Getty

New York Yankees' executive Brian Cashman is under pressure ahead of the MLB Trade Deadline

The New York Yankees had Monday off after defeating the Toronto Blue Jays over the weekend.

They’re now returning home to Yankee Stadium to host the Chicago White Sox on Tuesday at 7:05 p.m. ET.

While New York’s organization continues navigating the season, the MLB Trade Deadline is nearing.

Yankees Predicted To Shake Up Their Bullpen

New York Yankees‘ Ryan Weathers could possibly be traded at the MLB Trade Deadline

According to baseball insider Buster Olney of ESPN, New York is expected to undergo a bullpen makeover at the 2026 MLB Trade Deadline.

Yankees’ executive Brian Cashman, alongside a handful of others, is under pressure as he considers his options.

As written by Olney, “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. But the bullpen will likely undergo a makeover at the trade deadline, with a clear need for a couple of power arms…”

Olney pointed out that 26-year-old pitcher Ryan Weathers could find himself on the chopping block.

However, he also wouldn’t be surprised to see New York go for “one of the better relievers available — as well as a right-handed hitter, such as Twins catcher Jeffers.”

In terms of ERA, the Yankees are ranked second in all of baseball at 3.32.

For strikeouts, they come in at No. 13 (600) and second in WHIP (1.18).

Bringing some fresh flamethrowers on board would only help.

This could ultimately be the key to pushing the historic ballclub back into the postseason.

New York’s 2026 Campaign

GettyNew York Yankees’ Ryan Weathers is a possible trade candidate at the MLB Trade Deadline

When the Yankees kicked off the regular season, they were a bit sluggish on all ends.

However, they reached a turning point and soon started to climb.

Looking at their placement in the standings ahead of their series against the White Sox, they currently lead the American League East 43-27 overall.

They managed to surpass the Tampa Bay Rays (41-28).

The Rays are ahead of the Blue Jays (34-38), the Baltimore Orioles (34-39) and the Boston Red Sox (29-40).

Things could always take a sour turn, but for now, the Yankees are looking quite steady among their opponents.

For the remainder of June, after hosting Chicago, New York will face the Cincinnati Reds, the Detroit Tigers, the Red Sox and the Tigers for a second time this month.

With the MLB Trade Deadline approaching on Aug. 3, organizations are under great pressure to set their ballclubs up for success as they aim for contention.

According to Olney, Cashman is one of the top executives facing the most pressure ahead of the deadline.

The top five executives in the hot seat are Scott Harris of Detroit, David Stearns of the New York Mets, Craig Breslow of the Red Sox, Jed Hoyer of the Chicago Cubs and Buster Posey of the San Francisco.

As for the Yankees, they have plenty going for them this season.

However, that doesn’t mean they’re all squared away.

There’s always an opportunity for enhancement.

The MLB Trade Deadline is the ideal time to capitalize on such opportunities and take healthy risks in the Major Leagues.