Will the Yankees Make the Postseason?

Mid-August, thoughts by Cary Greene

August 12, 2025

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NOTE - This was written on Sunday before being published today.

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With the Yankees continuing to drop like a rock in the standings, I’m beginning to wonder if the Yankees will manage to slide out of the postseason picture entirely. Certain contending teams that are direct threats to the Yankees' playoffs hopes have come into focus in the

aftermath of what was a fascinating Trade Deadline.

Since the Deadline, both the Red Sox and the Mariners have blown past the currently imploding Yankees in the Wild Card Race and now, at the time of this writing, the Guardians and the Rangers sit right behind Hal Steinbrenner’s Yankees.

Less than 46 regular season games remain on the Yankees schedule, which is the 26th easiest remaining schedule in MLB per Tankathon.com. Possessing the 20th easiest remaining schedule, which equates to a downhill jog through the park, the Guardians have a very realistic shot at nosing the Yankees out of the playoffs entirely. There is no doubt the Guardians are playing great baseball of late, they’re 20-10 in their last 30 games and they’re 8-2 in their last 10 games.

The Red-Hot Guardians:

It was a surprisingly quiet Deadline for the Guardians this year. In a salary dump maneuver, Cleveland GM Michael Chernoff traded former Cy Young Award winner Shane Bieber to the Blue Jays in exchange for Double-A righty Khal Stephen, whom BaseballTradeValues.com projects to be worth $9.8 MTV.

While Stephen is absolutely a promising prospect, he likely won’t be impactful to the Guardians this season whereas Bieber might have been a huge difference maker not only for the stretch run, but in the playoffs as well. In the aftermath of the Bieber trade, I was left wondering, could the Yankees have landed Bieber for, say, Bryce Cunningham, whom BTV projects to be worth $10.9 MTV? Possibly, but it’s obvious that certain teams simply don’t give the Yankees any discounts and the Guardians have absolutely been one of them over the last Decade or so. We’d have to go back to the Andrew Miller to the Indians trade in 2016 to find an example of the two teams matching up on a big trade. Also, perhaps Cashman attempted to do that and who knows, maybe the Guardians just liked Stephen better.

Cleveland also traded reliever Paul Sewald to the Tigers, in what appeared to be a salary dump of roughly $2-million. Add that to the $19 million they saved by trading Bieber away and what is readily apparent is the Guardians have serious budgetary forces at play within the organization. Even though they’ve turned into a legitimate contender, the Guardians organization is not fond of spending big in order to win. Cleveland has the 25th lowest payroll in MLB this season, coming in at just over $97.6 million.

Perhaps the biggest move the Guardians made at the deadline was actually the one they didn’t make, as they hung onto Steven Kwan despite receiving heavy trade interest. Beyond that, the Guardians did nothing more than claiming right reliever Carlos Hernandez off of waivers from the Tigers. Given that Guardians only got worse at the Deadline, and also factoring in their slightly harder schedule - the question is: Can the Yankees stave the Guardians off down the stretch and manage to secure a postseason berth?

With Cleveland playing as well as they are of late and seeing as how the Yankees have been terrible in contrast, it seems extremely doubtful that the Yankees can hold the Guardians off from advancing past them in the Wild Card standings.

The Rangers Have an Uphill Ride:

Another contender, this one with the second most difficult remaining schedule of all contenders, is the Rangers - who are another direct threat to bouncing the Yankees from the playoffs. They too refused to sell at the Deadline. Texas now sits a mere 2 ½  games out of the Wild Card at the time of this writing and it feels like they’re riding hard, yet, they do face the League’s 4th most difficult remaining schedule. Texas is 4-6 in their last 10 games but they’re 17-13 in their last 30 so they’ve been inching closer and closer in the Wild Card standings. Should the Yankees keep playing the way they have been, Texas could easily catch them.

Choosing to add to their already very good pitching staff, the Rangers bolstered their rotation at this year’s Deadline by adding Merrill Kelly from the Diamondbacks and he’ll slot in behind the dominating duo of Jacob deGrom and Nathan Eovaldi as the team makes their postseason push.

Also added were lock down middle reliever Phil Maton and lefty Danny Coulombe. All things considered, the Rangers now have one of the MLB’s top pitching staffs. Personally, I was hoping the Yankees would trade with the Cardinals for Phil Maton, as I had him ranked as a Deadline priority for Cashman. The Cardinals must have really wanted two emerging pitching prospects, a lefty and a righty, with big strikeout numbers and solid control and that’s exactly what they received back in the form of Sklyar Hales and Mason Molina.

Despite frequent talks between the Yankees and the Cardinals, Cashman and the Yankees didn’t make a push to acquire him. Personally I thought as the Deadline approached, he was far preferable of a trade target than, say, Jake Bird - who has already been optioned to Triple-A after being horrendous as a bridge reliever for the Yankees.

Maton, who owns a 192 ERA+ this season and who hasn’t allowed a run since the Rangers acquired him, would have looked great in pinstripes but I can’t pretend to understand Brian Cashman and his decision making team. Going back to this past offseason, I thought Maton would have been an ideal free agent acquisition, yet Cashman decided to give up both Nestor Cortes and Caleb Durbin in acquiring Devin Williams. It was Cashman’s poor structuring of the Yankees bullpen then, that put the Yankees in the position of having to make numerous trades to fix it at this year’s Deadline.

Though the Rangers do have a proportionately more difficult remaining schedule than all of the other contenders, save for the Reds, the moves the Rangers made make them a formidable Wild Card contender and a direct threat to the fading Yankees playoffs lives.

With the Game’s number four rated pitching staff, a rotation and bullpen that owns a 113 ERA+ this season, make no mistake, the Rangers have what it takes to pull into the postseason this year and their front office clearly knows it. The Rangers, who needed rotation depth, bullpen help and a run producing bat decided to double down on pitching and keep most of their best prospects like the Yankees did. Will their strategy pay off?

Division Rivals the Yankees are Now Chasing:

Toronto used this year’s Deadline to fix their key areas of need - namely the bullpen, bench depth, first base and they even made what some insiders are saying was the single best Deadline trade, acquiring a lottery ticket for their rotation - in the name of Shane Bieber - who has looked spectacular in his rehab starts by the way.

Besides the coup of landing Bieber, the Blue Jays also notably netted another reliever that many wanted Cashman to acquire from the Twins - lights out righty Louis Varland. He has pitched to a lights-out 211 ERA+ this season. Despite Cashman’s constant nosing around the Twins organization, to the point of them finding it annoying, no deals materialized and Cashman let the Twins very good relievers like Varland and Johan Duran wind up in other contending teams' bullpens.

There’s no doubt Toronto’s bullpen will benefit from the presence of Varland and if Bieber does come back like his former self, he could make the Blue Jays dangerous in the playoffs. With the sixth most difficult remaining schedule in MLB, the Jays will need to continue to over achieve in order to win the American League, as the Red Sox have their sights set squarely on winning the East this season and their gaining ground rapidly of late.

MLB’s scheduling hasn’t been kind to the Blue Jays aspirations of winning their Division, they still have to play series against teams like the Brewers, Dodgers, Cubs, Astros, Red Sox and Yankees and this will set the stage for what will likely be a tightly contested stretch run in the American League East.

Up in Beantown, the Red Sox have blown past the Yankees in the Wild Card Standings and now sit a mere three games behind the Blue Jays. Boston is 22-8 in their last 30 games and they came out of the break red hot as well as they’re 8-2 in their last 10 games.

Lurking mostly on the back pages of the sports section at this year’s Deadline, Boston’s chief baseball officer Craig Breslow only managed to bring in lefty reliever Steven Matz in a trade with the Cardinals and righty Dustin May in a deal with the Dodgers. Though the Sox were connected to Joe Ryan of the Twins, the Marlins Sandy Alcantara, the Diamondbacks Zac Gallen and Yandy Diaz of the Rays, Breslow was unsuccessful at acquiring any of the controllable starters he targeted.

Possessing the seventh best rated overall team pitching in MLB this season, the Red Sox one glaring weakness is that they lack a second stopper to slot in behind fireballer Garrett Crochet. While Brayan Bello has made a solid improvement this season, the rotation falls off a bit after him and Lucas Giolito. Can the Red Sox bullpen continue to make up for the team’s lack of depth in their starting rotation? Currently the Sox are showing no signs of slowing down and their remaining strength of schedule is ranked a manageable 16th in MLB.

There is a very strong probability that the Red Sox, if they can continue their torrid current pace, will be able to overtake the Blue Jays down the stretch.

Currently clinging to the final Wild Card spot, the Yankees have one remaining series against the Blue Jays and two against the Red Sox. Also, the Yankees don’t play head to head against the Rangers, Guardians or the Mariners from here on out. In order to make the playoffs, the Yankees need to take care of business against a very weak remaining schedule. This gives the Yankees a big advantage with only 45 games remaining.

Tankathon.com tabulates that the Yankees remaining opponents have a combined .482 winning percentage.

Can the Yankees Make the Playoffs?

Thus far, the easy remaining schedule isn’t helping the Yankees much though as New York is only playing .467 baseball in their last 30 games. It’s hard to imagine that MLB’s 26th easiest remaining schedule, which the Yankees face, is composed of teams who are currently playing better than the Yankees are! Yet, them’s the facts. Aaron Boone has the Yankees playing in full bottoming out mode these days.

FanGraphs rates the Yankees chances of making the playoffs at 82.3 percent and they give the Red Sox a worse 76.6 percent chance so they must know something I don’t know. It sure seems like, these days, the Yankees have a worse chance than the Red Sox do of making the playoffs. Coincidentally, FanGraphs rates the Mariners chances of making the playoffs at 91.5 percent, they say the Guardians chances are at only 31.7 percent and the Rangers are only at 25.0%.

Clearly FanGraphs doesn’t emphasize whether or not a team is currently playing well or playing poorly. Personally I do think this has to factor in. How else can a team like the Brewers be explained? Nobody thought they’d be putting it all together like they have, but here we are. The Brew Crew has been easily the best team in Baseball, at 24-6, over the last 30 games and they aren’t showing any signs of slowing down either. Milwaukee has been playing the 5th most difficult remaining schedule and it hasn’t mattered in the least.

Just think, as good as the Brewers have been recently, the Red Sox are right there with them, Boston is only 2 games worse. Yet, FanGraphs says the Brewers have a near certain 99.8% chance of making the playoffs and the Red Sox chances meanwhile are worse than the Yankees? I’m not buying it. That FanGraphs rates the Guardians chances at only 31.7 percent is also sincerely questionable. They’re playing great these days, but granted, they do face a tough remaining schedule. Still, I’d give the Guardians at least a 75% chance of making the postseason.

Given that there are only 46 games left, I’d rate the Yankees chances of making the playoffs at less than 50% right now and I’d likewise give the Red Sox a much more favorable 90% chance. In fact, I’ll say it right now. I think the Red Sox will win the American League East. For whatever reasons, they’ve come together as a team and they’re doing a whole lot of winning these days.

My Unfortunate Assessment:

Making the playoffs would require the Yankees to do a complete and utter about face. A lot would need to change and it would need to happen fast. I just don’t see Aaron Boone making this happen. Currently, the Yankees possess a team ERA+ of 102. This means that they have barely above average team pitching. I’m sorry folks, that’s not going to be good enough to carry the Yankees into the playoffs - now when the Guardians boast a 110 ERA+ and the Rangers are at a 113 ERA+. Heck, the Red Sox are at a 112 ERA+ too for that matter. All of these teams, the Guardians, the Rangers and the Red Sox have vastly superior overall pitching than the Yankees do.

All of these teams are also playing a whole lot better than the Yankees currently are. These are the facts and I don’t give a hoot what FanGraphs says. We shall see if FanGraphs is smarter than I am, but this year I really don’t believe they are.

Cashman built the Yankees around Aaron Judge and as Judge goes, so go the Yankees. Judge has posted a .650 OPS since he came back. He’s playing hurt and it shows. In order to completely turn the Yankees around, it would have to start with Judge catching fire, but even then, the Yankees just don’t have the necessary pitching to hold off the contenders they’re up against right now.

I’m not sure Giancarlo Stanton is capable of carrying the Yankees on his back, but he’d need to become an iteration of his former 2017 National League MVP self if the Yankees were going to suddenly start slugging their way to the postseason. I don’t see Judge heating up and Stanton hasn’t exactly been sipping from the fountain of youth these days. This Yankees team direly needs both Judge and Stanton to simply take over. If they don’t, the Yankees can kiss the playoffs goodbye. This team just doesn’t have what it takes.

Max Fried has a 5.80 ERA since July first. Over the same stretch, Carlos Rodon’s ERA is 4.50. There are zero signs that either of them are going to suddenly turn into Sandy Koufax, but that’s pretty much what would need to happen for the Yankees to suddenly do an about face.

This Yankees team is a team built around key stars like Judge, Stanton, Fried, Rodon and Cole. Without their stars playing like stars, the Yankees are a curious cast of characters who collectively, simply aren’t a postseason team. We’re seeing this play out right before our eyes. The Yankees came out of the break 4-6. They’re playing exactly the way they were heading into the break – they’re a sub .500 team these days and they’re doing nothing – nada – to show us otherwise.

I’ll conclude by saying, if you haven’t guessed this already, that the Yankees are going to miss the postseason this year. I’d kind of love to be wrong on this, but not really as I don’t want to see the Yankees offense get strangled by superior postseason pitching. I don’t want to watch the Yankees get bounced right out of the playoffs. In my opinion, the Yankees don’t deserve to make the postseason this year either. It seems like the whole baseball universe has known that Aaron Boone wasn’t the right manager for the Yankees. Yet no changes have been made, not even in a bold attempt to shake things up a little and see what happens.

Hal Steinbrenner is getting what he paid for. He runs the most overpaid, mediocre team in MLB. I hope he’s happy with it. He shouldn’t be, but I hope he is. He’s the one who continues to employ Brian Cashman and Aaron Boone. The Yankees are his team.

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Cover image from Microsoft Copilot.