The Ravens have made it clear: they want Lamar Jackson locked in beyond 2025. The franchise quarterback is entering year two of a five-year, $260 million deal. But that hasn’t stopped internal talks of a potential extension. Per The Athletic’s Jeff Zrebiec, the team “would love” to get a new deal done before the season kicks off. The motivation? Avoid another drawn-out negotiation cycle, like the one that nearly pushed Jackson out the door in 2023.

There’s also the math. Jackson’s $43.5 million cap hit for 2025 will balloon to $74.5 million annually over the final two years of the contract. The Ravens know they’re nearing a crossroads. Head coach John Harbaugh hinted at it back in March: “That’s going to continue to have to be addressed… Lamar is the main part of that because he’s the franchise player.”

Harbaugh didn’t dance around expectations either: “When Lamar gets paid, he’s going to be the highest-paid player in football.” Basically, if the Ravens want to reset the deal, they better come prepared with a number that reflects that.

But while the front office tries to get ahead of the situation, Jackson seems to be stuck in the last chapter. Over the weekend, the 28-year-old quarterback posted a cryptic Instagram story that didn’t go unnoticed. “Once I show my love they show me why they don’t deserve it, right then soon as I put my guard down that’s when they hurt me.”

It was one sentence, with no names, but for anyone following the contract chatter, the message landed with weight. Emotionally bruised and financially cautious, Jackson appears to be sending a very public signal: he hasn’t forgotten how the last negotiation went.

That last round lasted nearly two years. It ended in April 2023 with a deal, yes! But not before Jackson requested a trade on social media. That friction wasn’t just about numbers. It was about timing, trust, and the aftermath of Deshaun Watson’s fully guaranteed $230 million deal that reset the market in 2022.

Jackson didn’t have an agent. The Ravens didn’t blink. The standoff was deeply personal, and even with a deal signed, the scars haven’t fully healed. What complicates matters now is the shifting quarterback market. Baltimore has choices to make. The next few months will reveal whether the organization can re-earn Jackson’s trust. Or risk watching old wounds reopen at the worst possible time.

The Ravens must think in the Lamar Jackson direction before it’s too late

Look around the league: Brock Purdy just inked a five-year, $265 million extension. Yes, the one and truly Mr. Irrelevant. Well, he’s got the last laugh now, at least on someone like Lamar Jackson. And while his story is one for the ages, it’s what the Ravens haven’t done yet that’s getting louder. For a quarterback once dubbed the highest-paid in football, Jackson’s deal now looks way outdated. He ranks 10th in annual value. You think he hasn’t noticed?

Now, the Ravens did recently clear $30 million in cap space. On paper, it looks like good business. But if you’re Lamar? That probably didn’t feel like a warm hug. Some saw the move as a way to pave the road for a new extension. Others—and maybe Jackson himself—saw it as Baltimore prioritizing flexibility everywhere else.

The thing is, the league’s pace isn’t slowing down. Dak Prescott’s $60 million average? That’s the going rate now. Purdy’s deal only adds pressure. And if the Ravens wait too long, Jackson’s $74.5 million cap hits in 2026 and 2027 will loom like a blitzing edge rusher. No one wants to restructure with a ticking financial bomb.

Baltimore says it wants to keep Jackson. That it’s not a matter of if, but when. Each passing day shifts the leverage a little more. The longer they wait, the more expensive the future becomes. If the Ravens want to lead with Jackson, they need to start acting like it before someone else gives him a reason to feel wanted again.