While the Philadelphia Phillies have fared relatively well over the last several years with their free-agent signings — Bryce Harper, Kyle Schwarber, Zack Wheeler, and J.T. Realmuto, just to name a few — the franchise is littered with terrible decisions over the decades. We take a look at the 10 worst free-agent contracts in Phillies history.
10. Michael Saunders: One year, $9 million
Coming off an All-Star season in 2016 with the Toronto Blue Jays, the Phillies handed Michael Saunders a one-year, $9 million deal going into the 2017 season. He didn’t even last through the summer. He was released at the end of June after slashing just .205/.257/.360 and hitting only six home runs in 61 games.
9. Mike Jackson: One year, $3 million
After saving 40 and 39 games in 1998 and 1999 for the Cleveland Indians, the Phillies gave closer Mike Jackson, who turned 36 prior to the 2000 season, a one-year, $3 million deal. He never threw a pitch as he suffered an elbow injury and missed the entire year.
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8. David Bell: Four years, $17 million
In the same offseason the Phillies signed Jim Thome, they also inked his former Cleveland teammate David Bell to a four-year, $17 million deal. It did not work out, to say the least. The third baseman hit .195 in his first year of the deal and had an OPS+ of just 84 over three seasons in Philadelphia. The Phillies cut their losses and traded Bell to the Milwaukee Brewers at the 2006 trade deadline.
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7. Didi Gregorius: Two years, $20 million
The Phillies retained shortstop Didi Gregorius in free agency after a stellar COVID-shortened season in 2020. Over 60 games, Gregorius slashed .284/.339/.488, hitting 10 home runs, with a 120 OPS+. The Phillies rewarded him with a two-year, $20 million deal. However, his numbers nosedived the next two seasons, and Philadelphia ended up releasing him after he played in 63 games in 2022.
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6. Lance Parrish: Two years, $2 million
Lance Parrish was supposed to be the Phillies’ franchise catcher. After six All-Star seasons with the Detroit Tigers, the Phillies signed Parrish to a two-year, $2 million contract ahead of the 1987 season. It turned out to be a major dud. Over two seasons, Parrish hit .230 with a .689 OPS and 87 OPS+. It was definitely not what the Phillies envisioned at the time.
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5. Jake Arrieta: Three years, $75 million
The 2015 National League Cy Young Award winner signed a three-year, $75 million deal with the Phillies prior to the 2018 season. Philadelphia was hoping Jake Arrieta could help anchor the rotation with ace Aaron Nola. However, it turned out to be a mediocre signing. Not only did Arrieta fail to show his former All-Star form, he would also talk negatively about some of his teammates to the media following games. He had a 4.36 ERA and an ERA+ of 98 over 64 starts with the Phillies.
4. Gregg Jefferies: Four years, $20 million
Coming off back-to-back All-Star seasons with the St. Louis Cardinals, the Phillies shelled out a four-year, $20 million contract to Gregg Jefferies. Philadelphia was hoping he would turn out to be their next superstar — it was anything but. He was hurt frequently during his tenure and only had 37 home runs over three-and-a-half seasons before the Phillies shipped Jefferies to the Anaheim Angels in 1998.
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3. Adam Eaton: Three years, $24 million
The Phillies thought they were bolstering their rotation going into the 2007 season when they gave Adam Eaton a three-year, $24 million contract. However, it was an unmitigated disaster. In his first season, he had a 6.29 ERA. He followed that up in 2008 with a 5.80 ERA in 19 starts before being demoted to Triple-A. The Phillies cut their losses with Eaton ahead of the 2009 season and released him. He will forever be remembered for being booed during the Phillies’ World Series ring ceremony at their 2009 home opener.
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2. Danny Tartabull: One year, $2.3 million
The Philadelphia Phillies thought they were getting a slugger to help anchor their lineup going into the 1997 season when they signed Danny Tartabull to a one-year, $2.3 million contract. Tartabull was coming off a 27-home-run season with the Chicago White Sox. However, this turned into one of the worst signings in Phillies history. He broke his toe in his very first at-bat with the Phillies after fouling off a ball. He would end up playing in just three games for the season.
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1. Taijuan Walker: Four years, $72 million
The No. 1 spot on our list goes to pitcher Taijuan Walker. The Phillies gave Walker a four-year, $72 million contract ahead of the 2023 season. Walker was coming off an All-Star season with the New York Mets. The Phillies thought they were going to get that version who would eat up a lot of innings. Instead, it’s just been a nightmare. He has a 5.27 ERA across two seasons, including a 7.10 ERA in 2024 when he was demoted to the bullpen. Walker has also been left off the postseason roster the last two seasons, causing the Phillies to look for more backend-of-the-rotation help this offseason.