If you frequent Over The Monster, you may already know I absolutely detest MLB’s bloated current playoff format. Way too many teams get in, you can win your division and end up not making the LDS, and the September spotlight strays away from the spectacular squads who spent the first 130 games proving themselves to alternatively focus on flawed teams trying muster 83 wins and grab the final Wild Card spot. Nasty, nasty stuff!
But I’m not here to complain about the overarching gripes I have with the system
today, or at least not as much as I usually do. Instead, I want to dive into another bizarre byproduct of this increasingly swollen playoff structure, and how the Red Sox may be positioning themselves to take advantage of it. Specially, I want to underscore how baseball in 2026 is more about small sample size, readiness, rest, and randomness than it’s ever been in its history.
You’d never know it by the way we talk about baseball now — WAR, wOBA, wRC+, BABIP, xFIP, and every other stat that needs a large sample size to normalize dominates the conversation — but in terms of being one of the last teams standing in the middle of October, being good at the right time is increasingly more effective than being good a majority of the time.
So before we join the Red Sox and go to meet the baseball devil, we have to stop and take a moment to marvel at the irony. In an age where we can calculate everything to the point that 99% of the audience will stop caring about the details in the quest to create the best team on paper, having the best team on paper over 162 games has actually never mattered less.
We can track exit velocities and spin rates, we can track arm angles and run production, we can track defensive metrics and zone ratings, and then we can add it all up, throw it in a formula that would make an MIT grad blush, and determine who the best of the best are in a league of large sample samples. That’s all great, except for the fact that having the best team isn’t necessarily how you get to the World Series anymore.
Instead, it’s more about having the hottest and healthiest players over a very specific window. It’s a road the sport’s been trending down for the better part of the last 30 years, but thanks to the gluttonous owners and their dopey third Wild Card that was specifically spawned to salivate their insatiable search for more money, we’ve arrived in baseball hell.
For most of MLB history, the most direct (and really only) path to get near the World Series was to win as many regular season games as possible. But now, the path to and through the playoffs involves this awkward two step process we really haven’t ironed out yet.
1) Don’t suck! (Just be a handful of games over .500 in the regular season and you’re probably getting in the playoffs.)
2) Play your best baseball for somewhere between three and eight games spread over a twelve day stretch when the regular season ends.
I don’t think we talk anywhere near enough about how ridiculous that second bullet is in determining a champion. Once you’ve got a team on paper that can win 85 or more games (a pretty low bar), surviving that klutzy corner of the calendar where the schedule resembles anything but a typical baseball stretch for a fortnight becomes orders of magnitude more important for your chances of winning a World Series than adding regular season wins to you total. It sucks, but it’s very much the reality.
In terms of strategy, being one of the twelve best teams in the sport over 162 games isn’t all that difficult — or at least not compared to what it’s taken to make the playoffs in the past — But being specifically good over a less than two week stretch where you may have more off days than game days is quite a sticky wicket, and it flies right in the face of conventional baseball wisdom.
So with that, what type of team on paper would be best equipped to handle such a strange stretch of baseball? Here’s a list of items that comes to my mind from the pitching side:
- Elite starting pitching at the top of the rotation.
- Healthy starting pitching at the top of the rotation.
- Rested starting pitching at the top of the rotation.
- Elite relief pitching at the back of the bullpen.
- Healthy relief pitching at the back of the bullpen.
- Rested relief pitching at the back of the bullpen.
And here’s a much more complicated list from the positional side:
- Power in your lineup.
- Situationally aware players in your lineup.
- Clutch players in your lineup.
- Guys who can lock in / get in a groove quickly from regular to postseason game atmospheres in your lineup.
- Guys who can make adjustments with two strikes in your lineup.
- Healthy players in your lineup.
- Rested players (but not too rested) in your lineup.
- Speed and strong platoon options on your bench.
Doesn’t this largely sum up the Red Sox September dilemma? They don’t really have a healthy or rested roster right now, but it sure looks like they’re hell bent on getting one by the time September 29th rolls around, even if that means letting go of the rope a few times during a stretch that historically means pennant chase.
Garrett Whitlock to the IL to get some rest in late August? Sure. Tyron Guerrero the same right now? Why not? Push Sonny Gray back in the rotation? Yep! Align Payton Tolle’s starts so that he’ll have an extra off day all the way through the end of the season and be perfectly positioned to start Game 2 of a Wild Card series? Absolutely!
Did you purchase tickets to Tuesday’s game and get to see Jedixson Paez give up eight runs in 3.2 innings? That’s too bad, but the Red Sox weren’t making that one a priority.
On Wednesday, Dan Secatore wrote a great piece here on OTM about Adley Rutschman’s nagging elbow injury and how it’s important to beware of trade deadline hype. Well, I’m here to tell you that it’s still Okay to get hyped if you believe that suffering through Connor Wong for a bunch of games now means you might get a big playoff performance from Rutschman in a few weeks. I don’t care if Rutschman bats half his weight for the Sox in the regular season if helps him go 3-5 with a home run on September 29th. And I don’t care if he rests his elbow now if it better allows him to throw out the potential tying run in the ninth inning at second base on September 30th. Small sample size baby! That’s the game we’ve been reduced to.
Yesterday, our own Tim Crowley even took it one step further and went on to ponder if falling to the No. 6 seed would give the Red Sox an easier path through the playoffs. Again, all this is made possible because of the safety net of the completely unnecessary third Wild Card.
Oh, and as dirty as this feels, I can’t even blame the club for these actions. Just two weeks ago, I wrote about how Willson Contreras should’ve been put on the IL to rest up for when the games matter more. This is the reality when FanGraphs gives you a 97.1 percent chance to make the playoffs, but just a 0.3 percent chance to win the division.
Because do you know what else FanGraphs says about Boston’s chances? They have a 6.5 percent chance to win the World Series (over 20 times higher than their chances of winning the division). So you’re better off trying to fatten up those odds by prioritizing health and rest in September when the other two figures are virtual locks.
Again, it’s not really baseball, it doesn’t feel right on the night’s you’re doing it, and there’s no guarantee it’s even going to work, but if you think it’s going to bump your World Series odds, you get out your quill and sign the pact with the baseball devil.
Oh, and while we’re down this portal to hell, do you want to really get in the sheets with Satan? How about rooting for the Yankees? Currently, New York is just 3.0 games behind the Rays for the AL East lead with a SIGNIFICALLY easier schedule. Not only do the Rays still have to play Texas, Atlanta, Philadelphia, Houston and Boston, but they also have a four game set with the Yankees at Yankee Stadium near the end of the month in games 156 through 159.
If the Yankees draw close enough, Tampa and New York being better than the Red Sox over 162 games could actually work to Boston’s advantage if they each end up burning resources during the final few games of the season trying to win the division. The Red Sox meanwhile can spend that weekend exchanging love letters with the Cubs admiring how awesome each of their ballparks are and end up fully rested up for Tuesday, September 29th.
I don’t know if it will work, but I do know those first two legs of the MLB postseason are a complete mayhem machine, and figuring out how best to survive MLB’s crunch from twelve teams to four is the new holy grail of championship building. The sport has thoroughly and publicly figured out how good baseball teams are built in large sample size, but it hasn’t figured it out in small sample size yet.
Again, I don’t know exactly what that’s going to look like (nobody does), but I can take a guess; and it’s pretty clear the 2026 Red Sox are trying to align themselves to tackle that puzzle. It’s no longer about the marathon, it’s about positioning and peaking at a very specific moment. The Sox are trying to do this with a bunch of things we can see above the surface, and I’d bet my bottom dollar they’re also doing it with things we can’t see below the surface.
That’s the story of September. That’s the deal they’re making with the baseball devil. The sins may come with a very hefty price tag for throwing away some of these games down the stretch, but if the Red Sox do manage to punch their playoff ticket, navigate through the mess, and make it all the way to Game 7 of the World Series, it will all appropriately pay off on Halloween night. That’s just the sort of thing a baseball fanatic might sell their soul for.
