
The Philadelphia Phillies are far from perfect when it comes to trades. If the name Ivan de Jesus doesn’t scare you, ask someone a little bit older.
Over at the dot com, I wrote up an article on the worst trades every MLB team has ever made. It was an interesting experiment. Some teams I knew about without doing any research. Others, while the trade was bad, didn’t make a deal that ruined their franchise entirely.
One thing I did notice was how many Phillies trades were a part of this exploration. The Phillies were fortunate enough to be on the winning side of three trades I deemed to be the worst a franchise has made. Twice it brought them a Hall of Fame pitcher. The other time, an outfielder with a pedigree for getting to Cooperstown as well. Any guesses?
The Philadelphia Phillies won the worst Cardinals trade when they picked up one of the best southpaws in the game’s history, Steve Carlton.
The worst trade in St. Louis Cardinals’ history is possibly the best the other way around. It’s hard to imagine Steve Carlton wearing any other uniform. Amazingly, he was with the Cardinals for parts of seven seasons before even joining the Phillies.
Coming off of a 20-9 season with a 3.56 ERA, Carlton was sent to Philadelphia in a straight-up one-for-one swap. Rick Wise was the pitcher headed to St. Louis.
Wise was actually a little younger than Lefty at the time of the deal and coming off of a successful year of his own. Wise was 17-14 with a 2.88 ERA during the 1971 season, his last with the Phillies. He’d spend two seasons with the Cardinals before getting shipped up to the Boston Red Sox. He was good in St. Louis, going 32-28 with a 3.24 ERA.
But that doesn’t compare to what Carlton accomplished in Philadelphia.
Carlton turned it up a notch in 1972, going 27-10 with a 1.97 ERA. He won his first Cy Young and was on track to helping the franchise turn things around. During his 15 years with the Phillies, Carlton would go 241-161 with a 3.09 ERA. This is the kind of performance you would expect an elite player to have over the course of an entire career. This was just what he did with the Phillies.
The Cardinals could have had one of baseball’s greatest southpaws of all-time. Instead, he ended up with our beloved Phillies.

The Philadelphia Phillies won the worst Rays trade when they landed a young kid named Bobby Abreu.
The Tampa Bay Rays—or Devil Rays as they were originally known—haven’t been around long enough to amass too many horrific trades. They’re actually known today as savvy dealers although this wasn’t always the case.
A young outfielder named Bobby Abreu was taken by the Rays (let’s drop the Devil for the sake of the children because they don’t know any better) and then traded that same night to the Phillies for shortstop Kevin Stocker.
Stocker was an okay shortstop for Philadelphia, hitting .262/.347/.350 in his five seasons with them. He was most known for coming up in the middle of the 1993 season and hitting incredibly well for them.
With the Rays, Stocker batted .250/.329/.347 in two and a half years. Meanwhile, Abreu regularly hit over .300, had only one Phillies season with an OBP under .400, and was one of the league’s best at stacking up metrics we wouldn’t appreciate until about a decade or two later.
Abreu’s Phillies totals include a .303/.416/.513 slash line, 348 doubles, 195 home runs, and 254 stolen bases. Although his numbers may not have measured up to some of his peers of the day, this was an absolute steal for the Phillies and a dud of a deal for the other organization involved.

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.

