This might be the scariest seven day stretch of the season because the Red Sox must put their cards on the table and reveal when they’re actually going to go for it.
Here comes the biggest litmus test for Craig Breslow’s front office to date.
The kids have arrived, the team is on the upswing, and the pitching staff has both a legitimate ace up front and a shutdown closer in the back. In short, the Boston Red Sox have the foundation to be a great team, but they’re also incomplete if they want to win a World Series in 2025. The biggest missing piece? A No. 2 starter, and it’s not even close.
Personally, I like to refer to legitimate No. 2 starters as face card pitchers. Just like when playing a good hand of cards, a serious baseball team will lead with an ace when all the chips are on the table. However, what often separates the contenders from the pretenders is what happens on that second trick. Are you throwing a member of the royal family down, or are you playing an eight of clubs? Are you sending Joe Ryan to the mound for Game 2 behind Garrett Crochet, or are you letting Lucas Giolito take the ball, give up four home runs, and hoping to to pull out a miracle in a hostile environment like you did last night? (Sure, it’s possible to win that second way, but if we’re strictly talking odds — and we all know how much this front office loves numbers — it’s probably not a great idea.)
In this specific moment, I see four solid reasons the Sox need to go out and get a face card pitcher in the next seven days. Let’s go through them:
1) It’s the most obvious glaring hole on the team.
In Garrett Crochet, the Red Sox have the best starter they’ve had in a long, long time. Behind him, it’s just a bunch of wild jokers. Between Lucas Giolito being a turbulent mystery from start to start, Walker Buehler struggling to resurrect his career, Brayan Bello maybe making a leap (I’m not quite ready to take the cheese there), Patrick Sandoval maybe coming back at some point, and Dick Fitts being yo-yoed around as an afterthought, the Red Sox have more than enough bottom half of the rotation arms.
What they truly need to be a force in October is one more dependable flame thrower to fill the gap. If they go out and grab a No. 3 guy (or to keep with the metaphor, a ten of diamonds) it’s a complete waste of resources on this specific team. The staff already includes a bunch of arms who comprise of a middle of the road straight, which you go no points for in this game. If Breslow is going to part with pieces to upgrade the rotation, the only efficient way to do it is to get somebody who is significantly better than the bottom of the rotation guy they’re going to displace.
2) The postseason format favors teams with top heavy rotations.
I’ve made no secret about my disdain for the current MLB postseason format. I even proposed a pretty simple way to dramatically improve it last week if you want to read that here.
But we’re not doing that today. Instead, we’re focusing on how the Red Sox can best take advantage of the broken format in front of them — and oh boy would they be a tricky team to deal with if they got into one of these short series with Crochet and a second bullet in the chamber.
Set Number: X164734 TK1
Here’s baseball’s dirty little secret in 2025: Winning the World Series has never had less overlap with a team being the best in the sport. Historically, you had to be really, really good just to make the postseason; and that, for the most part, weeded out the mediocrity. However, not only do twelve teams make the postseason in this ridiculously bloated playoff structure, but the first half of October is comprised of two tiny series and a million off days. The result is that teams with a top heavy rotation have an enormous advantage.
In a five game series, teams can throw each of their two best guys twice (and if they happen to get the series with an extra stupid off-day between Game 1 and Game 2 to accommodate the network needs of having the two leagues off-sequence, they can do it with both top guys on normal rest). What a stupid system!
Meanwhile, in the hideous best-of-three Wild Card round, the series could be over before you even get to the third starter if the top two guys do their job. That would then be followed by multiple off-days because again, this MLB playoff format is dumb!
In any case, the underlying point here is that all the depth stuff that matters and helps separate better teams over a 162-game season ends up being completely meaningless in the first two weeks of October. Those first two rounds where the field is cut from twelve teams to four in the blink of an eye is complete mayhem, and for the best teams it’s actually the trickiest obstacle to negotiate in chasing a title.
We’re conditioned to think the difficultly will enhance, and that each round will get harder because that’s how it’s supposed to work in life. In college, you escalate towards a final exam. In video games, you build towards a final boss. And in other major American sports like the NFL and NBA, the early rounds are populated with fraudulent teams who have zero chance of winning a title need to be slaughtered before the real show starts. But in baseball? It’s exactly the opposite!
These short series inject total chaos into a sport that already has chaos naturally built into its DNA. It’s totally unnecessary, but it’s also what we’ve got. Therefore, the most underrated key to winning the World Series is to build a squad specifically conditioned to morph into a top heavy demon designed to get by these disorderly rounds. More often than not, you’re going to get to the LCS in this format and say, “there’s no way these are the four best teams in the sport.”
You just have to build a team to be one of them.
3) The American League Sucks!
Not only are the first two rounds of the playoff mayhem, but who exactly are you worried about turning into a juggernaut this fall? This is the worst I’ve ever seen the top of the AL in my lifetime, and shame on the Red Sox if they don’t try to take advantage of it.
Maybe the timing would be a little better, or the math a little more efficient to wait and go for it another year, but it’s hard to believe you’re going to get a board this wide open again. While you can control when you peak, you can’t control the tides, the sun, the wind or the environment around you. The Red Sox could easily have the best team in baseball in 2028, go for it, win 105 games, and lose in the anarchy of the first round to the stupid Rays because that’s how baseball works.
When the door is open, and it is right now, drive a truck through it!
Photo by David Berding/Getty Images
4) Money
Money talks, and last month the Red Sox offloaded about a quarter of a billion dollars from their books when they sent Rafael Devers across the country. This combined with stagnant Sox payroll figures in recent years while inflation and FSG profits have run rampant speaks volumes. This franchise has the ability to take on a bad contract in a deal for a strong starting pitcher to lessen the prospect cost. If they don’t so that, people are going to be rightfully infuriated! And personally, if that Devers money is not reinvested back into the team on the field in some fashion by next March, I’m going to turn into somebody this ownership really isn’t going to like.
Perhaps the big move comes this winter in a free agent contract? Or maybe via extensions to Alex Bregman, Roman Anthony and Marcelo Mayer? But it could also come in part by just agreeing to take on Carlos Correa’s contract from the Twins in a quest to pry Joe Ryan out of the land of 10,000 lakes and ten trillion mosquitoes. Correa is owed about $100 million over the next three years ($32.83 million in 2026, $31.83 million in 2027, and $31.33 million in 2028 followed by a bunch of team options), and is clearly a negative asset on Minnesota’s books.
Regardless of how the Red Sox negotiate the next seven days, they’ll be picking a direction on when exactly they want to truly go for it with the most exciting core of young players they’ve had in years. If they play their cards right and drop a king on the table, it might be the beginning of a new royal reign that lasts through the end of the decade. If they’re not going to do that, they might as well fold and walk away from the table for a few months because they’re still more serious about winning in 2026 than they are 2025.