
No. 1: Trading Cliff Lee to the Mariners
One of the best trades Ruben Amaro made as Phillies GM was trading for Roy Halladay. The worst he made came just after, when he traded Cliff Lee to the Mariners for a trio of players that never worked out in Tyson Gillies, Phillippe Amount, and J.C. Ramirez.
Gillies never even reached the major-leagues, while Ramirez pitched just one uninspiring year in the majors with the Phils before being granted free agency. Aumont made 46 appearances over four seasons, managing a 6.80 ERA and 1.992 WHIP.
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Altogether, the team received -1.3 wins above replacement from the players received in the trade. Not to mention, Lee racked up 4.8 wins above replacement in 2010. It was pretty clear that Amaro knew he messed up when he signed Lee that next offseason.