Yankees rumors: Insider expects Brian Cashman to be ‘aggressive’ before trade deadline

The New York Yankees are in striking distance of the AL East, as the club is only 3.0 games behind the first-placed Tampa Bay Rays. With the MLB All-Star break in the rearview mirror and the second half of the regular season about to begin, rumors are heating up that general manager Brian Cashman could make some notable moves before the August 3 trade deadline.

At least that’s what ESPN’s Buster Olney believes. During a segment on “First Take” on Wednesday, Olney claimed that he expects Cashman to make aggressive moves to improve the roster. Those potential trade additions, along with Aaron Judge and Giancarlo Stanton eventually coming back from injury, could be what puts the Yankees over the edge to possibly go on a deep playoff run.

“Am I concerned about the Yankees winning the AL East? Absolutely, because Judge, Giancarlo Stanton, they’re not close to coming back,” Olney said. “But in terms of making the playoffs, and perhaps playing deep into October, I think they will still figure it out before the end of the year.

“Brian Cashman, their general manager, will be aggressive before the trade deadline,” Olney claimed. “Add a reliever, maybe a right-handed batter. And they will get Judge and Stanton back, and they will be a factor again in October.”

"In terms of making the playoffs, and perhaps playing deep into October, I think [the Yankees] will still figure it out before the end of the year." @Buster_ESPN on the concern for the Yankees without Aaron Judge pic.twitter.com/bGu6H0gmVV

— First Take (@FirstTake) July 15, 2026

Although Olney didn’t provide any names to keep an eye on as possible trade targets, he did narrow down the positions that Brian Cashman may prioritize. An improvement for the bullpen would be a smart add, as playoff teams tend to rely on the bullpen throughout the postseason. Also, adding a right-handed hitter to the lineup could improve the offense just enough before Judge and Stanton return.

While the playoffs are still a few months away, the one thing working in the Yankees’ favor, as Olney points out, is that the American League is not all that competitive this season. To put things in perspective, the club’s 54-42 record would be good enough to put them in first place in both the AL Central and AL West.

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