Some contracts turn bad because of injuries, others through age or poor performance. The worst were bad ideas the minute they were signed. Signing a bad contract doesn’t make the player a bad person, but as soon as the performance stops matching the dollars we sour on once great players. It’s just how it goes. Let’s go back over the last 20 years and look at some of the worst contracts in Philly sports in chronological order
Chris Pronger Extension – July 8, 2009
On June 26th, 2009 the Flyers traded 2 1st round picks for Chris Pronger then immediately gave him a 7/$34.5m extension. Pronger had been an elite defenseman for a very long time1…perhaps too long. Pronger was almost 35 when the deal was made. The Flyers knew this and were investigated for salary cap manipulation. Pronger had one incredible season for the Flyers that resulted in one of the best non-Cup winning runs a team could have. The next season was marred by injuries and eventually concussions that ended his career. The Flyers were still on the hook for around 5/$25m to which he would only play 13 games.2 This was somewhat alleviated by Long Term Injured Reserve, but still an impediment.
Ryan Howard Extension – April 26, 2010
So often in sports we get mad at ownership for not taking care of our favorite players. They move on and we lament their foreign jerseys forever. Ryan Howard is the opposite. Only 1 year after signing a fair 3/$54m extension coming off the World Series win, the Phillies doubled down on Howard, giving him a 5/$125m extension. The problem was that his numbers had already begun to plummet because he always pulled the ball into the shift and could not hit lefties. Instead of his contract running out after 2011 when his Achillies tendon exploded, it went on through 2016. He piled up -5 WAR in that time. Even though there is no salary cap in MLB, this one handicapped the Phillies for years. I love Ryan Howard, but this was just completely unnecessary.
Ilya Bryzgalov Extension(-ish) – June 23, 2011
Sweet merciful crap, despite it being hockey this might be the most legendary bad contract out there. The Flyers traded for the Bryz then signed him to a massive 9/$51m contract the same day that they traded away fan favorites Mike Richards and Jeff Carter. Bryz was better than you would think on the ice at first, but seemed like a lunatic off of it, alienated his teammates, and ended so bad that the team had to use a compliance buyout to get off his contract. THEY ARE STILL PAYING HIM!!!
Nnamdi Asomugha Free Agent – July 29, 2011
The lead member of the ill-fated Dream Team Eagles signed for 5/$60m…and it was awesome! Nnamdi was the undisputed best CB in football and fresh off 1st Team All Pro seasons in 2008 and 2010 (2nd team in 2009). Other than him being 30, what wasn’t there to be excited about? I still have no idea what happened, but he went from the best to one of the worst seemingly overnight, was a weirdo with his teammates, and was released after 2 bad seasons. He would only play 3 more games in the NFL. He came to be the poster child for all that went wrong with the Eagles in the post McNabb era.
Demetress Bell Free Agent – April 4, 2012
The entire Demetress Bell story is strange starting from the day he was born.3 Bell was a 7th round pick by Buffalo who didn’t play at all his first year, then was hurt in much of his next 3 years with the Bills playing only 30 games in 4 seasons. The Eagles then decided to give him 5/$35m to replace Jason Peters after his Achillies tendon injury. He would get in 9 games (5 starts) in his only season with Philly, was released, and never played again.
Byron Maxwell Free Agent – March 10, 2015
The Eagles and free agent CBs do not have the best track record. After learning nothing from the Nnamdi mistake, the Eagles gave a 6/$63m contract to Maxwell who had only started in Seattle for one season. They Eagles (and Chip Kelly) paid him at the top of the market anyway. Upon Chip’s termination, Howie Roseman promptly traded Maxwell (along with Kiko Alonso) to the Miami Dolphins to move up from #13 to #8 in the draft.4 Despite signing the deal at age 27, Maxwell was out of the league before he turned 30.
DeMarco Murray Free Agent – March 12, 2015
Just a hell of a week for lead decision maker Chip Kelly. Two days earlier, Chip traded LeSean McCoy to the Buffalo Bills in a move that could have been considered smart under the theory that any running back could probably succeed in a Chip offense. Of course, this theory was immediately detonated when the Eagles gave Murray a 5/$40m deal. Murray led the NFL in damn near every RB category the previous year in Dallas, but also ran himself into the ground with 450 touches. His production completely tanked in Philly and he was traded after 1 season. Not unlike Maxwell above, Murray was out of the league before turning 30.
Jake Arrieta Free Agent – March 11, 2018
Arrieta had an unbelievable 2015 season, winning the Cy Young with a 1.77 ERA over 229 innings. Then he fell off. By the winter of 2017-18, no one thought he was getting back to that level again. The Cubs were done with him and he did not seem to have a good market. That didn’t stop the Phillies from giving him a 3/$75m hybrid contract that made no sense. To his credit, he pitched not terribly that first year but it got worse from there. Never for a second was he worth $25m per season and everyone but the Phillies knew it.
Carson Wentz Extension – June 6, 2019
When the Eagles signed Wentz to his 4/$128m extension, it seemed like a good idea. Starting QBs in the NFL get paid and the Eagles got ahead of other extensions. The previous year, Aaron Rodgers was the high watermark at $33.5m per season with Matt Ryan second at $30m. Wentz went first, then Russell Wilson, Ben Roethlisberger, and Jared Goff passed him. Of course, you still need the QB to perform to get value on the contract. Wentz didn’t. He immediately felt threated when the team drafted Jalen Hurts and fell off a cliff. The good news is that despite taking on a $34m dead cap hit by trading him, the Eagles gained the picks that would lead to Cooper DeJean, AJ Brown, and Jalen Carter.
Tobias Harris Extension – July 10, 2019
I don’t blame Tobias Harris for signing his 5/$180m extension with the Sixers, I blame the Sixers for offering it. Sports teams regardless of league get in trouble when they overpay mediocre players. That’s exactly what Harris always was. Even if you took him on his best day, he was never a star. The Sixers paid him like one anyway. For other reasons (see below), Jimmy Butler was not given the same contract and the Sixers were hamstrung for 5 years because of it. Harris infamously ended his Sixers career with a 0-point playoff elimination performance. The funny (like crying-my-eyes-out-and-want-to-hurt-myself funny) part is that as soon as the Harris contract was off the books, we immediately signed Paul George to be the same thing. 9 years of wasting max cap space. WTF!
Al Horford Free Agent – July 10, 2019
What a dark day in Sixers history. The idea made sense on paper. Signing Al Horford to a 4/$109m deal got the Embiid-kryptonite away from the arch enemy Celtics while also giving the Sixers a power forward/backup center they desperately needed. Of course, none of this went to plan. Not only did Horford look like a Boston sleeper agent sent to destroy us, but we ended up dealing Jimmy Butler to accommodate Horford’s contract (kind of). The Sixers had to trade a 1st round pick just get rid of him (will come due this season) and he ended up going back to the Celtics on the cheap to win a title. No signing on this list makes me madder than this one. What an absolute disaster.
Ben Simmons Extension – July 16th, 2019
It made total sense when we gave him a 5/$177m max extension the first minute he was eligible. Simmons was a former #1 pick who seemed like aside from shooting there was nothing he couldn’t do on a basketball court. Eventually, there was almost nothing he could do on a basketball court including dunk on the foot shorter Trae Young in the playoffs. This signaled the end of Simmons in Philly, he pouted and demanded a trade, eventually getting fined $18m for not playing. The saga finally ended with his trade to the Nets for James Harden.
Sean Couturier Extension – August 26, 2021
Couts was 28 and 1 year removed from winning the Selke trophy when his 8/$62m contract was signed. Unfortunately, his deterioration had already begun. Despite a great Covid-shortened season, Couturier was riddled with injuries when he signed the deal. The next season he needed back surgery and played only 29 games. The injury would force him to miss the entire next season as well. He has since come back to play reasonably injury free, but he is no longer the two-way center he was when he signed his big extension. This was probably the most unfortunate addition to the list all things considered, just pure bad injury luck.
Nick Castellanos Free Agent – March 22, 2022
When we signed Castellanos for 5/$100m, it was awesome. Fresh off the work stoppage, the Phillies gave us something to be VERY excited about. Unfortunately, it was a bad fit. Casty is a terrible fielder and was miscast in right field when he had nowhere else to go. His bat would have to make up for it, and it simply never did from the start. He is a high strikeout, low walk, decreasingly powerful hitter who is has been engaged in a pissing contest with his manager for a year now. I love the guy, but outside of two playoff series, he has been a total bust. $20m per season when he signed was solid, but it’s the years that were a killer here.
Taijuan Walker Free Agent – December 16, 2022
Three years into his 4/$72m contract, Walker has had two fine years and one dreadful one. The deal itself isn’t the worst thing in the world anymore, but it’s been crippling nonetheless. When the deal was signed, Walker simply got too much. As a 4th starter, both 4 years and $18m per season are too much, but to give him both was just plain irresponsible. Every year it seems like the Phillies are one player short and this $18m would make all the difference.
James Bradberry Extension – March 14, 2023
His original 1/$7.25m contract with the Eagles is one of the best ever considering his 2nd team All Pro selection. Unfortunately, they ran it back. Bradberry signed a 3/$38m deal at 30 years old that aged like milk. Bradberry went from allowing a 51 QB rating in coverage to a 114 rating (and 11 TDs) year over year, and didn’t dress once in the Super Bowl year. Just a worthless extension.
Aaron Nola Extension5 – November 19, 2023
Nola followed up one of the biggest bargain extensions with one of the worst (so far). After an up and down regular season, Nola came alive down the stretch and road that into a great post season. The Phillies rewarded him with an enormous 7/$172m extension. He was better in 2024, but then fell off a cliff last year with the Phillies still owing around 5/$125m, which just happens to be right around what Ranger Suarez just signed for in Boston. Many Phillies fans felt the Nola-coaster was too wild to keep riding that winter, but the Phillies gave him the bag anyway. Now instead of Suarez returning, we have to hope Nola can be adequate enough to simply keep in the rotation.
Paul George Free Agent – July 6, 2024
It’s revisionist history to say we should have been worried when no one else was offering George the 4/$211.5m contract he eventually signed with the Sixers. Only the Clippers had the ability to offer that amount and they didn’t. HOWEVER, we should have been more worried about the league as a whole realizing that 3 max contracts are a poor way of team building these days and have largely moved away from the model. Instead, we went for it on a 34 year old who only played more than 56 games once in the last 5 seasons. Predictably, he was a walking wreck in his 1st Philly season then suspended 25 games for PED use in season 2. YIKES. At least there are only 2 more years left on the deal. DOUBLE YIKES!
Joel Embiid Extension – September 20, 2024
Embiid has been looking good until he missed the last two games (just knee related maintenance, nothing to worry about… EYES BULGE CARTOONISHLY), but none of us realistically think he has turned an injury corner. He is always just one bad step away from being over. The worst part was that this was not news when he signed his 3/$188.25m extension. The even worster part? That extension does not even kick in until NEXT YEAR!!! They just didn’t need to do the deal and now it hangs over the team like a sword of Damocles. Realistically, the team can’t trade him and can’t depend on him. I love Joel but his situation is debilitating for all involved.
All contract info courtesy of Spotrac. All statistical info courtesy of Sports-Reference and all of their affiliates
- That’s probably underselling it considering he was voted one of the 100 greatest players of all time. ↩︎
- This might not seem like much, but remember that the NHL salary cap was only between $60m and $70m during this time. That’s the equivalent to a $15m salary in the NBA or a $23m salary in the NFL today. ↩︎
- Karl Malone is a shithead ↩︎
- Why the hell did Miami make this trade? ↩︎
- Technically not an extension but it gets confusing if I put it as a free agent deal ↩︎
Philly Front Office 
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