Over the last decade, the Phillies haven’t been shy when it comes to splashing some cash in the open market. Beginning with the signing of Cliff Lee in 2011 to bring him back to Philly, and concluding with the $330 million dollar contract awarded to Bryce Harper last offseason, the Phillies front office has long looked to free agents to help bolster their roster.
While many will argue the Lee deal was one of the best signings in franchise history, and the Harper mega-contract appears to be working out great thus far, the Phillies haven’t always been so fortunate. Plagued by years of mediocrity for a majority of the 2010s, the Phillies repeatedly saw their chances at success be tied up in bad free agency contracts.
Whether it’s monumental underachievement, massive overpays, or preferably a combination of both, the Phillies have had their fair share of terrible free agents over the last ten years.
Honorable Mentions: John Lanaan, Laynce Nix, David Robertson
#5. Jonathan Papelbon
Signing with the Phillies prior to the 2012 season, former Red Sox closer Jonathan Papelbon was the team’s last grasp at staying in contention. Handing out a monumental contract worth upwards of $60 million dollars (once the vesting option year was factored in), Papelbon’s large salary would do more harm than good.
While the Phillie faithful would ultimately grow to hate Papelbon for his general antics and apparent hatred for Philadelphia, Papelbon was overall effective at his job. Across three and a half seasons Papelbon would post a 2.31 ERA and 123 total saves. To this day, he is still the franchise’s all-time leader in saves.
Papelbon lands on this list less so for how he performed, and more so for how crippling his contract turned out to be. In an era in which the Phillies really should have started to focus on adding younger talent to re-tool the roster, they were stuck paying an aging closer 12+ million a year.
Throw on the fact that Papelbon ultimately had to be traded away after attempting to fight a sideline reporter (Howard Eskin) and making a crued gesture towards the fans, and it’s clear why his name still elicits disgust amongst Phillies fans.