As the Pittsburgh Pirates enjoy a winning record at the All Star Break for the first time since 2016, all attention will soon turn to returning Buctober to PNC Park for the first time in over a decade.

Only once during the reign of general manager Ben Cherington have the Pirates “bought” at the trade deadline. That year, with the Pirates hovering right around .500 at the end of July, Cherington sent assets out to acquire infielder Isiah Kiner-Falefa from Toronto, outfielder Bryan De La Cruz from Miami, and reliever Jalen Beeks from Colorado.

Unfortunately for those Pirates, none of those additions proved pivotal. Kiner-Falefa and De La Cruz were weak offensively, the latter was a nightmare in right field, and Beeks was a middling arm at best.

Two years later, the Pirates find themselves in a similar position. Right around that .500 watermark and with a chance to try and make a serious run for the postseason, Cherington’s team is hoping to break the long-suffering playoff drought.

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