2. Adam Eaton
A former Phillies first-round pick, right-handed pitcher Adam Eaton was traded to the San Diego Padres before he could begin his big-league career in red pinstripes.
Eaton was mediocre at best in parts of a few seasons in San Diego — his best year being an 11-5 win-loss record season, where the Seattle, Washington, native recorded a 4.27 ERA. After a stop with the Texas Rangers, the Phillies decided to sign Eaton to a three-year deal worth around $24 million following the 2006 season.
It remains to be known if the Phillies saw something in the late stages of Eaton’s career, or were just misinformed enough to make the same mistake twice. Regardless of the decision-making process, Eaton would not perform up to expectations, if there were any. He only made through two seasons in his second Phillies organization stint, boasting a 6.10 ERA.
Eaton did strike out 154 batters, and it only took him 268 2/3 innings to do so. Oh, and in that same time period, Eaton walked 115. Not a recipe for success on the big-league mound.
3. David Robertson
The most recent failure on this list, the Phillies thought they were getting a late-game finisher when they signed 2009 World Series champion reliever David Robertson.
Instead, they got seven innings and a major surgery that left Robertson with question marks on the future of his big-league career. The injury is obviously not Robertson’s fault; it’s the investment made on the part of the organization that makes this a bust.
Before the Phillies recently executed the $2 million buyout clause in Robertson’s contract for the 2021 season, Robertson made $21 million between 2019-20. He would have made $12 million next season, had the Phillies exercised the team option.
The initial deal made a little bit of sense at the time, as there was no reason to believe Robertson was slowing down — given his effectiveness in a second stint with the Yankees (2017-18), appearing in nearly 100 games and striking out 142 in 104 2/3 innings.
Set to turn 36 in April, and amid an unprecedented free-agent market, it’s possible that Robertson will never be that player again — at least not in a Phils uniform.