Pirates insider hints Ben Cherington has surprising trade deadline plan of attack

The Pirates have a big trade deadline approaching. While it doesn't feel like last year, where they attempted to put the finishing touches onto a postseason roster, this deadline must move them towards building a contender for 2026. While this will nominally involve selling players on expiring deals (and possibly controllable players, too), Pirates play-by-play man Greg Brown stated on a radio show this week that he believes Ben Cherington is thinking of acquiring "something big" at the deadline, pairing a sell-off with a controllable addition.

Brown recently spoke to Cherington on Sunday via a radio show on 93.7 The Fan. Brown once again was on that station on Tuesday and said, based on their interview, he believes that Cherington may have something brewing.

"On a move that would make them like a buyer you mean?" Brown was asked.

"In essence, yes," he replied.

The idea of the Pirates acquiring rentals was also shut down. That really went without saying, of course, as the Pirates sit 16 games back of .500, but Brown made sure to make it abundantly clear when describing what kind of deal he believes is in the works.

Greg Brown believes that Ben Cherington is going to make a big move soon to add to the Pirates' roster ahead of the MLB Trade Deadline.

Cherington buying a player at this deadline would be bold and could honestly save him his job. This season has put him on the hot seat, and Derek Shelton was already used as a scapegoat. Even while Don Kelly has done well as the manager, key roster flaws have continued to glow, showing how Shelton may have not been the ultimate problem.

Adding a controllable player could help the team avoid the 90-loss plateau. Getting over 76 wins on the year would be a slight improvement from 2024, and doing so would require an over-.500 performance for the rest of the season. The Pirates have seven players on expiring deal sthat they'd like to deal at the deadline to get something before losing them to free agency, which would make it more difficult to achieve that win total.

An aggressive move like the one Brown hinted at could help the team improve while selling. Even though it won't push them to a postseason bid, it could make the roster better for 2026 and beyond.

A trade like this is hard to project, considering a young and controllable player would have to be involved. A dream would be to deal a guy like Mike Burrows or Braxton Ashcraft to Boston for Wilyer Abreu. Something along those lines would get Pittsburgh a bat to build around, while utilizing this surplus of talent they've built in the pitching staff.

A trade like the one described above would be very exciting for this organization. Hopefully Cherington is truly working on a job-shifting deal to help boost this team's playoff chances in 2026. Money in free agency will be hard to come by as is, so this may be the only way to get legitimate pieces.