The Biggest Issue With the Ravens Isn’t Up for Debate and Has To Be Rectified ASAP

The Ravens’ inability to get Lamar Jackson extended to a new contract between last spring and this spring is, without question, their single biggest organizational failure. And their repeatedly awkward and misguided timing with the Hall of Fame quarterback certainly threatens the future direction of the franchise.

With Organized Team Activities looming, and an untested coaching staff in place (one that already made some regrettable comments about Jackson’s need to be at OTAS), and a roster that begs major questions on the offensive side of the ball, Jackson’s presence is paramount. And the task to secure his services beyond 2027 is everything.

And the way Ravens brass tiptoed around Jackson's presence at upcoming practices was quite a change in tone.

But in addition to making no headway on a completely reworked deal with Jackson prior to the start of the League Year, and instead opting to convert the maximum amount of salary to bonus for cap purposes, the Ravens also did nothing to sweeten the pot to incentivize him from attending most, if not all, of these looming voluntary spring practices.

Has The Best Time For A New Deal Already Passed?

The Ravens are at an unquestionably unique point in their organizational arc, one in which the front office carries more juice and currency than arguably ever before (despite a spotty track record of roster stewardship and contract acumen). And in this moment Jackson wields more leverage than ever before and he’s played the trade card already once before.

Going with a remarkably younger coaching staff, letting core players walk at key positions on offense and failing to extend rising talents to extensions certainly did not go unnoticed by the quarterback, and all carry risks.

Gambling markets – woefully wrong about Baltimore’s win total in 2025 – imply the Ravens have a strong chance to compete for a title. But they are walking a dangerous tight-rope with the greatest offensive talent in the history of the organization – a generational player at the most important position in professional sports – and it threatens to undermine any other gains they might make from a transactional standpoint between now and Week 1.

The fact they basically got nowhere with Jackson between January and April was quite telling, and once again the way this franchise has operated with this All-Pro quarterback is anything but the norm.

“Forget about the Crosby trade at this point; I think they did better with (signing Trey) Hendrickson, anyway,” said one NFL general manager. “The thing they should be getting killed for is pushing $40M of Lamar’s cap into future voidable years. The cap number for 2027 – his last real year – is $85M and the only way to get that lower is to get a real extension done. But what motivation does he have now, unless you give him whatever he wants? And if you were going to give him what he wants, why didn’t you do that by now?

“With the no-trade clause, and the no-franchise-or-transition clause, they’ve given away every ounce of leverage possible to get him extended. What they’ve done really takes away any bit of leverage they might have had, and it actually makes him easier to trade.”

Lamar keeps a truly close circle; after negotiating a tremendous contract last time around that’s not going to change. For what it’s worth, chatter around the scouting combine was that Jackson didn’t seem motivated to engage much with Baltimore (strategy worked well in the past!), and, well, he knew as well as everyone once what the Ravens would have to do if he didn’t agree to a new deal – push that $85M into 2027 and put the franchise even more under the gun to get him extended in the next 11 months (before the start of the 2027 League Year).

He had to play for peanuts way longer than ever made sense on his rookie deal, he was plenty willing to stick to his stance and wait out the Ravens before he had even made generation NFL money. Now that he’s made it, he’s continued to post MVP campaigns under two offensive coordinators.

So there’s no reason to think he is sweating any of this. And, quite possibly, not sweating these upcoming fake football practices, either. Whether he is there or not, failure to maximize the time before the draft – and thus before the window to get 2026 assets for Jackson just in case he requests another trade – to secure a new deal would be yet another considerable misstep. The riskiest of all to this point.

“I’m not sure you can say it’s unprecedented, but quarterbacks of this stature, at this stage of their career, don’t usually reach the penultimate year on their contract without a new deal already in place,” said one longtime NFL contract negotiator who executed several massive QB extensions. “Maybe they’ll get it done with him before the season, but after this restructure, with the new guarantees, Lamar has even less motivation to do anything and even more leverage than he had before they redid the deal and pushed the ($84M) cap to 2027.”

If Jackson makes it to Week 1 without a new deal, there isn’t anyone in the industry who seems convinced he would still be in Baltimore by Week 1 of 2027. When the sides agreed to this deal in 2023, agents and execs who studied the contract anticipated a major alteration prior to the 2025 season, with how fluid and soaring the QB market is.

The Ravens have perpetually held back from getting Jackson’s deals done on the expected timeline. And they only cost themselves for it. And it’s already happening again. Time keeps wasting and the costs keep soaring.