PHILADELPHIA, PA - SEPTEMBER 30: Wide receiver Ramses Barden #13 of the New York Giants catches a pass in front of cornerback Nnamdi Asomugha #24 of the Philadelphia Eagles at Lincoln Financial Field on September 30, 2012 in Philadelphia, Pennsylvania.

Eagles free agency is well underway. At least so far, people seem very happy with what Howie Roseman has done. He landed one of the top edge rushers, the best RB in the league, and brought CJ Gardner Johnson back to Philly. Could some of these deals go sideways?

Of course. Big RB contracts are notorious for ending poorly.  But at least on paper, the free agents he brought in were great moves

EAST RUTHERFORD, NEW JERSEY - DECEMBER 11: Saquon Barkley #26 of the New York Giants celebrates after scoring a five yard touchdown against the Green Bay Packers during the second quarter in the game at MetLife Stadium on December 11, 2023 in East Rutherford, New Jersey.
(Photo by Sarah Stier/Getty Images)
(Photo by Sarah Stier/Getty Images)

As Philly sports fans though, we are all too familiar with these moves blowing up in our faces. We have all gotten excited about a move one of our teams made way too soon. Every one of us has a Jersey buried somewhere in our closet of a big-name player who came here and then proceeded to be terrible. I know I have a couple of purchases I deeply regret.

That goes past just free agency and into trades as well. Eagles, Sixers, Phillies, Flyers. All 4 have made regrettable decisions in free agency over the years. Between giving too much money to players past their prime, overpaying for someone coming off one good year, or just overrating a player to begin with because they were desperate.

Check out more about what the Eagles have done in free agency below:

But what are the worst moves our teams have ever made? Which free agents were the biggest busts? What trades were the most regrettable? In honor of free agency kicking off in the NFL, let’s look back at some of the worst acquisitions our teams ever made.

Here are 10 of the worst free agents or trades in Philly sports history:

  • Andrew Bynum

    Saying Andrew Bynum sucked here is inaccurate. He never played to either suck or not suck. Bynum spent one season in Philly. In that year, he bowled more than he played Basketball. The Sixers gave up a haul to acquire him from the Lakers and then paid him $16 million, to never step on the court at The Well Fargo Center.

    There was so much hype around him. He got a huge introduction with fans treating him like a savior. Then we never saw him again. Our biggest memories of his Sixers career are his weird haircuts, his bowling injuries, and the fact he once pulled up to the Sixers Practice Facility dragging a gas station pump hose behind his Ferrari.

  • Nnamdi Asomugha

    I personally was a victim of the hype when they signed Nnamdi Asomugha. In 2011 they signed him to a 5 year, $60 million deal. He was part of a slew of Eagles moves that got that year’s team infamously dubbed “The Dream Team,” by Vince Young. Honestly, there are several players from that free agent class who could make this list. But Nnamdi was the biggest disaster of the bunch. 

    He only lasted for 2 of those 5 seasons before was cut by the team. One of the most hyped signings by the Eagles in my lifetime, and it was an immediate bust. The “Dream Team went 12-20 in those two seasons. LeSean McCoy and Asante Samuel talked about how they realized he was going to be a bust here on the first day of practice. And they were right. All that came of Nnamdi’s time here was bringing an end to the career of the best coach in Eagles history, Andy Reid, and a lot of wasted money on Nnamdi jerseys.

  • Jake Arrieta

    To be fair to Jake, his tenure in Philly was better than the last two guys. But that is about the only good thing we have to say about him. The Phillies signed him to a 3-year, $75 million deal in 2018. His time with the Phillies is not only defined by his poor performance, but by being a bit hard to like off the field too. He was someone who liked to throw blame around, even though he wasn’t performing himself.

    His ERA, while he was here, was 4.36. $25 million a year, to be a below-average starter. He played poorly on the field and was often a jerk off it. All of his talk about accountability, he never took any accountability of his own.

  • Ilya Bryzgalov

    Bryzgalov was an interesting fellow. A terrible goalie while here, but entertaining in other ways. Who can forget his infamous rant about how big the universe is? Or when he quipped that he wasn’t scared of the Penguins and that only bears in the woods scared him. If only his goaltending was as great as his quotes.

    The Flyers invested a ton to bring him in. Not only did they give him a “humongous big” nine-year, $51 million contract, but they traded away Mike Richards and Jeff Carter to fit him in. He only made it two years into that contract here. In 2013 they bought out the final 7-years of his contract. They are still paying it out to this day. 

  • Demarco Murray

    In fairness to Murray, this was not all his fault. Chip Kelly had no clue how to use him. They traded away LeSean McCoy, and signed Murray, with the pretext that he was more of a downhill runner. But then Chip used him as if he were LeSean McCoy. They gave him a 5-year $42 million contract and then refused to use him for what he was known for in Dallas.

    Murray was coming off a 1,800-yard season with the Cowboys. In his one year in Philly, he gained only 702 yards and averaged 3.6 yards per carry. It was a disaster of a signing. Chip Kelly was fired before the end of the year, and in the offseason, the Eagles traded him to the Titans for a swap of 4th-round picks. He went from being the most productive RB in the league to only being worth moving up 13 picks in the 4th round. He did end his time with the Eagles on a high note. Scoring this TD that helped them win a meaningless game after Chip Kelly was fired.

  • Chris Webber

    MIAMI - APRIL 14:  Chris Webber #4 of the Philadelphia 76ers reacts after turning the ball over in the second half against the Miami Heat at American Airlines Arena on April 14, 2006 in Miami, Florida. The Heat defeated the 76ers 104-85.

    Chris Webber is a Hall of Fame Player. Just not with the Sixers. He was brought in to be the Robin to Allen Iverson’s Batman. Unfortunately, he was more like the Jason Todd Robin. He struggled to find his place in the Sixers’ offense the first year, averaging just 15.6 pts per game. To his credit in the first-round matchup vs the Pistons he stepped up with over 20 per game, but that wasn’t enough to help them win.

    He played better the next year, but the Sixers missed the playoffs. Then he was bought out early in his third season here. His tenure in Philly was marred by injuries that seemed to have sapped the quickness that made him a Hall of Famer. Webber became the latest in a string of failed attempts to find AI a co-star.

  • Adam Eaton

    NEW YORK - APRIL 11: Adam Eaton #23 of the Philadelphia Phillies throws a pitch during the MLB game against the New York Mets at Shea Stadium on April 11, 2007 in the Flushing neighborhood of the Queens borough of New York City.

    Adam Eaton was a bad move. That was immediately apparent. The Phillies brought him in for the 2007 season on a 3-year $24 million deal. He was among the worst pitchers in Baseball that year with a 6.29 ERA. But did he bounce back in 2008? Nope. He followed that up with a 5.80 ERA across 19 starts. He was so bad they replaced him with Joe Blanton. He was sent to the minors and never pitched for the Phillies again.

    In terms of money wasted, he is not the worst. But in terms of sheer incompetence, he was awful. He was a mediocre pitcher to start, got paid too much, and then was even worse in Philadelphia. And this guy, who was so bad he was kicked out of the rotation, had the gall to claim he helped the team win a World Series.

     “A lot of things went wrong, but a lot of things that went right, too. I helped them get to the playoffs two years in a row, and obviously we won the World Series last year. That’s a big thrill of mine, but obviously I still want to compete in that World Series atmosphere. That’s what I aim to do.”

  • Byron Maxwell

    The other famous bust of a CB signing for the Eagles. At least Nnamdi was great before he came here though. Maxwell was the third wheel in a stacked Seahawks secondary, and everyone at the time was questioning if he would struggle if asked to be the CB1. Turns out, he would. His one year in Philly was a disaster. But that’s not surprising when you pay a guy with 17 starts that much money.

    The Eagles gave him a 6-year, $63 million deal. he only lasted one year. His first year sucked, and then the Eagles somehow managed to not just dump both his and Kiko Alonso’s contract, but move into the draft while doing so. This led to them getting Carson Wentz. And while Wentz’s tenure was a disaster by the end, they don’t win a Super Bowl without him.

    So in the end the Byron Maxwell contract may have paid out. He still sucked though. Maxwell took it personally and said he wanted to prove the Eagles wrong. He did not. In fact, they won the Super Bowl shortly after trading him, and Maxwell’s career keep trending down.

  • Matt Geiger

    6 Jun 2001: Matt Geiger #52, left, and Allen Iverson #3 of the Philadelphia 76ers in action in Game 1 of the NBA Finals against the Los Angeles Lakers at Staples Center in Los Angeles, California. DIGITAL IMAGE

    I still don’t understand why the Sixers paid Geiger what they did. They gave him a 6-year $51 million deal. Why? I have no clue. He was a backup quality center averaging 8.9 points and 5.7 rebounds in 21.9 minutes per game. What about that screamed payday? Predictably, the contract went poorly. He barely played. Injuries plagued his time in Philly and retired by 2002. In 2001 he made about $12k per minute.

    The one good thing he did for the Sixers was preventing them from trading Allen Iverson. AI was almost sent to Detroit in 2000. But Geiger refused to waive his trade kicker, killing the deal. It was the one good thing Geiger did in a Sixer’s uniform. preventing what could have gone down as an All-Time bad trade.


  • Stacy Andrews

    PHILADELPHIA, PA - APRIL 29: In this 2010 photo provided by the NFL, Stacy Andrews of the Philadelphia Eagles poses for an NFL headshot on Thursday, April 29, 2010 in Philadelphia, Pennsylvania.

    After Stacy Andrews, older brother of Shawn Andrews, had a few good seasons with the Bengals, the Eagles decided to make a splash. They brought him in to unite him with his brother with a 6-year, $38.9 million contract. He lasted only one. One year into the plan to have the Andrews brothers on the line together, both were gone. Shawn Andrews was released after injuries kept him off the field. Meanwhile, Stacy also dealt with injuries, and frankly looked awful when he did play. He was benched and eventually traded.

    Stacy started only two games for the Eagles. The Eagles unloaded him to the Seahawks for a 7th-round pick in the off-season. He was out of the NFL two years later after spending time in Seattle and with the Giants.

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