Pressure Starting to Mount for Yankees' Brian Cashman

No one cares about the pinstripes more than New York Yankees general manager Brian Cashman. After all, he's been with the organization more than 30 years and has run the club's front office since 1998.

There's no doubting Cashman's Hall of Fame resume, which includes the most recent Yankees dynasty that produced four World Series titles in five seasons. Cashman added another ring in 2009 and built a roster that returned to the Fall Classic in 2024.

But that's exactly the problem. It's been 17 years since the Yankees won the World Series. For fans in the Bronx, that's much too long to go without a victory parade through the Canyon of Heroes.

As a result, Cashman is one of the MLB executives facing the most pressure as the Aug. 3 trade deadline approaches.

Cashman under pressure

In fact, ESPN's Buster Olney ranks Cashman at No. 7 on his hot list.

"Assuming that Aaron Judge is effective once he comes back from a stress fracture to his rib, there will be a lot to like about the Yankees, with their strong rotation and deep lineup," Olney wrote. "But the bullpen will likely undergo a makeover at the trade deadline, with a clear need for a couple of power arms.

"Maybe Ryan Weathers will go, but Cashman might also have to deal for one of the better relievers available -- as well as a right-handed hitter, such as Twins catcher (Ryan) Jeffers," Olney adds.

Ready to wheel and deal

Cashman annually is among the busiest of execs ahead of the MLB trade deadline. In addition to a crisis at catcher, the Yankees could use more high-leverage bullpen arms and a solution to the production problems on the left side of the infield.

But Cashman won't be alone in looking to wheel and deal, with some executives trying to make trades to save their jobs, including Boston Red Sox chief baseball officer Craig Breslow, who comes in at No. 3 on the list.

Tigers president of baseball operations Scott Harris tops Olney's list, and with good reason, as Detroit ponders trading two-time American League Cy Young Award winner Tarik Skubal, with the Yankees mentioned as a potential suitor.

The crosstown Mets also face a leadership decision, with president of baseball operations David Stearns checking in at No. 2 on Olney's list as he tries to fix an expensive and under-producing roster in Queens.

As for the Yankees, its World Series or bust in the Bronx, and no one knows that better than Cashman. FanGraphs gives New York a 15.1% chance of winning it all this year. Only the Los Angeles Dodgers (23.3%) have better odds.

But if 2026 ends without a World Series celebration, owner Hal Steinbrenner has to decide if fresh blood in the front office is needed to get the club over the hump and end the title drought.

This article was originally published on www.si.com/mlb/yankees/onsi as Pressure Starting to Mount for Yankees' Brian Cashman.

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This story was originally published June 17, 2026 at 6:36 AM.