8 worst contracts in Philadelphia Phillies history

With free agency season officially underway, the Philadelphia Phillies are looking for impactful players on the market who can help the team for the upcoming season and possibly beyond. One of the keys to long-term success is being able to find candidates who can, at minimum, provide the value of the respective contract size that they end up signing. 

In recent times, the Phillies have done exactly that with the big-time signings of perennial Cy Young contender ace Zack Wheeler and superstar Bryce Harper. To date, they have certainly delivered what had been expected of them and perhaps even more at times. However, for every successful signing, there are bound to be some contract mistakes that the Phillies probably wished never took place.

Here, we will take a look at eight of the worst contract signings in Phillies history and how they turned out miserably, despite showing some potential or promise.

8 worst contracts in Philadelphia Phillies history

Lenny Dykstra

Prior to the Jimmy Rollins era with respect to stud leadoff hitters in franchise history, the Phillies had another bonafide one in the early 1990s in Lenny Dykstra. After all, Dykstra was a former three-time All-Star, one-time Silver Slugger and NL MVP finalist.

He was one of the big reasons behind the Phillies’ surprising drive to the World Series in 1993 before they just fell short to the Toronto Blue Jays in six games. Nevertheless, 1993 was still a season worth remembering for Dykstra as he led the NL in runs scored (143), hits (194) and walks (129), along with posting career-highs in batting average (.305), OPS (.902), doubles (44), home runs (19), RBI (66) and stolen bases (37).

The Phillies quickly secured his services by reaching an agreement on a four-year, $24.9 million contract extension, making him the highest-paid leadoff hitter in baseball history at the time. His $6.2 million AAV was also the seventh-highest annual salary in MLB as of that moment as well.

However, Dykstra never got close to reproducing his MVP-like numbers from that 1993 season after signing the extension. Following a decent 1994 season in which he hit .273 with an .839 OPS with 68 runs scored, 26 doubles, five home runs, 24 RBI and 15 stolen bases in 84 games, injury woes plagued the star outfielder for the remainder of his career.

He would be limited to just 102 games between 1995 and 1996, amassing 58 runs scored, 21 doubles, five home runs, 31 RBI and 13 stolen bases over that stretch. More significantly, he was forced to miss the 1997 season completely after undergoing surgery to treat a serious nerve condition known as spinal stenosis.

Dykstra attempted a return in 1998 but ultimately called it a career when he failed to make any progress. There’s no doubt he would have had a bigger impact on the Phillies without his ailments, but his disappointing output as a result of something he essentially had no control over left a lot to be desired.

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.

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.

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.