Philadelphia Phillies: The 10 worst trades in franchise history

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Phillies Trade Ryne Sandberg

The top two worst trades on our list are pretty interchangeable and we won’t fault you if you flip them because it is legitimately pretty close. In 1982, Larry Bowa (a familiar face) was getting older and when the two sides couldn’t agree on a path forward, the Cubs swooped in with a trade proposal that had them send Ivan DeJesus, who could replace Bowa at short for Philly, for Bowa and some young infielder named Ryne Sandberg.

Yeah, THAT Ryne Sandberg. Philly didn’t think much of Sandberg back in those days, but the Cubs saw potential in him and they were very, very correct. DeJesus was not the long-term answer at short that Philly was hoping for as he played just three meh to bad seasons while the Cubs got a future MVP, multi-time All-Star, multi-time Gold Glover, and, of course, Hall of Famer. Again, if you have this as the worst trade in franchise history, we won’t argue.

Phillies Trade Fergie Jenkins

At number one on our list is a classic example of a failure in player evaluation of epic proportions. Fergie Jenkins was a seldom used bullpen arm in Philadelphia and was included in a package sent along with John Hernstein and Adolfo Phillips to the Cubs for Larry Jackson and Bob Buhl. No, it didn’t escape our notice that the Cubs are responsible for the three worst trades in franchise history and yes, it definitely tilted us.

Once the Cubs got ahold of Jenkins, they would convert him into a starter and he would put together a seven year run in the late 1960’s and early 1970’s where he would win 141 games and post a 3.11 ERA and 44.9 rWAR while winning the Cy Young in 1971. He would pitch until 1983 where he returned to play the final two years of his career in Chicago. It took longer than it should have, but Jenkins was eventually inducted into the Hall of Fame in 1991 having pitched 4500.2 in the big leagues as one of the best to ever do it.

As for Philly’s return in the deal, Jackson put together a few decent seasons in Philadelphia while Buhl didn’t do much of anything before retiring a couple of years later.

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