Friday, May 22, 2026

Caleb Williams’s Contract Requests Could Have Changed the NFL

  • Williams ultimately agreed to his rookie-slot deal with the Bears on Wednesday.
  • The league vetoed several creative proposals to avoid taxes.
Kamil Krzaczynski-USA TODAY Sports

Last year, Caleb Williams’s father, Carl, broached the idea of his son getting equity in the team that drafted him. That never became part of Williams’s contract negotiations, because the NFL went on to pass a rule barring players and other team employees from receiving ownership stakes in their teams. 

But as his negotiations with the Bears dragged on—the sides finally announced an agreement Wednesday—several unique requests leaked out. The team and league shot them down, but they still show the Williams family’s creative approach to mostly rigid NFL contracts.

At least three groundbreaking requests from Williams’s camp were reported by Mike Florio in a pair of stories this week.

  • Williams wanted to get paid as an LLC, which would have avoided taxes in Illinois.
  • He also asked about getting paid through a forgivable loan, which would have had the same result.
  • He requested a no-franchise-tag clause, which no rookie has ever received.

The league ultimately decided that the first two were impermissible, despite no explicit prohibitions on them in the collective bargaining agreement, according to Pro Football Talk. The Bears rejected the third request.

Who was doing the asking, and how, remains up for debate. Last week, when Williams was still unsigned, he told the Chicago Tribune it was out of his hands.

“I’m not handling that,” Williams said. “My lawyers and attorney and everybody, the head of the Bears, everybody up there up top is handling that. That’s not my position that I’m handling.” But Williams has no NFLPA-certified agent, and teams are not permitted to directly negotiate with any other player representatives. In the end, that may have been the bigger holdup in Williams actually putting pen to paper on his four-year, $39 million rookie deal. Florio, who has been all over the story, reported what “they’re getting into is a situation where the lawyer who’s handling this isn’t as versed in the nuances of the contract as an experienced and competent agent would be.”

Although Williams’s requests and lack of an agent were unusual, going deep into the summer unsigned while haggling over language is not—even for rookies, who mostly have the leverage to negotiate only over offset terms. Williams’s Bears teammate Rome Odunze just agreed to his deal Tuesday. And in his own division, Vikings first-round picks J.J. McCarthy and Dallas Turner remain unsigned as of Thursday morning. 

This field is for validation purposes and should be left unchanged.

Sign up for
The Memo Newsletter

Get the biggest stories and best analysis on the business of sports delivered to your inbox twice every weekday and twice on weekends.

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.
Linkedin
Whatsapp
Copy Link
Link Copied
Link Copied

What to Read

Charlie Pilner and Nikolas Rohrmann

How 2 Brown Undergrads Became Sports Deal Brokers

An experimental project turned into a permanent course and business deal network.

Fever Get Warning, No Fine Over Caitlin Clark Injury Report

A WNBA source confirmed that they were not fined.
Dec 21, 2024; Austin, Texas, USA; A view of the CFP logo and SEC logo before the game between the Texas Longhorns and the Clemson Tigers in the CFP National Playoff First Round at Darrell K Royal-Texas Memorial Stadium. Mandatory Credit: Jerome Miron-Imagn Images

SEC Holds Cards to 24-Team College Football Playoff

CFP expansion will be a major topic at the SEC spring meetings.
U.S. Senator Richard Blumenthal (D-CT) speaks with the press after the Republican-controlled U.S. House of Representatives passed bipartisan legislation to fund Department of Homeland Security agencies including the Secret Service and Transportation Security Administration in a move to end the partial shutdown that has gripped their operations for nearly 11 weeks, on Capitol Hill in Washington, D.C., U.S., April 30, 2026.

Critics Warn Kalshi and Polymarket Risk a Juul-Style Reckoning

Their advertising methods came under fire from lawmakers this week.

Featured Today

NFL Rivalries Are Made on the Field, Mocked in Schedule Release Videos

Every year, teams find new ways to one-up themselves (and their rivals).
Bart Swings/Falyn Fonoimoana/Avery Poppinga
May 14, 2026

OnlyFans Is Paying Pro Athletes What Their Sports Won’t

The adult-content platform is a reliable income source for niche athletes.
May 13, 2026

How Sports Graphic Designers Are Grappling With the Rise of AI Art

The release of ChatGPT 2.0 Images sparked a conversation among sports designers.
May 12, 2026

Collectible Cups Are Sending Sports Fans Into a Frenzy

The drink is secondary to the wild vessel it comes in.
Sponsored

Volpe Brings Style to the Bronx

With the New York Yankees & Anthony Volpe, Charles Tyrwhitt is bringing its decades-long playbook to one of sports’ biggest stages.
May 12, 2026

NBA Player Brandon Clarke Dies at 29

Clarke died on Monday in Southern California, authorities say.
May 15, 2026; Newtown Square, Pennsylvania, USA; Bryson DeChambeau plays his shot on the seventh tee during the second round of the PGA Championship golf tournament.
May 15, 2026

Bryson DeChambeau Misses Second Major Cut Amid LIV Turmoil

DeChambeau also missed the cut at this year’s Masters.
Sponsored

Mark Cuban Peels Back the Curtain

Mark Cuban discusses sports ownership, the rise of NIL, and the evolving media landscape.
May 12, 2026

Another Summer of LeBron Is Here

James is not under contract for next season.
Aug 2, 2024; Nanterre, France; Benjamin Proud (Great Britain), Cameron McEvoy (Australia) and Florent Manaudou (France) in the men’s 50-meter freestyle medal ceremony during the Paris 2024 Olympic Summer Games at Paris La Défense Arena.
May 11, 2026

The Enhanced Games Want to Be More Than a Steroid Olympics

“There’s a benefit for anyone to live enhanced.”
Trick Williams Front Office Sports
May 9, 2026

WWE’s Next Big Star Could Be Ex-NFL Hopeful Trick Williams

The former South Carolina wideout is now WWE’s U.S. champion.
May 6, 2026

Napheesa Collier Admits Engelbert Rant Was For CBA Leverage

The WNBA and WNBPA agreed to a new labor deal in March.