Brian Cashman spoke to the media regarding both the Covenant House Sleep Out event, the 15th year he’s done this event, and about the Yankees as well.
Just days after Trent Grisham accepted his $22 million Qualifying Offer, the Yankees are preparing to continue navigating through their offseason plans, and Cashman provided some insight on the team’s perceived needs.
The budget remains a question for the organization, but Cashman revealed that the team remained engaged with agents about top-of-the market players such as Cody Bellinger and Kyle Tucker.
Discussing where the team is strong and where they’ve fallen short, Brian Cashman provided candid answers to a variety of questions regarding the state of the roster.
READ MORE: Yankees’ Brian Cashman suggests the lineup needs one new catalyst
The Yankees Believe in Trent Grisham’s 2025 Breakout
On Tuesday, the Yankees found out that Trent Grisham had accepted the $22.025 million Qualifying Offer they extended him, sparking discourse online about this outcome.
It sparked me to ask Brian Cashman not about whether he was shocked to see Grisham come back or not as fair or not, no one would even remotely think that he’d reveal their concerns if they were privately stunned at his return.
Instead, I asked the Yankees’ long-time GM about why the team felt he was worthy of the $22.025 million offer in the first place, one they chose to make before knowing whether he’d take it or not.
“He had a very impactful season for us hitting leadoff and playing centerfield…we believe the changes he made are real.”
The reason I asked about the team’s evaluation of Trent Grisham rather than about the team’s internal opinion about whether they did or did not plan for him to return is because I can weigh the former against public data.
FanGraphs, ESPN, CBS Sports, and The Athletic all did MLB Free Agent big boards, and his average placing on that list was 17th overall, but all three had him as their third-best outfielder.
Brian Cashman’s claim in that video about Trent Grisham being the third-best outfielder in free agency is one that was shared among baseball’s top writers, but what do the numbers tell us?
Grisham was tied with Harrison Bader for the third-most WAR produced by an outfielder on the market (3.2), and FanGraphs projects him to produce the third-most WAR in 2026 among outfielders.
He’s projected for 2.7 WAR in 130 games ($8.2 million per WAR) which is the market value for WAR, meaning all of the Yankees’ internal models and evaluations are right in-line with the public evaluations.
With a .741 OPS and 110 wRC+ projected for him by FanGraphs, Trent Grisham is expected to regress but remain an effective hitter as he provides a solid bat to their offense.
How Will the Yankees Continue Building the 2026 Squad?
Brian Cashman noted that Cody Bellinger is still among the team’s top priorities, and he hinted at the team needing multiple outfielders this offseason.
In the same segment discussing Trent Grisham, he said the Yankees had ‘two vacancies’ in the outfield when free agency began, and this raised some eyebrows as he repeated that multiple times throughout the night.
Sources told Empire Sports Media in late-October that the team made numerous efforts to trade Jasson Dominguez, not to just get them off their hands but to cash-in on his value knowing they didn’t have a clear path for playing time.
It was interesting to hear Brian Cashman refer to their outfield as Judge, Grisham, and then a battle of Jones and Dominguez for left field.
He also noted the Jones-Dominguez battle for left field as a worst-case scenario and fallback option if the team was unable to add another outfielder.
To not name Dominguez the starter in left field and to open the door for Spencer Jones to take his job is quite interesting.
How the Yankees choose to solve their outfield issues remain to be seen, but that wasn’t the only offense needs the team believes it needs, with right-handed hitting and bottom-of-the-order contact at the forefront.
Paul Goldschmidt and Amed Rosario were big pieces on the Yankees’ bench in the postseason against left-handed pitching, and both are now on the free agent market.
The Yankees did speak with Goldschmidt’s agent about the future Hall of Fame first baseman, and Jon Heyman of the New York Post reported that the team has interest in retaining Rosario.
As for the strikeouts, Austin Wells (26.3%), Anthony Volpe (25.2%), and Ryan McMahon (32.3%) all saw increases in their strikeout rates from 2024 to 2025, indicating that they could reduce their 2025 totals for the following season.
Cashman noted that the team could import hitters with better contact abilites alongside mentioning that it could be corrected by internal development, which isn’t an unrealistic belief.
Wells specifically chased way more in 2025 compared to 2024, and more selective swinging could result in a lower strikeout rate for the 2026 season.
Pitching is another area where the team wants to make improvements, as Brian Cashman noted their big losses in the bullpen with Luke Weaver and Devin Williams being free agents.
He also brought up the starting rotation as an area of need if the team can match on value in the market, and we reported that Tatsuya Imai was a target they were expected to aggressively pursue.
Whether that changes because of Trent Grisham’s return or not remains to be seen, but Brian Cashman will have another busy offseason as he tries to reconstruct the roster for 2026.
Why Does Brian Cashman Sleep Outside Every Year?
An image such as the one above this text will probably be sent to your family group chats when one of Kyle Tucker or Cody Bellinger sign elsewhere.
Every winter, a new version of Brian Cashman sleeping outside is used in jokes to poke fun at the team’s activity (or lack thereof), and the Yankees’ GM himself admitted to seeing these memes online while the photos were taken.
He butchered the pronounciation of meme, but the point of this event isn’t to feed fans with materials for their rage-induced online posts, instead its an event done by Covenant House annually.
The nonprofit organization aims to provide shelter and support for young people facing homelessness, and Brian Cashman has been on their Board of Directors for years.
When I asked about how this event and cause provides him perspective on life, here’s what he had to say:
It’s become too difficult a part of life that you assume should not be the case…Covenant House is providing tons of services from housing, three meals a day, education, teaching them how to put together a resume, mental health programs…things we take for granted. I was born into things I take for granted.
This event has helped bring awareness to the cause and attention towards the Covenant House, who aims to help end the housing crisis that has affected young people at alarmingly high rates.
The National Conference of State Legislatures estimates that over 4 million Americans experience youth homelessness at least once a year, and its why Brian Cashman will sleep outside every November.
He’s done it through below-freezing temperatures, snow, and warm-wet conditions in New York City, but this year the weather was more run-of-the-mill for late-November.
An event that was inspired by sleepouts performed in Australia to raise awareness about homelessness has been adapted by the Covenant House, and it’s garnered a healthy amount of publicity every year.
Videos of the Yankees’ GM entering a sleeping bag might just be a meme to some, but the virality of it has motivated Cashman to continue doing it, as it brings more attention and awareness to youth homelessness.