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Clay Holmes' journey to the big leagues began when the Pittsburgh Pirates drafted him in 2011, bypassing a college baseball commitment at Auburn University. Holmes was given a significant signing bonus of $1.2 million to sign. After signing with the Pirates and enduring the rigors of the minor leagues, Holmes earned a spot on the Pirates' 40-man roster in 2016.

In his debut year, Holmes showcased promise with a solid outing against the Cincinnati Reds. However, his tenure with the Pirates was marked by fluctuations between the majors and minors. Despite setbacks like Tommy John Surgery in 2014, he would pitch in 91 total games for the organization. Ultimately in 2021, he would make 44 appearances for the Pirates during the 2021 season before being traded to the New York Yankees.

At the time, many fans of the Pirates were happy with the trade. The Bucs were able to land two of the Yankees' top 30 prospects for an erratic reliever who just could not figure it out. Coming back in the deal were infielders Hoy Park and Diego Castillo. Both are no longer with the Pirates organization. Meanwhile, Clay Holmes has turned in a 2.50 ERA over the last 2.5 seasons with the Yankees.