Keith still laments Yankees not doing more at trade deadline in all-in season

As the Yankees resume action against the Guardians on Tuesday night, Keith took Monday’s show to assess where the Bombers stand with six weeks to go in the season, and the areas of concern throughout the roster.

Keith has concerns about the lineup outside of Juan Soto and Aaron Judge, and big issues with the bullpen and Clay Holmes, which leads him to wonder why Brian Cashman didn’t do more at the deadline, the team’s last chance to upgrade the roster before an October push.

“You’re not doing this in Milwaukee or Arizona. You’re doing it in New York with the Yankees and this fanbase and all the resources that they have,” Keith said. “He himself said ‘If you don’t hoist that trophy up at the end of the year, it’s a failure.’ So knowing that, Cash, why don’t you do more? That’s where I’m lost.”

The Yankees made a big move to acquire Jazz Chisholm before the deadline, but on deadline day, the only moves were for relievers Mark Leiter Jr., who has struggled mightily since the trade, and Enyel De Los Santos, who the Yanks cut ties with shortly after acquiring due to inefficiency.

For a team that is supposedly all in, in a league that seems as wide open as ever, Keith said more had to be done.

“My hands were up in the air. I’m like, ‘That’s it? That’s it for this year, which could be one year of Juan Soto and Aaron Judge can win the MVP again? That’s it?’” Keith said, noting that the organization had the resources in the minors to make bigger deals. “The Yankees have a bunch of top prospects and everyone knows their names. You’ve seen them. They just won’t detach from them. They’re playing the long game. I understand planning for the future, but you need to strike right now.”