Brian Cashman's responses to trade deadline reveal Yankees' exact problem

It's hard to be upset right now, and honestly it's better not to be. The New York Yankees are on a five-game winning streak and Jazz Chisholm appears to be closer to the "missing piece" for this lineup than anybody could've imagined.

Then again, it'd be irresponsible to say the Yankees "did enough" at this year's MLB trade deadline. They came away with Chisholm, Mark Leiter Jr. and Enyel De Los Santos. That is not a haul by any means, particularly when you're trying to win a World Series with many roster holes, and are only guaranteed Juan Soto through October.

So what happened? We saw Jack Flaherty go to the LA Dodgers for a very doable trade package. The relief market was fairly ridiculous, but Cashman smartly pivoted to Leiter Jr. There wasn't another reliever? The Rangers acquired Andrew Chafin from the Tigers in another reasonable deal. A's reliever Lucas Erceg went to the Royals for an elevated price, but nothing you spit out your coffee over.

And what about the position player market? The cost for Jazz was minimal, as we saw. Randy Arozarena went to the Mariners for barely anything. The Nats got three prospects for Lane Thomas, but some would argue that would've been worth it for a platoon option for Alex Verdugo, at the very least. The Dodgers got creative and acquired Tommy Edman and Michael Kopech in a three-team trade.

Once again, the Yankees opted not to get creative. They didn't out-bid other contenders for top talent. In frustrating fashion, this deadline was approached with the utmost logic.

Brian Cashman's responses to trade deadline reveal Yankees' exact problem

Cashman was called out by WFAN for the perceived "lack of urgency" with this team on many fronts. He refuted that immediately by asking Brandon Tierney to take a drug test and then followed it with platitudes about how they've previously signed/traded for big-name players. Sorry, but re-signing Aaron Judge two years ago, paying Gerrit Cole in 2019, and extending DJ LeMahieu in 2020 don't count. Those were moves that needed to happen for the Yankees to remain relevant. One of them also happened to turn into a major mistake overnight.

We'll give him the Soto trade, but again, that was a necessity because of how terrible the previous outfield acquisitions were/how badly the front office neglected center and left field. Soto represented an opportunity that couldn't be passed upon if this terrible 2023 roster wanted a seat at the table in 2024.

Props to paying Carlos Rodón. Props to paying Marcus Stroman. But both of those moves were overdue (and are still not even that satisfying) for all the pitching whiffs in previous seasons. The past is the past, but it still applies to our future analysis. So when Cashman revealed what happened in the Flaherty talks with the Tigers, fans rightfully lost their minds.

Why are we hell bent on "matching up values" when you badly need to improve you pitching staff? We totally understand not committing a massive overpay for two months of a player with potential back issues, but if you were gunshy about out-doing the Dodgers' weak offer, then it's clear there is zero willingness to go beyond what the front office feels is right. And that stubbornness has and will continue to hold the Yankees back in trade negotiations.

It's not all about the value "matching." It's about getting a player you need and throwing (some) caution to the wind, knowing that you'll be better off in October of an all-important year rather than worrying about looking a tad foolish when the dust settles next April.

The Yankees are supposed to be cutthroat. Not scared and hesitant. That's what's been wrong with this team since 2018. Cashman had an awesome trade deadline in 2017 and hasn't even come close to replicating that during the team's most promising championship window. Steps backward, over and over.