4 missed opportunities for Yankees at 2024 MLB trade deadline

If you're upset about the New York Yankees' trade deadline, we don't blame you. There's an argument to be made that not enough was done to fix an incomplete roster that nearly collapsed over the better part of the last two months.

If you're content with it then ... well ... you're lying. Just kidding. Everyone can have their preferred baseball opinion. Ours is somewhere in the middle. Brian Cashman did a good job of acquiring key pieces and minimizing risk, but he didn't drop the hammer at a deadline when it felt like he really needed to.

There were multiple ways to do it, too. He could've sent a few current Yankees packing and exercised some ruthlessness to send a message to the clubhouse. He could've "overpaid" for a superior talent that had the chance to put the lineup or pitching staff over the edge.

In the end, it was Jazz Chisholm Jr., Mark Leiter Jr. and Enyel De Los Santos heading to New York. That's one (1) impactful bat, one (1) impactful bullpen arm, and one (1) arm that will be designated for assignment before September. Doesn't feel that great, does it?

4 missed opportunities for Yankees at 2024 MLB trade deadline

Not Moving on From One of Gleyber Torres, Alex Verdugo, DJ LeMahieu

The Yankees are putting trust in their guys. We can't hate on it, but we can be skeptical ... even if all three have heated up lately. The larger body of work refutes that the streak will last, however, and Torres has especially proven to be a detriment to this roster in more ways than one. We don't have to go deeper into that. All you need to know is that he's still a below-average hitter and leads all MLB second basemen in errors.

As for Verdugo, he's a free agent after this season. There was a way for the Yankees to free up that money, welcome Jasson Dominguez back into the fold, and be more than content with Trent Grisham coming off the bench. Per rumors, there was interest in Verdugo, too. For two months, he was one of the worst qualified hitters in the sport. It appears he's breaking out of that slump, but that was enough evidence for us to say, "OK, we're good. Find somebody else."

Then there's DJ. The Yankees had no feasible way to get rid of his money because no sane team would take on that contract. And if he's the last guy on your bench because of that, then fine. But to still employ this trio after what we just witnessed over the first half (as well as the last few years for Torres and LeMahieu), it really felt like the Yankees didn't get much better, even with Chisholm in the fold.

Opting Not to Insure First Base or Third Base

Speaking of Chisholm, he's not a third baseman. But he's playing there because Torres expressed no interest moving off second base. We understand the thought process of acquiring as many good hitters as possible and figuring out the alignment later, but Torres and Chisholm are league-average hitters at best. This isn't like signing Bryce Harper and putting him at first base.

That means we're looking at a non-third baseman as the starter from this point forward, with DJ LeMahieu/Oswaldo Cabrera serving as the backup options. 'Waldo has been great in part-time duty, so we've got nothing bad to say about him. Chisholm has looked good defensively over there so far, but how can we really know?

On the other side of the diamond, Ben Rice is the first baseman with LeMahieu as the backup. Rice feels like he's improving by the day as he works out the kinks, but is he the starter when the playoffs arrive? Even worse, are the Yankees going to give the job back to Anthony Rizzo when he returns from injury? This is another very imperfect situation with nothing concrete about it.

Call us crybabies, but it feels irresponsible to have these kinds of question marks at first and third while you're also getting largely unsuitable production from second base and left field.

Failing to Capitalize on Nestor Cortes' Value (After Yusei Kikuchi Trade)

When the Blue Jays traded Yusei Kikuchi to the Houston Astros for a package of three top prospects, Cashman should've been going down the list of teams that needed a starter in his rolodex and making calls one by one.

Rumors surfaced that the Yankees were shopping Cortes, but nothing came to fruition. We wouldn't have supported trading Cortes and then not addressing the rotation/bullpen in response, but there were also opportunities to do that. It also wasn't a bad idea to keep Cortes, but if there was a way to creatively add more offense or re-stock the top of the farm system, it felt like a no-brainer to trade him and then go the distance for somebody like ...

Not Beating Dodgers' Trade Package for Jack Flaherty

Yeah! Why not?! With Cortes all but officially destined for the bullpen when Clarke Schmidt returns, the Yankees could've gotten a ton of value in a trade because he has one more year of team control. Then they could've felt comfortable outbidding the Dodgers for Jack Flaherty.

Well, either that, or they could have gone beyond Cashman's comfort level when it came to "matching up in value," which he cited as the reason a deal didn't get done with the Tigers. Were the Yankees actually concerned about Flaherty's back, or was Cashman being unreasonably stubborn about ensuring the deal was as fair as it could possibly be to his liking?

The Dodgers ended up trading their Nos. 8 and 22 prospects in Thayron Liranzo and (former Yankee!) Trey Sweeney. That really didn't seem steep for 2-3 months of Flaherty, even if he was dealing with some sort of a back issue in the medical review. And even going a bit beyond that to move the needle for Detroit felt like it wouldn't have the Yankees regretting much.

But that's the problem with the Yankees' trade deadline showings. They always lack creativity and they rarely feature the "go for the jugular" move. In previous years, it has failed miserably. We're hoping for a different outcome in 2024, but if not, all the warning signs were there.