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
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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.

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