Ryan Howard
For someone such as the caliber of the legendary Ryan Howard, one wouldn’t have expected that a bad contract would materialize for a player with such pedigree. After all, he was one of the key backbones of the Phillies’ resurgence back into prominence during the 2000s.
Howard captured NL MVP honors in 2006, along with finishing in the top five in MVP voting on three other separate occasions. He was also instrumental in helping the Phillies bring home their second-ever World Series title in 2008, as well as keeping them in contention every year during a span of five seasons from 2007 to 2011.
With all the accolades he had accumulated, it seemed like a no-brainer at the time for the Phillies to keep the superstar as long as possible. As a result, Philadelphia locked him in when they agreed to a five-year, $125 million contract extension that would keep him with the Phillies up until the 2017 season.
However, following his typical strong offensive output during the 2011 season, Howard went on the decline for practically the remainder of his big contract. Hampered by Achilles and knee injuries along the way, he batted below .230 and produced less than 80 RBI in four of the five seasons from 2012 to 2016. On top of that, Howard never managed more than 65 runs scored and 25 home runs during that time span, after averaging greater than 80 runs scored and close to 40 home runs per season previously.
As expected, with Howard’s struggles, the Phillies’ playoff hopes also went down the drain. In the end, he didn’t last the entire contract as the Phillies eventually exercised their buyout option during the 2016 offseason to officially release the aging star. Probably not the best way to send off the legend, but the Phillies needed to move on from Howard to get the team back on track.
Scott Kingery
If there was ever the perfect example of when not to reward a player with a large contract before they have actually proven themselves to be worthy of it, Scott Kingery sure comes closest to it. Whether the Phillies were that certain of his potential, or whether they were just out of their minds, they signed Kingery to a six-year, $24 million contract despite having not played a single MLB game in his professional baseball career.
That certainly turned out to be a huge gamble based on potential, a gamble that ended up blowing up in their faces.
Following a decent first couple of seasons in 2018 and 2019, Kingery fell off a cliff in 2020 during the COVID-shortened season in which he batted just .159 with a .511 OPS with just 12 runs scored, five doubles, three triples and six home runs in 36 games played.
Hindered further by injuries and ineffectiveness, Kingery went on to appear in just 16 games with the Phillies over the next two seasons while spending the bulk of his time with the Triple-A affiliate Lehigh Valley IronPigs. He was never able to work his way back up to the big leagues despite showing glimpses of hope along the way. As a result, Kingery was finally dealt to the Los Angeles Angels on Nov. 1, officially ending his tumultuous tenure with Philadelphia.