There are so many cracks on this Red Sox roster, it’s hard to pinpoint a top priority to address, but if we keep it broad I think we can focus on five general 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 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 injuries, the trade of Connelly Early, and the fact 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 contrary, 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.
In other words, I’m note sure if we’re trying to fill a pothole or the Grand Canyon. I firmly believe a roster with Crochet, Anthony and Mead can make a deep run in October — A very deep run — And if you look at those five areas of weakness highlighted above, those three guys alone fully solve at least half of them. (A healthy Crochet might even allow you to move Payton Tolle to the bullpen, where you both keep his innings down, and can use him in the 2018 Nathan Eovaldi rover role, which is an incredibly dangerous weapon if you have the depth.)
So if you’re an optimist, there’s scenarios in the deck where Boston gets long awaited good news on the injury front, and is all of a sudden 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 deadline is like being asked to bet on a poker hand without seeing your cards. How confident are you there’s an ace sitting under there?
BOSTON, MASSACHUSETTS – APRIL 07: Garrett Crochet #35 of the Boston Red Sox delivers a pitch during the first inning against the Milwaukee Brewers at Fenway Park on April 07, 2026 in Boston, Massachusetts. (Photo by Paul Rutherford/Getty Images) Getty Images
All of this uncertainty underscores a universal, unescapable reality: 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, 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.
This may sound harsh, and I know the club has been the hottest team in baseball over the last month, but winning games in July and winning games in October are two entirely different beasts. Power, pitching and poise matter orders of magnitude more when the leaves start to change color, and in doing so, they tend to push hustle, grit, and vibes into the background. You still need those latter items in the dish, but they can’t be the main ingredient the way they are now.
This is where the calculus gets really sticky. If Crochet, Anthony and Mead are truly done for 2026, the Red Sox are sailing blind into a waterfall. It’s just a matter of how sharp the rocks are at the bottom. The club could royally screw itself for the next five years simply by making the wrong move 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 are actually 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 held by the Rays, 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. This includes if they do nothing.
When you combine the ridiculously bloated playoff format and this historically awful American League, they’d have to suffer an outright collapse to miss the dance now that they’ve got the 15-game winning streak in the bank.
But 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. There’s no runway where you can use those guys to chase down the Yankees and Rays. All of their 2026 upside is tied to the postseason at this point.
In other words, start booking your vacation days for Tuesday, September 29th through Thursday October 1st, because the Red Sox are probably going to be playing do or die baseball over those 72 hours.
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 can’t overlook the fact they’re pretty much building this whole thing for a three game Wild Card series where the two most important franchise players 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 publicly, because if they don’t and they’re flying as blind as we are, they may cost themselves the 2027 or 2028 World Series while chasing a ghost in 2026.
