The New York Yankees entered the trade deadline with many questions and somehow left with more. The Yankees — the last place Yankees — made two minor trades at the deadline, picking up relievers Keynan Middleton and Spencer Howard in separate deals, and that’s it. They neither bought nor sold, and they didn’t address their season-long left field problem either.
“We’re in it to win it. We stayed the course because of that,” GM Brian Cashman said after the trade deadline. “This was the best play for us with the team we have, still within striking distance.”
With all due respect to Middleton and Howard, the front office essentially did nothing at the deadline. The Yankees had two possible paths — go all-in and try to make the postseason or step back and focus on 2024 and beyond — and they chose neither, which is the worst possible thing they could have done. They marginally improved the 2023 team (but not their bottom tier offense) and solved zero problems for the future.
And those problems are numerous. The Yankees are three years into their search for a competent left fielder. Veteran stalwarts DJ LeMahieu, Anthony Rizzo, and Giancarlo Stanton have struggled mightily (LeMahieu and Stanton haven’t hit much for a full year now). The rotation behind the great Gerrit Cole is shaky and injury-plagued, and the bullpen is overworked as a result.
The Yankees insist they believe in their players and expect them to turn it around. They insist LeMahieu and Stanton and Rizzo will get going because their track records are so good. They insist passing on all those top free agent shortstops was smart because Anthony Volpe will be a star. They insist their next wave of prospects (Jasson Domínguez, Everson Pereira, etc.) will make an impact. All the answers are right there, they say.
The trade deadline makes you wonder whether anyone upstairs, specifically Cashman and owner Hal Steinbrenner, has a grasp on reality and the team’s current situation. Are they honest with their self-evaluation? Do they understand they have an aging roster and have struggled to finish off the development of their young players at the MLB level, or that the other four teams in the AL East are on the rise? They’re so sure of themselves even though the team on the field inspires no confidence.
“They’re professionals, obviously they’re extremely talented,” Cashman said of his struggling veterans. “Hopefully they’re saving their best baseball for the last two months.”
For lack of a better word, the Yankees are complacent. Complacent and delusional. They’re similar to the Dallas Cowboys in that they’re still coasting off a long ago dynasty — the late 1990s were a great time for New York baseball — while the rest of MLB passes them by. The Yankees aren’t bad (55-51 entering Tuesday) but they’re not good either. I’m not sure they know that.
And the thing is, the Yankees have shown some sense of urgency this month.— it was the first time since 1995 they fired a coach in-season — and they brought captain Aaron Judge back from the injured list without a proper minor league rehab assignment this past weekend. He’s playing on a torn toe ligament and is expected to have surgery after the season.
How can you fire your hitting coach and let your franchise player play on an injured toe in Year 1 of a nine-year contract and then sit on your hands on the deadline? Middleton’s a nice reliever who will protect a few leads down the stretch and the Yankees have had success helping talented pitchers like Howard level up, particularly as relievers, but those two only move the needle so much, and they address zero pressing roster needs.
“You’d rather be in a more defined spot,” Cashman said, defining Yankees as “cautious buyers.”
The Yankees can’t seem to pick a lane. Firing Lawson and bringing Judge back early suggests they want to win and want to get to the postseason, yet their trade deadline inactivity says they don’t consider this team worth a more significant investment. It’s on the players already on the team to figure things out even though evidence has been mounting that there is no figuring it out. This is who they are, and what they are isn’t good enough.
Entering Tuesday, the Yankees were 3.5 games behind the third wild-card spot, and there’s still plenty of season remaining. Why can’t they go on a run and make the postseason? The front office gave the players little help at the deadline though, nor did they do anything to make the team better next year. There is no discernible plan in place. The Yankees are neither all-in nor all-out. They’re in the middle, and that’s how you get left behind.