Brian Cashman’s refusal to sell is haunting the Yankees

Move over, Shakespeare, because the Yankees’ 2023 season is becoming more comedic than Theseus and Hippolyta’s wedding in A Midsummer Night’s Dream. By July, it was clear this team had no identity, no fight, and no urgency. They sank like a rock before the dog days, claiming sole possession of last place in the AL East by the All-Star break while the Orioles, Rays, Blue Jays, and even the overlooked Red Sox all played respectable baseball. Perhaps most insultingly, owner Hal Steinbrenner gaslighted the fanbase when 2023 started to go awry in earnest. He proverbially threw up his hands, conjuring patronizing befuddlement at fans’ justified frustration. He and Brian Cashman’s crippling hubris have plunged the team into mediocrity for the foreseeable future, but it wasn’t always this way.

In 2016, the Yankees finished 84-78, but the season was far from a lost cause. Cashman convinced Steinbrenner that his team was not strong enough to win the 2016 World Series at the Trade Deadline, a bitter pill to swallow but the right call long-term. Although they did have some strengths, it had grown oh-so-apparent that their core was not going to be nearly enough to do the job. The Yankees retooled by trading away key pieces on soon-to-expire contracts and the next year, they found themselves with another Baby Bomber boom and on the doorstep of the 2017 World Series.

Andrew Miller was shipped off to Cleveland and Aroldis Chapman went to the Cubs at the 2016 deadline. (Veteran masher Carlos Beltrán was sent out to Texas, too.) Both Miller and Chapman ended up playing in the 2016 World Series, but more importantly, the return was a king’s ransom of prospects, including top name Gleyber Torres. Half a season of a relief pitcher, even an excellent one, just isn’t worth that much, but Cashman lined up a great deal for Chapman with the championship-starved Cubs desperate to parlay their value. Miller had a year and a half remaining, and Cashman got what was then widely perceived as a very nice prospect package for the southpaw from a Cleveland team that hasn’t won it all since 1948.

Putting together the relief corps was Cashman’s ballyhooed offseason maneuver and the envy of the baseball world in April, but he realized that even an elite bullpen wouldn’t give that 2016 team a chance. Elite bullpens very rarely vault an iffy team over the top — it’s just too small a piece of the equation. Seven years later, Cashman has lost the ability to identify a sinking ship as such, and Steinbrenner, ever the delegator, followed his lead. Essentially, the GM doesn’t have the humility any longer to truly admit fault as he did in 2016, and the owner isn’t exactly doling out consequences like his father did. Cashman can say what he wants to the papers about the state of the team writ large, but actions speak louder than words.

Now, let’s be clear. There’s no Betances/Miller/Chapman brilliance in this bullpen on expiring contracts. And the market may not be as desperate as it was back in those days to float major prospects just to acquire a minute edge. However, the Yankees have the best bullpen ERA in the MLB. A last-place team — one that was only technically in the Wild Card mix with multiple teams in front of them anyway — has no short-term use for such luxuries, especially ones hitting the free agent market this winter.

Playoff teams always need effective left-handed relievers to go up against the Freddie Freemans and the Kyle Tuckers of the world. The Yankees acquired Wandy Peralta in 2021 and proceeded to shape him into a bullpen option capable of executing the toughest left-on-left assignments. Now, he very well may walk. Peralta’s skill set makes him enticing and his price will go up significantly as a free agent this offseason. Lefties hit .108 off Peralta this year, and his changeup-sinker combo keeps the ball on the ground. That’s a slam-dunk addition for a team in win-now mode.

By way of comparison, the Dodgers acquired rental lefty Ryan Yarbrough from the Royals for an upper-minors prospect and a teenage international signing lottery ticket. After graduating or dealing most of their top-30 for complete whiffs like Frankie Montas, the Yankees stand to benefit much more from a lottery ticket than half a season of lefty-lefty matchups. The same logic applies to high-leverage arms Clay Holmes and Tommy Kahnle. They were lesser versions of 2016 Miller, as they’re signed through next year, but once again, Cashman not to sell from a strength with only so much utility. No relievers were traded.

The Yankees have done themselves no favors when constructing this lineup, and for all its faults it is an expensive one as well. They shelled out the big bucks to sign Gerrit Cole and retain Aaron Judge and both of those moves are prudent, but so much more is tied down to players who likely wouldn’t be starting anymore if they weren’t such albatrosses. Add onto that the ages of the players and it makes a fire sale next to impossible, even when that may be the most beneficial option, but there’s still plenty of wiggle room between there and riding the fence. A small return is still a positive return when the writing is on the wall should you ride the course.

The luxury tax threshold doesn’t matter when the financial and strategic decisions are so dire. After this year’s trade deadline, a far cry from 2016, the Yankees are no richer in prospects. Peralta will finish the season likely with continued excellence against lefties on a doomed last-place team. The offense will continue to sputter and stop randomly for the last month and a half of the schedule. And we’ll be left wondering down the line how this wasteful commitment to seeing a sinking ship down will have impacted the future of the team.