Ben Cherington's last Pirates buying spree makes deadline optimism impossible

The Pirates are entering the trade deadline in an unfamiliar position. Entering play on July 30 a mere two games out of a Wild Card spot and boasting a surprisingly potent offense, Pittsburgh has every incentive to buy and make a push for the postseason.

Unfortunately, Ben Cherington hasn’t had the best of luck adding at the deadline in the past.

The last time the Pirates were poised to make a run at October, their general manager added a batch of underwhelming players: Bryan De La Cruz, Isaiah Kiner-Falefa, and Jalen Beeks. The year was 2024, and the Pirates were 2 1/2 games out of a Wild Card spot. A second-half collapse saw them fall to 76-86, 13 games out of postseason contention.

Those three deadline pickups in 2024 combined for -0.8 bWAR in their time with the team. De La Cruz, whose bat and multiple years of team control were supposed to be his biggest selling points, wasn't even tendered a qualifying offer at the end of the season.

Needless to say, Cherington and the Pirates’ front office will have to do better this time around.

Ben Cherington and the Pirates are hoping for better results as trade deadline buyers in 2026

On the bright side, the 2026 version of the team is much stronger than the 2024 squad. The hitting is in the Top 5 in most categories, and the starting rotation boasts several dominant arms. The bullpen is where the whole thing falls apart. Cherington will have to do much better than a Jalen Beeks-esque reliever to bolster the ‘pen.

There are game-changing options here, such as the Padres’ Mason Miller, but Cherington doesn’t have the final say. Bob Nutting holds the purse strings, and he’s always loath to spend. Acquiring Miller would also probably cost the Pirates a top prospect or two or a controllable big leaguer such as Jared Jones. As much as Pittsburgh wants to improve at the deadline, this move may be too costly.

Another pitfall that Cherington may fall into that is reminiscent of the 2024 deadline is focusing too much on the future instead of trying to win now. Nick Yorke and Billy Cook both came to the club in that flurry of moves. They’re typical Pirates utility players, but to compete for a postseason berth, the Bucs need pure strength rather than versatility. They can't afford to let this round of "buying" look too similar to the last one.

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