Yankees

Yuckey Way

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The Boston Red Sox have been eliminated from postseason play after a humiliating two-game sweep at the hands of the New York Yankees. The Yankees took Game 1 by a score of 9-0 and Game 2 by 9-2. That’s an 18-2 aggregate, the most lopsided Wild Card Series since the current format arrived in 2022.

The Red Sox never had any momentum, beginning the series with 14 straight scoreless innings across the two games.

This Red Sox season never really felt right, and even during their incredible 32-5 run that saw them vault from the depths of the AL East to snatching a Wild Card spot, I was always waiting for the regression back to the mean.

It turns out the summer sizzle was in fact a dead cat bounce, as the Sox limped their way through a 12-12 September before getting bounced by their arch nemesis.

Interestingly enough, they never actually played any October baseball this year, with yesterday’s elimination game occurring on the 30th of September.

Let’s take a look at my mid season analysis of the team heading into the trade deadline:

The impact of the expanded postseason on the trade deadline can’t be understated. It is one of several factors that has rewritten how the midsummer major league musical chairs play out. With two additional Wild Card spots, significantly more teams are in contention this time of year than would have been before. My old friends, the Boston Red Sox, who have had a disastrous year by all accounts and expectations, sit just 2.5 games back from the third Wild Card spot. They sit at 43-48 today, a better record than the vibes and the Boston media coverage would indicate.

While they have found some momentum lately, including a recent sweep of the Yankees, they have no business considering themselves buyers at this deadline. But the slim possibility of a returning Crochet and Anthony, along with Craig Breslow’s desperation to save his general manager job, could have them thinking twice at the deadline three weeks from now.

The Red Sox need to sell; starting with Sonny Gray, Aroldis Chapman, and Jarren Duran. Restocking the cupboard that has borne less fruit than expected with the triumvirate of Roman Anthony, Marcelo Mayer, and Kristian Campbell — from varying degrees of disappointment to disaster — should be the priority. The faltering young core has them much further away from a championship window than it appeared just four months ago.

Breslow is also proof positive of the harm playing fast and loose at the trade deadline can do to a team. He gave up James Tibbs for two months of the herbivore Dustin May, and then, this past offseason, sent Kyle Harrison — one of the top left-handed pitching prospects in baseball, owner of a 2.82 ERA that has swelled a bit after a few recent rough starts, and the headline piece coming back in the Devers deal — to Milwaukee for Caleb “What is baseball?” Durbin. I think Caleb knows what baseball is, but he doesn’t often play like it.

To be fair, when the Caleb Durbin trade was made, I didn’t hate it. In hindsight, giving up such a young and capable arm in Kyle Harrison was a mistake, but the intention in getting younger and cheaper at third with a competent piece like Durbin after losing Bregman to Chicago made sense.

Now, John Henry’s unwillingness to kick in an extra $10m over 5 years to Bregman cost them both the veteran right-handed hitter, as well as Harrison, who went 11-5 with a 4.20 ERA across 110-plus innings for the Brewers this season.

That’s a far greater cost than they realized they would be paying, and an argument for cheaping out when you’re the third-most valuable franchise in baseball not being a winning strategy.

They probably did just good enough for Breslow to keep his job, and for John Henry to keep trying to poor-boy this team back into contention.

Talk about losing the battle, but (also) losing the war.

Photo: Bernard Gagnon / Wikimedia Commons — CC BY-SA 3.0

Evil Equity Empire

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George Steinbrenner famously said he wouldn’t sell the Yankees for anything, that “owning the Yankees is like owning the Mona Lisa. You don’t sell it.” It appears Apollo Sports Capital have finally cracked the da Vinci code.

The $2.6 billion from Apollo Sports Capital buys an undisclosed minority stake in Yankee Global Enterprises and refinances the franchise’s existing debt. Apollo Sports Capital CEO Al Tylis takes a newly created seat on the YGE board. Hal Steinbrenner and the Steinbrenner family retain full control, with Steinbrenner saying the partnership “allows us to explore pursuing strategic opportunities.”

—Sportico

Is this the Yankees finally capitulating to the Dodgers’ dominance and deciding the equitization route is the only way to level the playing field?

For all my grievances with the Yankees, I have respected that they have not been as willing to bend to modernity as the rest of the league. Abstaining from a City Connect uniform, and until recently holding to a rigid facial hair policy. But it looks like the times may have finally caught up with the Bronx Bombers.

What does this foreshadow about the likelihood of a salary cap being instituted, one the MLBPA has already said they will never accept?

Would the Yankees have still made this move if they truly thought a hard salary cap was a inevitable? A change expected to raise franchise valuations even higher.

Debt restructuring is one of the key reasons listed by New York for the move. Though the remaining debt on Yankee Stadium is reportedly under $100 million, which makes $2.6 billion an awfully large hammer for that particular nail. It could also signal Hal Steinbrenner is anticipating the top of the market is approaching, and is cashing out serious profits on what he views as an acceptable valuation of his franchise.

Most importantly, it could be the Yankees getting much needed liquidity to survive a long work stoppage that looms after the CBA ends on December 1st. If that is in fact their primary motivation, it’s another sign we could be in for a long and bloody battle between the owners and players over the next 18 months.

This sort of deal rescued FC Barcelona from falling behind, and it looks like the Yankees have it in mind to follow that blueprint. But whereas Barca sold a 25% stake in future media rights, the Yankees have sold a minority stake in Yankee Global Enterprises — not just the ballclub, but the holding company that also owns 26% of the YES Network, roughly 16% of Legends Hospitality, and 10% apiece of AC Milan and New York City FC. MLB rules cap a single private capital fund at 15% of a franchise, so there is a ceiling on how much of the Bronx is actually for sale.

On the other side of the rivalry, Red Sox ownership Fenway Sports Group is closing in on selling a minority stake in Liverpool FC to a consortium that includes Jeff Bezos. Fenway Sports Group have made enormous gains on their Liverpool acquisition — they bought the club for £300 million in October of 2010, and the reported deal values it at roughly £4.4 billion today, with the consortium’s one-third stake going for somewhere around £1.4 billion. I’d love to imagine John Henry is willing to sell the Red Sox, preferably in their entirety, as well.

The Yankees now have the capital to keep pace financially with the Mets and Dodgers, at least for a while. Those two franchises may also exhibit their new ceiling, and in the LOL Mets case, their new floor.

Photo: Matt Bolton / Wikimedia Commons — CC BY-SA 2.0

Trade Winds

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The 2026 Major League Baseball trade deadline has come to pass. There was a flurry of activity Monday afternoon that provided some surprising moves, none of which were exceedingly shocking.

The big news of the trade deadline actually broke late Saturday evening when it was announced that the Los Angeles Dodgers have come to terms on a trade with the Detroit Tigers to acquire ace lefty Tarik Skubal.

Skubal is the back-to-back reigning American League Cy Young winner, and the first reigning winner to be traded in-season since Justin Verlander in 2023 — only the sixth ever. He led all of baseball in WAR and strikeouts in 2024 and went a combined 31-10 with 469 punchouts across 2024 and 2025. There was talk he may not be traded at all this year after he had loose bodies removed from his elbow in May and was back on a mound 38 days later. The Dodgers are now the first team in league history to have a reigning two-time MVP and a reigning two-time Cy Young winner on the roster together in the same season.

Unlike most baseball fans, I was happy to hear the news. The most important reason for that is my hope was that he would not end up on the New York Yankees. The Yankees had a rather quiet deadline, but they did acquire Luis Garcia Jr. from the Nats, he leads the NL in slugging percentage. GM Brian Cashman seems to like his team’s chances should they get Judge, Stanton and Bellinger back healthy before the end of the season. 

Failing to acquire Skubal hasn’t cost the Yankees much in the way of championship odds with only a slight drop from +550 Sunday afternoon to +600 Tuesday afternoon.

I screencapped two sets of odds to track the movement on FanDuel, giving a wide enough birth from the deadline itself to still get a reasonable picture of the changes it brought: 

Sunday at 5 PM: 


Tuesday at Noon: 


The question that I have for the Yanks is— what would their odds currently be had they acquired Skubal?

What would the third most favored team, the Milwaukee Brewers (+950 odds) odds be if they’d acquired Skubal?

A key reason to ask, is that the Dodgers didn’t give up a whole helluva lot to get the superstar pitcher — outfielder Zyhir Hope, the No. 5 prospect in their system and No. 25 in all of baseball, right-hander River Ryan at No. 7 in the system and No. 68 overall, and right-hander Brady Smith at No. 17, per MLB Pipeline. Los Angeles managed to hold onto their top four prospects and still get a nuclear arm added to their arsenal. 

The Dodgers sit at an unprecedented +155 to win the World Series in early August. That speaks to the incredible team they have constructed, and also the weaknesses of the rest of the field.

A three-peat would give them the first one since 1998-2000, when the Yankees pulled it off, it would also elevate the cries of the Salary Cap hungry owners and the majority of MLB fans who support such a measure.

Seeing a cap and floor model in the vein of the NFL would give fans a sense that any team could win it all. Just don’t tell that to Cleveland Browns fans, hell, don’t even mention it to Bills fans. Teams that scout, draft, recruit, sign, develop and take care of their players will still have an enormous advantage, and those in low-tax, high-revenue, nice-to-live locations will have built in advantages that will become more stark in a hard capped league. 

Point being, don’t expect a salary cap to fix all your franchises woes overnight, but I do understand the appeal and would love to see what America’s pastime looked like with a more level playing field.

Other noteworthy items from the deadline:

The Boston Red Sox basically dumped one of the members of their golden age of prospects they’ve been championing for the last several years. The oft-injured Marcelo Mayer never found his groove in the big leagues, and made more headlines for his attitude and alleged off-the-diamond issues. Word is the organization felt he was detrimental to the prospect they just locked up for nine-figures last summer in Roman Anthony. Mayer was said to be a regular fixture of the New England late night scene (according to 98.5 The Sports Hub of Boston), which fed into questions about his motivations and maturity. He was shipped to the San Francisco Giants for lefty reliever Erik Miller and minor-league outfielder Carlos Gutierrez.

The Red Sox also paid a pretty heavy price to nab Adley Rutschman from the Baltimore Orioles. The switch hitting catcher is currently injured, but could provide a valuable dynamic to the Red Sox lineup heading into the final stretch of the season, and the postseason should they land a spot. I quipped that the Red Sox are now going after players who are “pre-injured”, as another key acquisition before the deadline was Curtis Mead, the former Nationals second-baseman who has some serious pop in his bat right now and could provide much needed defensive stability to the Red Sox middle infield, was injured in his first game with the Sox. A pitch struck and broke his wrist. He now heads to the infirmary with ace Garrett Crochet, who hasn’t pitched since April 25 and still hasn’t picked up a baseball after shoulder inflammation turned into a lat strain, Roman Anthony, out since May 5 with a torn ligament in his hand and no timetable, shortstop Trevor Story, on the 60-day list since sports hernia surgery in late May and only now aiming at a rehab assignment. Rutschman officially begins his Boston tenure on the 10-day list with left wrist inflammation. Which when you compare it to the medical report I just got done delivering, is actually pretty healthy! 

Boston moved from +3500 odds on July 13, to +1800 on Sunday afternoon, climbing as high as +1500 after the acquisition of Rutschman before settling to their current line at +1600. Still a dark horse by those odds, but third behind division rivals Tampa and New York in American League team odds to win it all.

The Atlanta Braves were quiet at the deadline, their odds have dropped slightly as a result. But Chris Sale did win July’s NL Pitcher of the month, and the Bravos still have big October aspirations.

My recent article, The Dead Tradeline, discussed how the expanded Wild Card slots (and the longstanding inability to trade future draft picks) makes for less excitement at the trade deadline. Far more teams being “buyers” now than sellers limits the amount of top end players who are available to be moved, and not trading future picks limits the amount of resources teams have to acquire them. I discussed how the Red Sox could greatly benefit by being deadline sellers, but their improbable win streak, and Breslow’s desire to save his General Manager job, had made that highly unlikely. The Red Hot Sox haven’t slowed down yet, having just completed a sweep of the Dodgers this past weekend, placing them at a mind-blowing 28-5 since June 24. 

The last few weeks have felt like a holding pattern as we waited for the deadline to come and lock in the rosters. Now that we’ve seen its fruits come to bear, the headline that remains: the rich get richer in LA, the Yankees don’t make major waves, and the odds of a serious labor stoppage that puts the 2027 season at risk have grown ever higher as the owners will seek to use the Dodger’s success as the smoking gun that demands a salary cap at all costs. 

So enjoy this postseason run, it may be the last one we get for a while.