Danny Duffy Disaster
This one really deserves its own longer look, or potentially its own category on this list. While the Gallo trade was odd because of a lack of potential fit and lackluster production with the Dodgers, the Danny Duffy trade completely redefines all of that.
Near the 2021 trade deadline, the Dodgers acquired Duffy and cash from the Royals in exchange for a PTBNL, which ended up being RHP Zach Willeman. Before getting to Duffy, it's important to note that Willeman struggled in the Royals organization at both Double- and Triple-A, eventually leading to his release from the team. He then signed a minor-league deal with the Marlins, and is at Double-A right now.
So, how could I rank this as the third-worst trade in the Andrew Friedman era if the player the Dodgers gave up basically nothing? Well, because the Dodgers basically got nothing in return. Actually, worse! The Dodgers had to pay Duffy $5 million of his remaining salary in 2021, only for him to appear in just as many major league games as Willeman did for the Dodgers.
If you don't understand what that means, Duffy never took the mound as a Dodger in 2021. Even after he didn't pitch in 2021, the Dodgers re-signed him for $3 million before the 2022 season. In 2022, he was sent on a rehab assignment in late August, then he made it to Triple-A OKC, but once again failed to make a major league appearance. All things told, the Dodgers gave Duffy $8 million and the Royals a minor-league pitcher for zero total innings pitched. But I'm here to tell you this trade is somehow not the worst of the Friedman era for the Dodgers.