3 Yankees trade deadline mistakes Brian Cashman will regret

New York Yankees general manager Brian Cashman left a lot to be desired after a lackluster trade deadline showing. Yankees fans had plenty of hope that this season would be the year that New York would go all in at the deadline.

They began the week by acquiring Jazz Chisholm Jr. and then throwing their name in the rumors for a ton of different pieces like Tanner Scott and Jack Flaherty.

While Chisholm has looked great in Yankees pinstripes, New York didn't make an additional meaningful trade. Brian Cashman will likely have a few regrets about these last few days if the Yankees fall short of the World Series again.

(For more news and rumors, check out MLB Insider Robert Murray’s work on The Baseball Insiders podcast, and join the discord to get the inside scoop on the MLB trade deadline.)

3. Cashman will regret not adding more to the bullpen

The New York Yankees are notorious for having a strong bullpen. Strong bullpens are crucial for any team that's trying to make a real run at the World Series. Almost every contending team finds interest in acquiring relievers ahead of the deadline, yet the Yankees didn't really add an impact bullpen arm in 2024.

Aaron Boone has been forced to trot out borderline minor league arms for the entirety of the season and it doesn't look like Boone will have the fortune of choosing between elite arms at the end of games. Brian Cashman didn't acquire a high leverage reliever before the deadline passed.

Now, it's important to note that the market on bullpen arms was crazy expensive this year. New York would have been foolish to sell their farm to acquire an arm like Tanner Scott, who brought the Marlins three top six prospects from the Padres organization. But the fact that Cashman didn't look to add another back-end arm is concerning for the Yankees' 2024 World Series chances.

It's very hard to win a series in October if the bullpen isn't lights out. In short series' like the postseason, teams can't afford to give games away at the end of the game. Yankees fans are quite hopeful that they don't lose their season because their bullpen can't keep up.

2. Cashman will regret not replacing Gleyber Torres

It's very easy to look at the Yankees roster, stats or just to tune into a game and notice the gaping hole in the infield. Finding this gap is quite simple to do and it doesn't really take a genius to put the pieces together. But, Gleyber Torres has still been an okay hitter this year, so it wasn't really required that the Yankees make a move to replace him.

That was until the recent trade of Jazz Chisholm broke. And no, this has nothing to do with Chisholm and everything to do with the way Torres reacted. Jazz Chisholm responded by letting reporters, his coaches and his new teammates know that he was willing to play infield or outfield to help the team win. Torres responded by letting everybody know just how selfish he is. He stated that he wasn't going to play third base because he was a second baseman.

That kind of selfish attitude should have been enough for Cashman to look to replace him. Let alone including the fact that Torres has played like a fringe major leaguer at the plate with as many errors as anybody else at second all season long.

There weren't great infield options available, but New York should have gotten more involved in the market for infielders around the league.

1. Cashman will regret not adding a starting pitcher

The biggest current hole on the Yankees team is in the starting rotation. Their pitching rotation hasn't just struggled recently, but they have been incredibly bad. Even Gerrit Cole has struggled for the Yankees. Luis Gil, Nestor Cortes, Carlos Rodon and Marcus Stroman haven't been the pitchers that can lead a team to and through the playoffs either. It was very clear that New York needed to add a starting pitcher, no matter the caliber, before the deadline passed.

But somehow Brian Cashman messed that up and didn't land a starter. Cashman had the Yankees involved on a few different starters, with the most notable one being the Detroit Tigers right hander, Jack Flaherty. Flaherty would end up with the Dodgers in a trade that Los Angeles sent two prospects back to Detroit. It's laughable to think that Cashman couldn't have topped the offer that acquired Flaherty.

But Cashman sat on his hands, refusing to make a deal for one of the pieces that his team needed the most. Now the Bronx Bombers have to compete with teams that went all in at the deadline when they didn't do the same. They're going to watch as their competition welcomes in their new pitchers while they are forced to trot out the same arms that have struggled for quite a while now.