Philadelphia Phillies won 3 teams’ all-time worst trades

The Philadelphia Phillies won the worst Blue Jays trade when they landed workhorse and future Hall of Famer Roy Halladay.

Young Phillies fans will appreciate this one. After falling to the New York Yankees in the 2009 World Series, the Phillies were hoping to make a splash and build an even better rotation. Although it meant parting ways with Cliff Lee (although it shouldn’t have had to come to that), the team was able to pick up Roy Halladay in the all-time worst trade made by the Toronto Blue Jays.

Halladay may have been the last of his kind. Completing games was a huge part of what made him so unique. He led the league in this statistic seven times and ended four seasons with more innings than anyone else in his league. His lifetime 203-105 record and 3.38 ERA combined with his two Cy Youngs and plenty of high finishes in other seasons helped make him a star in Toronto.

When he was traded to the Phillies, the price wasn’t nearly as high as anyone may have suspected in retrospect. Three players, Travis d’Arnaud, Michael Taylor, and Kyle Drabek went to Toronto in the deal. Each was a noted Phillies prospect at the time. None would have significant careers with the Blue Jays, d’Arnaud getting traded to the New York Mets a few years later and Taylor going to the Oakland Athletics that same day. Only Drabek actually pitched for the Blue Jays. He’d go 8-15 with a 5.27 ERA.

The Phillies, by some magic, pulled off the best heist any club has versus the Blue Jays. Halladay won a Cy Young in his first season with Philadelphia. As short as his time was with the ball club, he’ll always be one of the organization’s most beloved pitchers.