despite their absence the last three months, Garrett Crochet and Roman Anthony remain the two most important championship building blocks for this team over the next five years. They’re young, they’re locked up long-term under contract, and they each have extraordinarily high ceilings. You can build a playoff team without them, but I’m not sure you can build a championship team without them unless you’re willing to completely mortgage the future, and this is where the calculus gets really sticky.
If these guys are truly done for 2026, the Red Sox are sailing blind into a waterfall. They could royally screw themselves for the next five years by making the wrong moves in next five days. All they have to do is give up significant pieces that could help them in 2027 and beyond and not have Crochet, Anthony and Mead available down the stretch. In that scenario, you’re probably getting quickly bounced this fall, and then have much less firepower to work with in a year where Crochet and Anthony actually are vying for Cy Young and MVP awards.
Adding more fuel to this fire is the playoff format. Right now, the Red Sox find themselves seven games off the division lead, and would also need to leapfrog the Yankees to get there, who are 4.5 games ahead. This is all another way of saying that the Red Sox are probably going to end up in that Wild Card round no matter what they do.
Even if they do nothing else this deadline, I think they still get into the Wild Card round given the ridiculously bloated playoff format at this historically awful American League. They could probably even sell a piece or two and still get there — that’s how much the other middling teams in the AL suck! On the flip side, is there anything the Red Sox could realistically do at the deadline that will dramatically improve their chances of winning the division?
Even if you believe the Red Sox can become the best team in the AL by October with a healthy return of Crochet, Anthony and Mead — and I do — those guys wouldn’t enter the picture until late in the proceedings. In other words, start booking your vacation days for Tuesday, September 29th through Thursday October 1st.
Given this dynamic, I’m petrified of what the Red Sox might do over the next handful of days. The fan in me wants them to buy, but I also realize you’re pretty much building this whole thing for a three game Wild Card series where the two most important players to your franchise may or may not be available. Does that sound like a solid investment?
Perhaps the real play here is to go for the long-term options. Guys under control for multiple years so you get a shot a both the 2026 World Series and others beyond it. But then again, that’s only going to cost more, potentially further damaging your ability to build around the core going forward.
Can you see why I’m nervous yet? Why every step forward here could lead to a trap door? Let’s hope the Red Sox know a little more about the timelines of Garrett Crochet and Roman Anthony internally than they’re letting on, because if they don’t, they may cost themselves the 2027 or 2028 World Series trying to capture an unwinnable game in 2026.
Your move Craig.
