Gregg Jefferies
After two All-Star seasons with the St. Louis Cardinals in which he hit above .325 with close to a .900 OPS between 1993 and 1994, Gregg Jefferies earned himself a big paycheque with the Phillies during the 1994-95 offseason as he was signed to a four-year deal worth $20 million.
With hopes that they could ride his bat back into contention for the near future, Jefferies was never able to reproduce the breakout season he had in 1993 when he posted an impressive .342 average, .894 OPS, with 89 runs scored, 16 home runs, 83 RBI, 46 stolen bases, 62 walks and just 32 strikeouts in 142 games played.
Instead, in his four seasons with the Phillies, Jefferies averaged just 65 runs scored, nine home runs, 51 RBI and 13 stolen bases each year while batting .287 with a .751 OPS. He hit for the cycle in 1995. More importantly, the Phillies failed to become playoff contenders once again as they finished below .500 in each of those four years and were ultimately shut out from the postseason.
Philadelphia finally ended Jefferies' disappointing tenure with the club by trading him to the Anaheim Angels in 1998 for a player to be named later. That player turned out to be Doug Nickle, who quickly became a player of insignificance, leaving the Phillies with nothing to show for their big investment.
Adam Eaton
Despite posting pedestrian numbers for the bulk of his MLB career, Adam Eaton somehow caught the eye of the Phillies when they signed him to a three-year contract worth $24 million during the 2006-07 offseason to help bolster their rotation anchored by Cole Hamels.
Perhaps it was due to his ability to eat innings, as he had averaged close to six innings per start for his career. But if the Phillies were looking for miracles to happen and that Eaton would all of a sudden take his game drastically to another level, it certainly didn’t end up materializing as the right-hander struggled for the bulk of his tenure with the club.
In his first two seasons with Philadelphia, Eaton compiled a 14-18 record with an abysmal 6.10 ERA and 1.63 WHIP, giving up 182 earned runs with 115 walks and 154 strikeouts in 268 2/3 innings pitched over 51 appearances that included 49 starts. You definitely knew that things weren’t going well at all when he was optioned to the minors in late July of 2008 and was consequently left off the postseason roster during the Phillies run to the World Series championship.
Without taking any more chances with their mistake that blew up in their faces, the Phillies subsequently released the right-handed veteran pitcher ahead of the 2009 MLB season, being forced to eat the remainder of his contract.