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6. The Andrew Chafin trade
After acquiring iconic reliever Andrew Chafin at the 2020 trade deadline, the Cubs cashed in on his low 2 ERA the following year. In exchange, the Cubs received pitcher Daniel Palencia and outfielder Greg Deichmann. Although Deichmann has been released and since gone back to the Athletics, Palencia has become one of the most promising arms in the Cubs' system.
Palencia is ranked as the 13th-best prospect in the Cubs system thanks to his highly touted fastball. Palencia recently made his MLB debut and he has thrown five innings so far. Even if his time on the roster in 2023 is limited, Palencia is destined to be a high-leverage reliever for the Cubs in the near future.
Although Chafin was a fan-favorite and a very good lefty reliever out of the pen, Palencia's upside made this deal a clear win for the Cubs.
Athletics get: LHP Andrew Chafin
Cubs get: RHP Daniel Palencia and OF Greg Deichmann