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Worst Trades in Phillies History

This article was written by our friend Johnny Goodtimes, author of Philly Sports History.

Ryne Sandberg

In the Hall of Fame with a Cubs hat.

With the trade deadline approaching, and as we all wait to see what Ruben is going to do, I thought we’d take a look back through the years at some trades that didn’t work out so well for the Phillies. Incredibly, this team has such a knack for terrible trades that 5-for-1 (Von Hayes was much better than Phillie fans give him credit for) and the Scott Rolen debacle (they got a young Placido Polanco and a solid Mike Timlin in return) don’t even crack the top 5.

#5. Freddy Garcia for Gio Gonzalez and Gavin Floyd. The Phils were looking for a front end of the rotation guy, and Pat Gillick apparently looked at Garcia’s 17 wins in 2006 more closely than he did his 4.53 ERA. He also must not have looked too closely at his right shoulder…after a 1-5 start, Garcia was finished. He made $10 million to earn one more win than I did in 2007.

#4. Grover Cleveland Alexander and Bill Killifer for Pickles Dillhoefer and Mike Prendegrast. Phillies ownership was, as usual, experiencing cash flow problems after the 1917 season. And so they let arguably the greatest pitcher in team history go for a catcher who batted .091 for his new squad and a pitcher who would be done in a year. Grover Cleveland would win another 183 games after leaving the Phillies.

#3. Curt Schilling for Travis Lee, Vicente Padilla, Omar Daal, and Nelson Figueroa. Listen, we all agree with Ed Wade that Schilling was a horse’s ass. Nonetheless, you would have thought a pitcher of his caliber would have brought more in return than the four mediocre journeymen they got. Not Ed Wade’s finest moment.

#2. Ferguson Jenkins for Larry Jackson and Bob Buhl. The Phillies were trying to recapture the magic that took them to the brink of the Series in 1964, and decided to trade a young reliever named Ferguson Jenkins for two wily old veterans. The key word was old. Jackson was actually serviceable as a starter, while Buhl was out of the league in a year. Jenkins went on to a Hall of Fame career, winning 284 career games. Sadly, only two of those wins came for the Phillies before they gave him away.

#1. Larry Bowa and Ryne Sandberg for Ivan DeJesus and Bill Caudill. It’s worth noting that Sandberg was the throw-in on this deal. The Phils tried to give the Cubs Bowa and Luis Aguayo. The Cubs said no, but they’d take Bowa and Sandberg. The Phils caved. The Cubs got a superstar Hall of Famer. The Phils were stuck with Aguayo, who turned out to be serviceable at best, and DeJesus, who was a good glove, played shortstop for the team for 3 years.

Those are the worst 5 trades the Phillies have ever made, but what about the worst trade the Phillies DIDN’T make? Hard to say, and there are probably plenty of them that never saw the light of day. But we do know about one, thanks to Krukker. He told Sam Donnellon a couple of years ago that the Phils were talking to the Mariners in ’93 about trading for Randy Johnson. But the Phils didn’t want to part with Mike Lieberthal, so the trade never happened.

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