Rival executive dishes on Yankees' broken trade deadline strategy after underwhelming move

The New York Yankees made one trade. For a rental. In 2023.
Chicago White Sox v Atlanta Braves
Chicago White Sox v Atlanta Braves / Kevin C. Cox/GettyImages

With a chance to reshape their wildly uncompetitive roster with one of the worst offenses in baseball -- or, at least, the chance to take a massive swing -- Yankees GM Brian Cashman spent nearly all of Tuesday silent before uncorking a singular trade at 5:57 PM EST.

The trade deadline? Thanks for asking. It's 6:00 PM EST.

That deal was for rental reliever Keynan Middleton of the Chicago White Sox, a firebreather (cool) who wears No. 99 (not helpful) and has a gigantic beard (neat). Middleton, a reclamation project in Chicago, has parlayed elite fastball spin and an exceptional chase rate into an interesting season at the back end of the White Sox bullpen. He is not under contract beyond this year.

It cost the Yankees Juan Carela, per Joe LoGrippo, who's been a relatively impactful starter with High-A Hudson Valley, striking out 109 men in 83.1 innings pitched this season. That's not nothing.

As Erik Boland noted, a scout called Middleton a "decent addition" but not a "difference maker". He was also ... the Yankees' entire trade deadline. In a season where so much, on so many levels, could've been done.

Yankees Trade Deadline Grades: INCOMPLETE (Irrelevant) for Keynan Middleton, and That's It

Keynan Middleton will not be extended. Keynan Middleton will not be closing games. Keynan Middleton will probably not be thought of again in the Bronx after 2023, except as a signifier of the dullest deadline in franchise history.

Harrison Bader wasn't in Tuesday night's lineup, but wasn't ultimately traded. Same with Giancarlo Stanton. Isiah Kiner-Falefa, who spoke out about the team's underwhelming season leaving everyone stuck in the middle, stays as well. Wandy Peralta stays. Luis Severino stays. Keynan Middleton joins.

As Marc Carig of The Athletic noted, one rival executive found himself frustrated by the way the Yankees handled their rentals this summer, proving once and for all that they're directionless.

Taking a massive swing would've represented (perhaps unfounded) belief in this roster. According to Brendan Kuty, the Yankees awarded their top scout with a trip to San Diego to scout the non-selling Padres in the nonexistent Juan Soto chase.

Selling off parts would've represented a reset, a fresh start, and the possibility of tripping into accidental success in the second half.

Keynan Middleton? He represents the worst thing of all: Brian Cashman's stasis. He wanted to hide today, because he knew it could work. And he succeeded at that, while failing otherwise.

Oh, wait! The Yankees traded for minor-league pitcher Spencer Howard of the Texas Rangers. That'll fix it.