Brian Cashman
(Photo by Michael Reaves/Getty Images)

The Yankees continued their quietly effective offseason with new pitcher Marcus Stroman’s virtual press conference on Thursday. As far as intro pressers go, everything went as expected Stroman, who recently signed a two-year deal with the Yankees, mentioned how excited he was to compete on Yankee Stadium’s grand stage.

“I’m always up for a challenge, he said. “I think were capable of definitely having a deep October run.”

Stroman also complimented new outfield slugger Juan Soto, and general manager Brian Cashman then took questions. The same Cashman who said Stroman wasn’t a “difference-maker” during trade talks with Toronto in 2019. Stroman was eventually traded to the Mets and then moved onto the Cubs, but he’s insisted all is good.

“Me and Cashman kind of hashed out whatever it was that we had from a few years ago,” Stroman added. “We kind of laughed about it, and we moved on.”

And when it was his turn, Cashman was uncontroversial and par for the course as usual. All in all, he just gave updates on what the team was up to in the offseason. Essentially, Carlos Rodon is already working out at the team’s complex down in Tampa and it’s expected he’ll be back in ace form after an injury-riddled 2023.

Cashman also played the usual greatest hit: Giancarlo Stanton is in great shape, finally has his health under control, and “is in a really good place.”

To say the Yankees really need a strong season is becoming New York’s annual Understatement of the Year. The difference is that in 2024, the man and his methods and approaches to building a winner will be under the microscope. Perhaps more than he was at any point when George Steinbrenner was alive, too.

Going 82-80 again is simply not an option. Team captain Aaron Judge implied as much when calling for the front office to change its ways. The Yankees don’t just need to win in 2024, but win big. At least in the eyes of the players.

Cashman’s early results are promising. Adding the battle-tested Alex Verdugo to the outfield improved the lineup immediately without gambling on untested youth. Stroman has some injury risks, but is otherwise a solid groundball pitcher.

But on the other side of the coin, Cashman’s shrewd has also come off as stingy. The Yankees balked at giving Japanese ace Yoshinobu Yamamoto, now with the Dodgers, more than $300 million. Acquiring Soto is exciting, but he’s 25 and in his contract year, and the Yankees gave up a lot for him.

And thus is the vicious circle of the New York Yankees and Brian Cashman. His teams are competitive, but vanish in the playoffs. Injuries are always a problem. Social media loudmouths call for his head almost nonstop.

And yet, when it comes to the Yankees, it’s hard to trust someone more than Cashman. He re-signed Aaron Judge despite highly lucrative offers from the Giants and Padres.

Who was lying in wait for years, patiently counting down till free agency before finally adding Gerrit Cole, his admitted great white whale?

Say what you want about the man, but two things can be true about him. Brian Cashman can be a great executive with little to no objectively bad moves. Remember, he didn’t have this much power until about a decade ago.

He can also be someone who understands analytics, but hasn’t been the best at applying them. It’s like former Yankee Zack Britton said in a recent interview: The numbers are useful, but sometimes clash with what’s happening on the field.

Meanwhile, Cashman’s nearing the halfway point on his latest four-year contract. The Yankees’ World Series drought continues. Slowly but surely, the upcoming 2024 season is indeed shaping up to be a referendum on this New York front office.

We’ll soon see if the analytical executive pushed the right buttons.

Josh Benjamin has been a staff writer at ESNY since 2018. He has had opinions about everything, especially the Yankees and Knicks. He co-hosts the “Bleacher Creatures” podcast and is always looking for new pieces of sports history to uncover, usually with a Yankee Tavern chicken parm sub in hand.