Strong performances often lead players to sign massive contracts with new teams or secure lucrative extensions with their current franchises, turning them into multimillionaires overnight. However, those deals do not always unfold the way organizations hope they will.
One of the clearest examples of a costly mistake came with former Houston Texans quarterback Deshaun Watson, who moved to the Cleveland Browns in a blockbuster deal that the franchise continues to regret today, especially because the player remains tied to the organization.
In many cases, teams offer enormous guaranteed sums that are not always reflected on the field. It sometimes appears that once players secure their financial future, their level of performance declines, whether intentionally or not.
Franchises across the league have learned difficult lessons after committing huge portions of their salary cap to players who ultimately failed to deliver results worthy of their contracts.
Deshaun Watson and his arrival to the Cleveland Browns in 2021
In recent years, the most notorious example is undoubtedly the massive contract awarded to Deshaun Watson in 2021. During the 2020 season, the quarterback posted impressive numbers, throwing for:
- 33 touchdowns
- 7 interceptions
- 4,823 yards, leading the league in that category
There were strong reasons to pursue him at the time. Nothing suggested what would eventually unfold in the following years. Instead of becoming the cornerstone the Browns envisioned, Watson has spent more time dealing with setbacks than leading the team on the field.
His contract is worth $230 million fully guaranteed, and at least in the past two years, he has largely collected his salary while rarely seeing action on the field.
Russell Wilson with the Denver Broncos
The former Seattle Seahawks quarterback arrived in Denver in 2022 in a move that was widely viewed as unusual, to say the least. In exchange for Wilson, the Broncos surrendered a massive package that included:
- Two first-round picks
- Two second-round picks
- One fifth-round selection
- Three players
After the trade, he signed a contract extension worth $245 million, of which $165 million were guaranteed. The results of his tenure in Denver are now well known. His performance fell short of expectations, and he eventually ended up being traded to the New York Giants, where his struggles continued, and the move ultimately proved disappointing for another franchise.
Tua Tagovailoa with the Miami Dolphins
Tua’s performance with the Dolphins during his early seasons was spectacular, which led to a major contract extension in 2024. Both sides agreed to a deal worth $212 million, including $167 million guaranteed.
However, everything unraveled after the contract was signed. Tagovailoa endured a disastrous 2025 campaign, and his performance was widely criticized week after week.
Eventually, he departed Florida and moved to the Atlanta Falcons, where he now finds himself battling for the starting job against Michael Penix Jr.
Other players who failed to meet expectations despite receiving massive contracts include:
- Le’Veon Bell 2019
- Mike Glennon 2017
- Brock Osweiler 2016
- Bryce Huff 2024
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