The Expert Who Helped Lamar Jackson Negotiate His Last Ravens Contract Believes End Could Be Near

Almost no one was privy to the inner-workings of the Ravens’ long-and-arduous contract negotiations with Lamar Jackson, dating back to 2020, with an MVP already to his name, once eligible for his first contract extension.

General manager Eric DeCosta, now having quite a miserable time building a sustained winner, led the charge on a process that would take years to complete and was unlike any other first-time QB extension for a superstar in NFL history. It would include a non-exclusive franchise tag and trade demand and collusion case along the way. DeCosta was aided by cap chief Nick Matteo – who has authored some of the ugliest contract structures in the NFL in recent years (hence the worst cap situation in the NFL) and team president Sashi Brown, once he took over for legendary steward Dick Cass after he retired.

As for the other side of the table, it was and still is just Lamar Jackson and his mom.

No agent. No marketing guru. No other voice.

And Jackson was seeking counsel from DeMaurice Smith, head of the NFLPA at the time, and Mark Levin, who for roughly 25 years oversaw the Salary Cap and Agent Administration department of the union, in charge of regulating agents and helping them negotiate deals and serving as the PA’s foremost expert on the Collective Bargaining Agreement that governs economic engagement between labor and management.

Levin was Team Jackson’s de-facto agent in the process and a beacon available to them to discuss comparable contracts around the league and structures and guarantees and intricate language. He was available on the other end of the Zoom when they wanted to mull no-trade clauses and no-franchise tag clauses (both of which they successfully obtained) and when they got an $84M poison pill cap charge for 2027 (with a $75M dead cap) that effectively makes Jackson a free-agent after the 2026 season.

Levin was as plugged in on cap and contract matters are anyone on the planet for a generation, and even after retiring from the NFLPA last year, top agents seek his counsel regularly and he assists many more formally as head of Pro Football Consulting. Before taking over the salary cap department at the NFLPA, he oversaw the salary cap and contract negotiations for the Washington Commanders and understands these matters from all perspectives.

He’s continued to follow Jackson’s ongoing saga with the Ravens closely, and their inability to make even a modicum of headway on getting him extended to a new deal back in March of 2025, when it was imperative on the heels of Josh Allen’s extension in Buffalo. Levin predicted basically everything that was to come this summer and fall when he joined me on “The Daily Flock Show” in May to analyze Jackson’s stalemate with the Ravens.

So, with Jackson injured again and the Ravens noncompetitive without him, with a bloated roster that should have been purged before the trade deadline and one of the worst offensive lines and some of the least-proven overall offensive talent in the NFL looking forward, Levin has a strong feeling about what’s next between this two-time MVP, and the Ravens.

What’s Next?

Oct 4, 2026; Baltimore, Maryland, USA; Baltimore Ravens quarterback Lamar Jackson (8) sits on the bench after being removed from the game due to a possible injury during the third quarter against the Tennessee Titans at M&T Bank Stadium. Mandatory Credit: Tommy Gilligan-Imagn Images | IMAGN IMAGES via Reuters Connect

Levin knows these individuals quite well and how they operate and was inside these talks and how personal it got at times, unlike almost anyone else on the planet. Like other experts who have discussed this matter with us, it seems obvious to Levin that Jackson will command $70M a season or more, with massive guarantees (even despite his injuries; didn’t impede Dak Prescott, for instance), and Jackson can and will call his own shot in regard to where he plays.

“I would be surprised if he's on the team next year,” Levin told me on “The Daily Flock” this week. “I'd be surprised … Unless the Ravens change their course and agree to make him the highest paid or the second highest paid quarterback on a on a legit structure, legit deal - not with a lot of fluff and window dressing - I just don't see him on the roster next year.

“I think they're just going to have to, you know, for the Ravens’ sake, hopefully trade him and get some good compensation for him, as opposed to just outright cutting him and not getting anything. But I just don't see him on the roster this year. And I think that, based on what's happened this year, you know, it might be time for the Ravens fans to buckle up … and look at a rebuild. They're in a bit of a pickle.”

I’d put Levin’s assessment of the situation up against anyone’s.

Jackson has simply smiled and check-mated the Ravens all along, DeCosta reverted to a trite talking point about being “optimistic” about signing Jackson before the season even as the QB spurned him again, and if the Ravens haven’t paid him what it would take to secure his services by now, it’s beyond fair to suspect they might never again.

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