Breaking down Brian Cashman’s end-of-season press conference

The Yankees are notorious for strategically weaving through questions asked by the media, whether it be in the locker room or at a press conference like the annual end-of-season presser that took place on Thursday. If you listen closely, Brian Cashman revealed a lot behind his thinking following the end of the 2019 season, and it says a lot for how he might approach the offseason.

Cashman left little crumbs of his philosophy toward the postseason throughout the press conference, noting that the Wild Card Nationals were on the cusp of a championship, which seemed improbable when the playoffs began. In the book ‘Inside the Empire,’ which was released earlier this year, Cashman’s belief of the postseason basically being a crapshoot was apparent. While there’s plenty of truth to that belief, Thursday’s press conference seemed to indicate that he would be doubling down on that mindset, again seeking to win the division and make the postseason rather than do everything possible to create the best roster in the league that would eliminate as much of October’s randomness as possible.

In the presser, Cashman raved about the pitching for the Yanks, and how it put the team in position to win the series. That’s absolutely true, but with options that could make that staff even better in 2020 (and by a large margin), Cashman seemed to set fans up for a winter of backing away from the big fish like Gerrit Cole.

The highlight of the presser came from WFAN’s Sweeny Murti, who posed a fair question to Cashman regarding top starters that the team has ‘passed on’ in recent years, like Justin Verlander, Max Scherzer and Patrick Corbin, all of whom are currently in the World Series. Cashman grew testy with Murti and insisted the Yanks didn’t pass on any of those arms, while also saying “I can sleep at night with the process we have in place and it’s served us well and given us a legitimate shot at a championship.”

It doesn’t take much to read into that and realize that Cashman and Hal Steinbrenner may simply not believe handing out a big contract to a Cole or Stephen Strasburg is necessary to winning a World Series. However, missing out on Verlander in 2017 arguably cost the Yanks at least two trips to the World Series, though Cashman stood by the team’s philosophy that going after him that summer would have meant blowing past a self-imposed financial cap, which the franchise clearly has no desire of moving past.

Add it all together, and you likely have a plan that doesn’t include Cole or Strasburg this winter. Cashman has taken the October crapshoot idea and is using it as a reason not to break the bank. Although the philosophy holds plenty of truth, it shouldn’t be used as a reason to pinch pennies, especially with an organization that boasts the financial might as the Yanks. By not opening the checkbook for an arm like Cole, or Verlander and Corbin in the past, the Yankees seem to be deliberately neglecting one of their biggest advantages over the rest of the league: money. They have a lot of it, but it doesn’t sound like it will be used on an ace starter.

When asked about potential bullpen fatigue down the stretch of the series, Cashman alluded to the loss of Domingo German and Dellin Betances, again insinuating that internal options could have changed the narrative of the ALCS. Perhaps they could have, but signing a star like Cole would help eliminate some of those ‘what ifs’ when it comes to chasing a title. Unfortunately, it doesn’t seem like the front office agrees. We’ll see if that changes come winter.