8 worst contracts in Philadelphia Phillies history

The Phillies sure didn’t get the results they were hoping for with these doomed deals.

New York Mets v Philadelphia Phillies
New York Mets v Philadelphia Phillies | Rich Schultz/GettyImages
4 of 5

Jake Arrieta 

When the Phillies signed right-handed pitcher Jake Arrieta to a three-year, $75 million deal during the 2017-18 offseason, they believed that they had found a co-ace to tandem with Aaron Nola to anchor the rotation for years to come. After all, the former NL Cy Young winner had been one of the best pitchers in all of baseball during his previous four and a half seasons with the Chicago Cubs.

Constantly maintaining an ERA close to 3.00 while posting a stellar winning percentage of .635, Arrieta also played a key role in helping the Cubs to their first World Series championship in over 108 years in 2016. The Phillies were looking forward to seeing him bring that success to the club in their own pursuit of the World Series.

However, Arrieta became a shell of his former Cy Young-caliber self after joining the Phillies. In his three seasons in Philadelphia, he compiled a 22-23 record with a 4.36 ERA and 1.39 WHIP, with just 280 strikeouts in 352 2/3 innings of work over 64 starts. More importantly, Arrieta did not help take the Phillies to the next level as they failed to make the postseason in each season during his tenure with the club. He would eventually spend one more year in the majors after leaving Philadelphia and officially retired the following year in 2022.

Didi Gregorius 

Prior to joining the Phillies in 2020, shortstop Didi Gregorius was coming off 20+ home runs and 70+ RBI seasons in three of his previous four years with the New York Yankees. Gregorius was looked upon to help complement the Phillies’ offensive attack with stars J.T. Realmuto, Rhys Hoskins, Andrew McCutchen and Bryce Harper already a major part of the team.

In his first year with Philadelphia, Gregorius put together a solid season in which he batted .284 with an .827 OPS, along with 34 runs scored, 10 home runs and 40 RBI in 60 games played. Appearing to have their answer for the shortstop position, the Phillies re-signed Gregorius to a generous two-year, $28 million contract after the 2020 season.

What the Phillies didn’t expect, though, was the massive regression in his game that quickly followed. In 2021, Gregorius posted a career-low .209 batting average, along with a .639 OPS, 35 runs scored, 16 doubles, 13 home runs and 54 RBI in 103 games played.

In 2022, things fell off a cliff as he suffered a power outage, hitting just .210 with a .567 OPS, 17 runs scored, nine doubles, one home run and 19 RBI over 63 games. Gregorius didn’t even end up lasting the season, as he was eventually released in early August to help make room for up-and-coming rookie Bryson Stott to take his place on the roster.

If things weren’t already bad enough for the Phillies, because $9.5 million of Gregorius’ salary was deferred at the time of his contract, Philadelphia is still paying him to this date and will continue to do so until the end of 2026.

Schedule