New wrinkle from Yankees-Tigers Jack Flaherty trade talks makes NYY look way worse

The one area of the roster the New York Yankees didn't need to upgrade at this year's trade deadline was the starting rotation. They had one of the deepest and best groups in the league, even with all the time Gerrit Cole missed.

But as every fan knows, you can never have too much pitching. And the Yankees' bullpen wasn't exactly ironclad. The unit got the job done, but there were many holes, and it appeared to be more of a house of cards rather than a steel structure.

So when Brian Cashman's trade deadline featured the acquisitions of Mark Leiter Jr. and Enyel De Los Santos, most knew that wasn't enough. Even worse was the fact the Yankees reportedly had a deal in place for then-Detroit Tigers starting pitcher Jack Flaherty.

Flaherty helped the Dodgers defeat the Yankees in Game 1 of the World Series with a solid outing, even though he departed when LA was losing. He was a savior for the Dodgers, who lost Tyler Glasnow, Clayton Kershaw and Gavin Stone this season and had all of Shohei Ohtani, Tony Gonsolin and Dustin May unable to pitch since the start of the year.

In essence, the Dodgers had to make this deal, while the Yankees could have purchased the luxury at a reasonable price while keeping their NL counterpart from patching up a serious deficiency. Cashman reportedly ending up withdrawing from the deal due to concerns with Flaherty's medicals, which wasn't what got Yankees fans mad — it was the package the Dodgers sent in return that had everyone up in arms.

New wrinkle from Yankees-Tigers Jack Flaherty trade talks makes NYY look way worse

And, as it turns out, the Tigers were eyeing Yankees top pitching prospect Will Warren as the centerpiece of the deal, per Jon Heyman of the New York Post, while the Dodgers sent Trey Sweeney (a former Yankees top prospect!) and catcher Thayron Liranzo to Detroit.

The Yankees had high hopes for Warren, eh? Well, he was terrible in 2024. The right-hander had a 5.91 ERA and 1.40 WHIP in 23 starts for Triple-A Scranton as well as a 10.32 ERA and 1.90 WHIP in six games (five starts) in the big leagues. His strikeout numbers remain encouraging (165 Ks in 132 1/3 innings), but everything else turned out terrible.

Now, we don't know who else the Tigers were asking for because they definitely weren't settling for a single prospect, but did it really matter unless it was Jasson Dominguez, Spencer Jones or George Lombard Jr.? There aren't many more can't-miss prospects in the Yankees' system, so Cashman bypassing an opportunity to further fortify the MLB roster in a championship-or-bust season while stealing from a rival looms larger than one might think, even after all this dust settled. And especially as Flaherty prepares to lock horns with Gerrit Cole again in Game 5.

Instead, the Yankees continued to hobble down the stretch with all of Clarke Schmidt, Nestor Cortes and Luis Gil hitting the IL at some point. They continued to strain the bullpen as a result. They used Warren in various punt games (they were 2-4 when he pitched). They released De Los Santos and essentially exiled Leiter Jr. as the two completely fell apart.

Flaherty could've at least helped give the Yankees another consistent, above-average starter for the next three months, and it could've helped them get more creative with their bullpen when the playoff arrived (maybe Schmidt and/or Gil both became long relievers to help rest the high-leverage arms), who knows.

But they cheaped out again. Meanwhile, the Dodgers got better, avoided panic, and then took a powerful lead on the Yanks in the World Series. Can't say this inaction didn't influence the remainder of the year.