Philadelphia Phillies: The 10 worst trades in franchise history

National Baseball Hall of Fame Induction Ceremony
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Phillies Trade Scott Rolen

This is another tough one because the Phillies had their hands forced when Rolen demanded a trade from the struggling Phillies despite them offering him a pretty significant contract. However, Rolen’s mind was made up and the package that Philly ultimately settled on was one that sent him along with Doug Nickle to the Cardinals for Placido Polanco, Bud Smith, and Mike Timlin.

Smith was supposed to be the centerpiece of the trade, but was a bust for the Phillies as a prospect. Polanco was a pleasant surprise and had two different productive stints in Philadelphia. Unfortunately for Philly, Rolen would play in four All-Star games with St. Louis and would be rewarded for an awesome 17 year career where he was a consistent hitter and amazing defender by finally getting elected to the Hall of Fame this year.

Phillies Trade Curt Schilling

Again, another situation where the player wanted out because he wanted to play for a contending team which didn’t exactly help the Phillies in the leverage department. Curt Schilling was a very good pitcher with the Phillies for north of a decade and was coming off three straight All-Star appearances before the Phillies traded him to the Diamondbacks for Travis Lee, Vicente Padilla, Omar Daal, and Nelson Figueroa back in 2000.

Most deals for a guy that has a borderline Hall of Fame resume are going to look particularly great, but the return for Philly was pretty brutal in this one. Padilla was the highlight and he was decidedly medium during his time in Philadelphia. Daal, Lee, and Figueroa were all out of Philly a couple seasons later. As for Schilling, he would become a perennial Cy Young contender and All-Star with Arizona and Boston after he left Philly before becoming one of the more polarizing figures in baseball during his post-playing career.