Money Well Torched: The Hall of Shame for the Worst Contract Extensions in Recent Sports History
There is a special kind of pain reserved for sports fans whose team just handed a bloated, franchise-strangling contract to a player who is — and we cannot stress this enough — clearly not worth it. It's not the sharp pain of a tough loss. It's the slow, grinding, multi-year agony of watching your team's salary cap get eaten alive by a guy who peaked three seasons ago and is now collecting his check like he's got tenure at a state university.
We've compiled the most egregious recent offenders. Pour one out for the GMs who signed these deals. Actually, don't. They made millions making these decisions. Pour one out for the fans.
5. Zach Wilson's Continued Existence on an NFL Roster (Honorable Mention)
Okay, technically this isn't a contract extension in the traditional sense, but the New York Jets' prolonged commitment to Zach Wilson as their quarterback solution deserves some recognition in any conversation about organizational decision-making disasters. The Jets drafted him second overall, watched him struggle in ways that were genuinely difficult to watch, and kept running him back out there with the energy of someone who paid full price for a concert ticket and is determined to enjoy themselves regardless of what's happening on stage.
The real damage here wasn't financial ruin — it was opportunity cost. Every week the Jets committed to Wilson was a week they weren't meaningfully developing an alternative. It's the contract extension that never technically happened but absolutely should never have been implied.
4. The Albert Pujols Situation (MLB — Los Angeles Angels)
This one's older than our five-year window but its legacy continues to define how teams think about aging sluggers, so we're including it as a cautionary tale that keeps on cautioning. The Angels handed Pujols a 10-year, $240 million deal back in 2012, and what they got in return was a decade-long lesson in how dramatically and rapidly a first-ballot Hall of Famer can decline.
To be fair to Pujols, he was still an excellent player when the deal was signed. But the Angels weren't paying for the player he was — they were paying for the player he'd been, and they were committing to that price tag for ten years. The ghost of that contract haunted Anaheim's roster construction for the better part of a decade, limiting their ability to add talent around Mike Trout — the actual best player on earth — and turning one of baseball's most gifted players into a guy who never sniffed a World Series.
What should they have done differently? Shorter term. Significantly shorter term. An aging power hitter with a degenerating hip does not need a decade of financial security from your organization. That's what the Hall of Fame ceremony is for.
3. Simone Fontecchio Aside — The Ben Simmons Extension (NBA — Philadelphia 76ers)
In October 2019, the Philadelphia 76ers handed Ben Simmons a five-year, $177 million max extension. At the time, the argument was defensible — Simmons was a three-time All-Star, an elite defender, and a genuinely unique offensive weapon. The argument did not age well.
What the 76ers were paying for was a player who could not, would not, and apparently had deeply complicated feelings about shooting a basketball. In the modern NBA, where spacing and three-point shooting are essentially oxygen, committing max money to a player who treats the three-point line like a restraining order is an organizational philosophy problem dressed up as a personnel decision.
The contract became fully toxic during the 2021 playoffs when Simmons' shooting anxieties became impossible to ignore, culminating in a fourth-quarter free throw situation against the Atlanta Hawks that Sixers fans will be describing to their grandchildren. The subsequent trade demand, the holdout, the mental health disclosures, the eventual trade to Brooklyn — all of it was downstream of a front office that paid max money for a player whose limitations were always visible if you were willing to look.
Philly could have structured an incentive-heavy deal. They could have negotiated a shorter term with player and team options. They could have used that cap flexibility to build more shooting around Joel Embiid. Instead, they torched $177 million and got a very expensive blockade.
2. Deshaun Watson's Fully Guaranteed Deal (NFL — Cleveland Browns)
In March 2022, the Cleveland Browns signed Deshaun Watson to a five-year, $230 million contract that was — and this is the part that still causes audible gasps at finance conferences — fully guaranteed. Every single dollar. Guaranteed. Before Watson had thrown a single pass for Cleveland. Before the NFL had completed its investigation into the civil lawsuits filed against him.
The Browns front office essentially looked at the landscape of uncertainty surrounding their new quarterback and decided the appropriate response was to remove all financial leverage from their own hands. Watson then received an 11-game suspension, returned to play, and proceeded to be... fine. Not $230 million fine. Not 'we restructured our entire franchise around this guy' fine. Just fine.
The fully guaranteed structure set a precedent that terrified other NFL owners and gave quarterbacks across the league ammunition in their own negotiations. Cleveland's reward for this innovation was a quarterback who, through two seasons, has shown flashes of competence interrupted by stretches that make you wonder whether the front office has ever watched football before.
What should they have done? Literally anything else. Kept Baker Mayfield. Drafted a quarterback. Hired a skywriter to spell out 'we have no idea what we're doing' over FirstEnergy Stadium. All would have been preferable outcomes.
1. Russell Wilson's Contract Extension (NFL — Denver Broncos)
And here it is. The crown jewel. The Mount Rushmore of 'what were you thinking.'
In September 2022, the Denver Broncos extended Russell Wilson — who they'd already traded significant draft capital to acquire — through 2028, adding four years and $161 million to a deal that was already making the franchise's accountants nervous. The total value ballooned to $245 million. The Broncos were betting their entire organizational future on a quarterback who was, at that precise moment, beginning to show everyone that his Seattle success might have had something to do with Pete Carroll and a historically dominant defense.
What followed was one of the most comprehensive on-field failures in recent NFL memory. Wilson looked lost. The offense was historically bad. Head coach Nathaniel Hackett was fired after 15 games. And through it all, the Broncos were contractually obligated to keep paying a man who had essentially forgotten how to play quarterback.
Denver eventually traded Wilson to Pittsburgh — where he had another year of being visibly not good — but the dead cap money and draft capital lost in the acquisition will burden the Broncos' roster construction for years. The front office that made this decision, led by George Paton, did so with the energy of someone who had just discovered what a quarterback was and wanted to own the nicest one available regardless of price.
The lesson, as always: never pay for what a player used to be. Never mortgage your future on vibes and highlight reels. And for the love of everything holy, if you're going to commit a quarter billion dollars to a single human being, make sure that human being can still play the sport you're paying him to play.
No Fuchs Given.