The current dispute between the Las Vegas Raiders (“Raiders”) and Christian Wilkins (“Wilkins”) is more than a football headline; it underscores how fragile the concept of “guaranteed” money can be—not only in sports but also in entertainment law more broadly. Whether you’re an athlete, artist, or entertainer, guarantees are only as strong as the language in your contract and your compliance with the terms.
This legal tension reveals a critical need for athletes to understand precisely how “guarantees” actually function in professional sports contracts. In the NFL, the term “guaranteed” is far from absolute. Rather, it is qualified by specific categories that determine how and when a player remains entitled to payment after being released. In order to appreciate the stakes of the Raiders-Wilkins dispute, it is essential to examine the structure and conditions of guaranteed money in NFL contracts. For instance, NFL contracts offer three types of guarantees: (1) Skill, (2) Cap, and (3) Injury.
- Skill guarantees: if a player is released because his team does not believe that he has the requisite skill comparable to others on the team at his position, he is still entitled to money guaranteed under this concept;
- Cap guarantees: if a player is released so that his team remains under the salary cap, signs a free agent, or re-signs a current player, he is still entitled the money guaranteed under this concept; and
- Injury guarantees: if a player is released but is currently unable to perform football duties as a result of team activities, he is still entitled to the money guaranteed under this concept. This is the most common type of guarantee.
The third guarantee is particularly relevant in the Wilkins’ dispute – specifically, the term “as a result of team activities.”
On July 24, 2025, the Raiders released Wilkins, whom they previously signed to a $110 million deal in March 2024 that included injury guarantees. Wilkins suffered a Jones fracture in his left foot during the 2024 regular season and underwent surgery, which ended his 2024 season. He began the 2025 offseason on the Physically Unable to Perform (PUP) list. Reportedly, the team claimed that Wilkins needed a second surgery, which Wilkins allegedly refused.
Ultimately, the Raiders assert that his release was due to a “failure to maintain his physical condition to play.” They issued the following statement:
“We have decided that it is in the best interests of the organization to move on from Christian Wilkins and he has been informed of his release from the team. This franchise has a Commitment to Excellence on and off the field. With no clear path or plan for future return to play from Christian, this transaction is necessary for the entire organization to move forward and prepare for the new season.
(Emphasis added).
The Raiders now argue that Wilkins’ condition does not fall under “injuries from team activities” because he did not follow his prescribed rehab plan. Based on this action, the Raiders are attempting to void $35.2 million in injury guarantees contained in Wilkins’ contract.
Wilkins, supported by the NFLPA, has filed a grievance and a legal battle is anticipated.
This case serves as a timely reminder that even so-called “guarantees” in high-stakes contracts are subject to interpretation, litigation, and “loopholes.” Whether in sports, music, or film, contractual guarantees only offer protection when (i) they’re carefully drafted; and (ii) when both sides uphold their obligations.
And in those inevitable moments when disputes arise, as they often do in complex, performance-based industries, it becomes increasingly important to have experienced legal counsel who not only understand the intricacies and nuances of guarantee structures but who are also deeply familiar with the grievance procedures that may ultimately determine enforcement. A contract’s value lies not just in what it promises on paper, but in how effectively those promises can be defended when challenged.
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