While there’s plenty of speculation as to what (if anything) the Pittsburgh Pirates will do at the upcoming trade deadline, general manager Ben Cherington is facing the prospect of his best chance yet to snap the postseason drought in Pittsburgh slip through his fingers.

After salvaging the third game of the team’s Yinzerpalooza series at PNC Park, the Pirates are now 54-52 with just one week before the trade deadline. Having constructed one of the best offenses in baseball (save for a few maddening performances here and there), his attention must turn to an abysmal bullpen who threatens night in and night out to hand away the game, and eventually, the season.

Only one other time in his tenure as general manager, which began after the house in the wake of the 2019 season, has Cherington “bought” at the trade deadline. And with the Pirates in the exact same spot they were in two years ago, 54-52 and with a chance at the playoffs, now’s a good time to re-visit the buyer version of Cherington.

Unlike this year’s team, who has pretty clearly defined strengths and weaknesses, the 2024 team needed a little more help in several areas.

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