Things go from bad to worse for this recent Yankees trade deadline acquisition.

The New York Yankees were active at the trade deadline, making three significant moves to bolster their chances of a deep postseason run.

Among their key acquisitions were Jazz Chisholm Jr. and Mark Leiter Jr., but they also completed a minor trade with the San Diego Padres to add bullpen depth by acquiring Enyel De Los Santos.

The move was somewhat surprising given that De Los Santos had a 4.46 ERA in 44 appearances for the Padres. However, Yankees GM Brian Cashman is known for his ability to identify undervalued relievers and develop them into key contributors under pitching coach Matt Blake.

Unfortunately, De Los Santos didn’t become one of those success stories. He was designated for assignment just a few weeks after joining the Yankees and, to make matters worse, was claimed off waivers by the struggling Chicago White Sox, who have a dismal record of 30-93.

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Enyel De Los Santos’ season reaches new low following White Sox claim

Of all the teams that could have claimed De Los Santos, it’s fitting that it was the White Sox who did. His final appearance before being DFA’d was against the White Sox, where he allowed seven runs in just 1.2 innings during a lopsided loss. At that time, the White Sox had a record of 28-91.

On the one hand, this move could benefit De Los Santos, as he is likely to get plenty of pitching opportunities with a White Sox team that will be heavily reliant on its bullpen. On the other hand, playing for a team with a 30-93 record isn’t exactly a highlight of a player’s career.

This represents a significant setback for the 28-year-old De Los Santos, who had established himself as a reliable middle reliever with the Cleveland Guardians in 2022 and 2023. His strong performance led to a trade for Scott Barlow, another dependable reliever, during the offseason. However, his tenure with the Padres was underwhelming, and he allowed ten runs in 6.1 innings across five appearances with the Yankees. Now, he finds himself with the White Sox.

On the bright side, De Los Santos will likely be a trade candidate in the offseason as the White Sox continue their rebuilding process. Regardless of how he performs with this struggling team, his time in Chicago is expected to be brief.