The Bears signed No. 1 overall draft pick Caleb Williams to his rookie contract today, and we’ve already reported on a number of intriguing negotiation tactics utilized by Williams throughout this process. These include the lack of an NFLPA-certified agent, opting instead for a “board of directors” approach, and the quarterback’s aim to secure a no-franchise tag clause in the deal. 
According to Mike Florio of NBC Sports, though, these weren’t the only tactics Williams pursued. After already trying to set new precedents with the no-franchise tag clause, Williams reportedly also attempted to break new ground on how his rookie salary will be taxed. Williams’ father has experience working in commercial real estate, providing his camp with unique insight into tax law.
One of the attempts employed by Williams’ camp reportedly tried to get Williams paid as an LLC. As a corporation, Williams would face different tax laws than those of an individual. While the league’s Collective Bargaining Agreement doesn’t appear to have any stipulations limiting this approach, the NFL ultimately made the overarching call to deny Williams, telling the Bears that a player’s money can’t go to a business entity other than the individual.
A second approach saw Williams attempt to model his rookie contract payments after a forgivable loan. In this scenario, Williams could have received the money tax-free until the loan was forgiven in as many as 10 years. Once again, through the league’s advice, Chicago ultimately turned down this option, as well.
Other rumors suggest a situation in which the contract would’ve included “language that will void future guarantees,” bringing up questions of whether or not the Bears would be entitled to receive an offset should they release Williams with guaranteed money remaining and he signs with a new team.
Credit where credit is due, Williams and his crew were extremely creative in their attempts to maximize the value of Williams’ new source of income. The Bears appeared to be willing to play ball but were time and again blocked by the league. While unsuccessful in these attempts, Williams may have opened the door for future first-round picks to have more grounds for negotiation in their rookie contracts.