Somehow, Brian Cashman's 2024 Yankees trade deadline might be his worst work yet

Have you noticed, by now, that it's not so easy to beat the system? That, 20 years after Moneyball, every MLB team is chasing the same "undiscovered" assets, so you might as well circle back to competing in a bidding war for the obvious targets rather than overturning a hidden stone everyone else has already discarded?

If you've noticed this trend, then congratulations. You're several steps ahead of New York Yankees general manager Brian Cashman, who believes this column is unfair. It's unfair to assess things that have happened. Repeatedly.

This particular summer, the Yankees, once flying high, needed a transformative deadline with higher-than-high upside to return to the spotlight. By simply patching holes, they'd place themselves in the mix for a title; after all, the field was wide open, with streaking teams like the Phillies and Orioles joining them in similar midsummer collapses. But by adding tried-and-true names and stomaching a few slight overpays, the Yankees could've separated themselves from the field, rather than being satisfied to tread alongside the others spiraling out of control.

New York struck first by adding Jazz Chisholm Jr., a consensus "overrated" star who would either thrive in the spotlight or continue attracting the wrong kind of attention. His first 14 games, at a position he's never played professionally before, indicated that the Yankees actually might've nailed this addition (seven home runs, positive defensive metrics). Unfortunately, a UCL injury felled him shortly thereafter. Even if he'd stayed fully healthy, his addition would've made far more sense if it had been paired with an exodus of losing players (Gleyber Torres?), allowing him to man his typical position, followed by further maneuvers to replenish depth (Amed Rosario?).

The illness afflicting this year's trade deadline doesn't have much to do with Chisholm, though. It was a solid pickup at a mid-tier cost, and represented the start of something good. Unfortunately, Cashman's malfeasance at addressing the Yankees' primary area of need seems likely to represent a permanent scar on a season that could've really gone places if it had been gifted the right talent transplant.

With Tanner Scott available -- at a high cost, but still -- the Yankees tried to add swing-and-miss to their bullpen with the addition of Mark Leiter Jr., blessed with a high-performing splitter, solid peripherals, and a 4.00+ ERA. With the Yankees, that ERA has risen to 4.63, as he sits 92 in the zone more often than not. They also fired off a last-second deal for Enyel De Los Santos of the Padres, a hard-throwing wild card who was susceptible to the home run ball in San Diego, to say the least.

He's already on the White Sox after allowing seven earned runs in an outing to the team that's on pace to be the worst in baseball history. That would be ... also the White Sox.

Yankees' bullpen decisions made 2024 trade deadline Brian Cashman's worst ever

In essence, Cashman's deadline hinged -- as it always does -- on banking on healthy and effective returns from Ian Hamilton, Nick Burdi, Scott Effross and Lou Trivino. On Aug. 19, the Yankees have yet to see a single one of those players ascend back to the bigs. Their closer is worn out, sloppy, or both. They needed a bullpen renaissance, spurred by no-holds-barred additions across the board. They received crossed fingers, someone who's already been cut, and yet another hurler whose metrics don't match up with reality.

If Brian Cashman believes he's smelled out a target that nobody else was smart enough to conceive of, odds are that smell is something else entirely. The Yankees needed a transformative bullpen deadline, and they didn't add a single reliable piece to the unit that every fan, casual or hair-torn-out, knows damn well could be the difference between a World Series run fueled by the Generational Juan Soto and Aaron Judge and also ran status in a winnable October.

The team that paid the high cost for Tanner Scott, by the way? 13-4 since the deadline. Some teams like it when you show faith in them.