Some of the Worst Trades in Phillies History

Grover Cleveland Alexander. Photo by Charles M. Conlon. (Public Domain)

As a franchise that’s only won two World Series titles in its 130-plus-year history, the Philadelphia Phillies have made a boatload of bad decisions. (And some good ones, too, which is fodder for future posts). Here are four of the most egregious player transactions – but there are many others that could’ve made the list:

  1. In 1982, infield prospect Ryne Sandberg and veteran shortstop Larry Bowa are dealt to the Chicago Cubs for shortstop Ivan DeJesus. Bowa was at the end of his career, and DeJesus was an OK player, so that part of the trade was fine. It was the Sandberg part that was the problem. Ryno turned into a Hall of Fame second baseman for the North Siders, winning the National League MVP in 1984 and playing in 10 All-Star Games. At the time of his retirement, Sandberg had 282 home runs, which was the most for a second sacker until that career total was surpassed by Jeff Kent. Oh, and he won nine Gold Gloves as well.
  2. Until I was a young adult and leafed through my father’s 1965 Phils yearbook, I didn’t even know Ferguson Jenkins had been signed by Philadelphia. But there he was, as a rookie. Jenkins barely got a cup of coffee with the Phillies before they shipped him to the Cubs, along with John Hernstein and Adolfo Phillips, for pitchers Bob Buhl and Larry Jackson. Jenkins retired with 284 victories, including seven 20-win seasons and a Cy Young Award. His Hall of Fame page notes that he was the first pitcher to retire with 3,000 strikeouts and fewer than 1,000 walks. Manager Leo Durocher said of Jenkins: “He was one of the best pitchers in baseball, ever.”
  3. Speaking of one of the best pitchers in baseball, Hall of Famer Grover Cleveland Alexander actually got to pitch for the Phils – for a while, at least – prior to being traded in 1917 to the Cubs with some other guys in a package that included a player named Pickles Dillhoefer. (They don’t make baseball nicknames like they used to.) Alexander won 190 games for the Phillies and led them to the 1915 World Series, which they lost to Babe Ruth and the Boston Red Sox. He was 30 years old at the time; he ended up winning 183 more games and pitching into his 40s.
  4. This deal may have not even made the top 10 on others’ lists, but I wanted something more recent. In late 2006, Phils’ GM Pat Gillick sent pitching prospects Gavin Floyd and Gio Gonzalez to the Chicago White Sox for fellow starter Freddy Garcia. I love Gillick, because he was instrumental in bringing a World Series championship to Philly. But even the best general managers make mistakes, and this one was a doozy. Though he won 17 games the year before and had a good track record, Garcia was horrible in his one season with the Phillies, while Floyd was solid for several seasons and Gonzalez has been even more productive. Still active, Gonzalez owns 130 major league victories, a 21-win season with the Washington Nationals in 2012, and two All-Star Game appearances.

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