Yankees vs. Red Sox preview and prediction for 2025 MLB Playoffs series

Look, there are going to be a lot of previews, breakdowns, guides, best-bets, predictions, and astrological-palm-readings before Red Sox-Yankees gets going on Tuesday at 6:08 p.m. ET. And you’re free to read them all, complete with their breakdowns of BABIP, barrel rates, attack-angle-heights, etc. If you want it, you can get it, and I love that for you.

But if you just want to understand the series from a totally casual perspective, and want the reasonably unbiased opinion of someone who has followed the AL East with fanatical intensity for months and has watched every Red Sox-Yankees game for like … most of my life, I’m you’re guy. You’re not going to come out of here an expert on the fine sabermetrics of this series, but you are going to know what’s going on and what to look for — not just from today, but from the history and importance of this glorious rivalry. It’s going to be a good time, and that is the Casual Guide Guarantee (CGG, patent pending). Let’s roll.

The Red Sox-Yankees Concept

The first good thing I ever published was a 500-word soliloquy for my college paper titled “I hate the New York Yankees.” But before you click off and declare that this preview is being written by a Red Sox fan with less-than-sound impartiality (it is), hear me out.

The crux of that piece was that I hate the Yankees regardless of actual context. It was a sports hate, existing only in the context of an ultimately-meaningless game we all care about, but it is real. And it exists completely independent of whether the Yankees had recently wronged me. I truly hope they feel the same way. 

That is the heart of what makes this series awesome: this isn’t two teams that hate each other, or two fan bases that hate each other, or even two cities that hate each other. These are two ideas that hate each other, having transcended the field of actual reality and morphed into a half-spiritual desire to beat each other in baseball games. 

For pretty much the whole history of the world, this was a one-sided rivalry: the Yankees would beat the Red Sox every year, all the time, and won a billion World Serieses on the way. But the last 20 years have been completely dominated by the Red Sox — the Yankees haven’t defeated Boston in the playoffs since 2003. I was seven months old.

But these are current teams, not a collection of historical factoids. And the Yankees have been far better in the last few years, losing in the World Series last year while the Red Sox haven’t made the playoffs since 2021. Despite some chaos in management and some less-than-stellar lineups, the Yankees have built an infrastructure that basically works. The Red Sox have built an infrastructure that… uh, might work. Let’s break down why these 2025 teams are so different. 

Why the Yankees could win this series

The Yankees have not been a steady ship this season at all, but it’s easy enough to understand who they are: the Bronx Bombers, who came within one Anthony Volpe home run of having their entire lineup hit 20+ home runs. They have hit by far the most home runs in baseball this year, lead in RBIs and walks, but also are third in strikeouts. In short, they swing the bat, and it’s either going in the catcher’s mitt or the parking lot. That could win you a three-game Wild Card series in a runaway, or it could lose you it in 54 batters. 

Look: they have the best hitter I’ve ever seen, and probably the best slugger ever if you ask the Baseball Hall of Fame (you shouldn’t ask them). Aaron Judge is so good, I can’t even hate him as a Red Sox fan — I was at a game where he struck out three times, then, on his fourth trip, got in a two-strike hole… before hitting a ball so far over the Green Monster it presumably landed in Weymouth. For the few seconds that ball flew, not one fan in Fenway Park was mad, just confused. None of us had ever seen a ball hit that hard.

Their pitching has not been nearly as legendary or even coherent, with Max Fried going from Cy Young contender, to worst-pitcher-on-the-team, to now being pretty damn good again. Along with Carlos Rodon, that’s a tough nut to crack for any team in a three-game series. But while their bullpen is full of name brands, it hasn’t been consistent at all this season. Ultimately, the Yankees will go as far as their home runs will take them, and their lineup can hit no matter what else happens to go wrong for them. Which is a much better thesis than I can write for the Red Sox…

Why the Red Sox could win this series

Boston has been a hilarious team this season, not always in the good, spunky ways. They have gone through stretches of complete unbeatability to straight up inventing ways to lose baseball games. Getting a hit with the bases loaded? We would never. No-name reliever make it through an inning with an 8-run cushion without forcing their god-tier closer into the game for no reason? No chance. 

When Roman Anthony was healthy, the Red Sox had exactly four whole things they could count on, but now they’re down to three (and they’re all pitchers… and two of them are named Garrett): Garrett Crochet, Garrett Whitlock, and Aroldis Chapman. Those guys are probably the only reason you can plausibly pick the Red Sox to win this series when their offense is suspicious at best and putrid at worst.

Crochet, however, was at worst the second-best pitcher in the American League this year, and has etched himself in Red Sox memory as a full-trust ace. When he’s on the mound, Red Sox fans simply expect to win. He can’t pitch every day, but he is the best weapon they have. Whitlock has complemented him perfectly, being a lights-out setup man to Chapman’s flame-throwing closer duties. If the MLB were like the NFL and everyone only played once a week, this is an unimpeachable pitching trio. They would basically never lose.

But their offense probably sucks, but even when it doesn’t, it makes no sense. At its peak, the Red Sox had Alex Bregman and Roman Anthony as everyday rakers that everyone could build around. Now that Anthony is probably out for the season and Bregman is cooled off, the Red Sox are relying on anything they can find somewhere in the dugout. Ceddanne Rafaela walk-off No. 6? Sure? Jarren Duran hustle-doubles? Bring it. Masataka Yoshida suddenly becoming Boston’s hottest hitter in the last month and becoming vital to the Red Sox lineup after being absolutely terrible for the rest of the year? You know it. 

If the Red Sox win this series, it will be because their starting pitching looked like it did at its peak this summer. Crochet is nails, but they need quality starts out of Bryan Bello and/or Lucas Giolito too. The bullpen is not built to keep the Yankees bats quiet for five entire innings. And should those bats get loud, I have very, very, very little confidence that the Red Sox bats have even concepts of a plan to keep up.

Yankees vs. Red Sox prediction for 2025 MLB Playoffs

It is my fiduciary responsibility to choke down my pride and say: Probably the Yankees. They’re at home, have significantly hotter bats and their frontline pitching is seeing the plate well. But that’s booooooooooooring. 

This is the AL Wild Card, one of the stupidest and most-chaotic constructions in modern sports. That above prediction is based on 162 games of data and evidence that suggests that the Yankees are likely to score more runs than the Red Sox in any single game. But we’re not playing 162 games, silly, we’re playing between two and three. 

What reigns supreme when you distill hundreds of thousands of individual data points down to at most 81 outs each? Chaos. Chaos is a ladder, say morally-dubious Game of Thrones characters, and the Red Sox are fit to climb it with their mix of elite pitching and psycho lineups that sub out like five whole dudes depending on if it’s a righty or lefty starter. This is insane! I love it!

Let’s be honest: both these teams could win, and a series this short is a complete crapshoot. I’ve merely laid out what these teams have been all season, but believe whatever you want to believe will happen — it’s probably just as likely as any other outcome. I choose to believe the Red Sox will win, because I can’t live with myself any other way. After all, I absolutely hate the Yankees.