Yankees entering precarious trade deadline territory with too many roster holes again

The longer you wait, the harder it gets. With the newly expanded playoff field MLB instituted a few years ago, the trade deadline has become more difficult to navigate as teams wait it out before waving the white flag and becoming sellers. But the New York Yankees haven't exactly adapted.

In yet another year of contention (but doing so with an obviously flawed and incomplete roster), the Yankees are taking it down to the buzzer before making any additions via trade. Again, it's not all on them, but if the Kansas City Royals can get ahead of the action, so can Brian Cashman and Co.

Over the weekend, Kansas City improved its bullpen by acquiring reliever Hunter Harvey from the Washington Nationals, who was going to be among the sought-after arms as we got closer to July 30. Much like last year when the Texas Rangers acquired Aroldis Chapman, this is yet another example of another team thinking ahead and being aggressive.

The Yankees are already at a disadvantage. Teams don't want to trade with them, and if they do, they raise the asking price. It's just the cost of doing business. We'd do the same if we were another front office.

But Cashman and Co. continue to act with the same intention as the results get worse. In 2020, they did nothing. In 2021, they jumped the line to trade for Joey Gallo, who was an all-time bust. They also acquired Anthony Rizzo and Andrew Heaney. Rizzo was fine. Heaney was bad. Another failed deadline. In 2022, Cashman ruined everything, shipping Jordan Montgomery to the Cardinals for Walking Boot Harrison Bader, which upended team chemistry. He also acquired Frankie Montas (injured), Scott Effross (injured), Lou Trivino (injured) and Clayton Beeter (injured now, but better than keeping Gallo).

Last year, it was Keynan Middleton. We were told that was it, and we'd have to enjoy it.

Yankees entering precarious trade deadline territory with too many roster holes again

So what's the plan this year, Cash? Wait until the last moment yet again when you have needs at second base, third base and catcher? When the starting rotation and bullpen need support/depth? How many trades do you plan to make in a matter of hours? Because the more you cram, the less you'll actually get done.

The Yankees' rosters of the last four years were very much limping and in need of more once June arrived, and the front office sat back, fueled by misguided patience and the stale belief that the return of injured players would help the team "turn a corner." Not this time. That's not the case.

Though injuries have held the Yankees back this year — just like they do every year with every other team — we'd argue they've probably had their best luck on that front in 2024 compared to 2019-2023.

The nonsense has already started. The Chicago White Sox reportedly want Spencer Jones in any deal involving Garrett Crochet, who might not even be able to finish the season as a starting pitcher as he surpasses his career high in innings pitched. Think the negotiations will get easier from this point? The White Sox have been out of it since Day 1 and they're not budging two weeks before the deadline.

For teams that are on the fence about selling and parting with assets, it's going to be a tougher bargain. We're just hoping the Yankees don't learn the hard way yet again, because this time it might influence the departure of one of the best players in baseball.