Colin Cowherd, on a recent episode of The Herd, made one thing pretty clear: as much as he supports Lamar Jackson, he’s not sold on the Baltimore Ravens pushing for another contract extension. In his view, the Ravens aren’t really in the Super Bowl bubble right now. And for specific reasons, he believes Lamar’s contract situation, along with his family’s involvement as his manager, plays a significant role in that equation.

“I’ve always been a big fan of Lamar Jackson,” Cowhered stated, “but between his mom acting as his agent, his refusal to do offseason camps, the mystery injuries, and let’s be honest, the need to be the highest-paid quarterback, that’s the thing he wants to be, it started to feel like, honestly, a little Kawhi Leonard. Mercurial, mystery, family too involved, maybe.”

Jackson is currently signed for two more seasons with Baltimore. The organization, however, appears eager to extend its franchise quarterback sooner rather than later. That urgency is exactly what Cowherd questions. And his concern has little to do with Lamar’s talent.

Jackson represents himself in negotiations, but his mother, Felicia Jones, has acted as his adviser and manager since he entered the league. That setup has drawn criticism around the NFL. At the same time, it has undeniably worked financially.

For context, Jackson agreed to a five-year, $260 million deal with the Ravens, a contract negotiated without a traditional agent that made him the highest-paid player in the league at the time. Still, Cowherd has consistently pointed to other factors, particularly Jackson’s offseason participation.

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In 2022, Jackson skipped voluntary OTAs for the first time in his career. In 2023, he missed the start of those workouts. Then, in both 2024 and 2025, he again missed most voluntary sessions and forfeited workout bonuses. Add the reported hamstring issues in 2025 that led to missed practices, and Cowherd sees a broader pattern.

Now, with Jackson seeking another extension, Cowherd explains why he remains skeptical. Lamar is set to count roughly $74.5 million against the salary cap this season. If the Ravens aren’t firmly in the Super Bowl tier, Cowherd argues, committing even more financially could further limit roster flexibility.

He emphasized that a $74 million cap figure could fund multiple core players elsewhere. As an example, he noted that the Seattle Seahawks (fresh off a Super Bowl) could theoretically pay Sam Darnold, Jaxon Smith-Njigba, Devon Witherspoon, Nick Emmanwori, Grey Zabel, and DeMarcus Lawrence with that type of money and still have room left over.

The point wasn’t literal accounting. It was about allocation.

And his argument doesn’t exist in a vacuum. Several of the league’s highest-paid quarterbacks in recent seasons, Aaron Rodgers, Dak Prescott, and Joe Burrow, among them, have not delivered Super Bowl titles. That’s the larger financial caution Cowherd is hinting at.

Whether that logic ultimately influences Baltimore is another matter. The Ravens appear committed to Lamar long-term. If anything, signs still point toward another major extension.

The Ravens are confident in extending Lamar Jackson’s contract

For now, Lamar Jackson carries the second-highest cap hit in the league at roughly $74.5 million. Meanwhile, Ravens general manager Eric DeCosta has made it clear he’s confident a new deal will eventually get done with his two-time MVP quarterback.

“Lamar and I have an agreement [that] we handle business kind of in-house internally,” DeCosta said at the NFL Scouting Combine. “That worked well for us the last time and we will continue to have that policy moving forward. I have spoken to Lamar about a lot of different things over the last month. He’s been very engaged. … We’ll continue those conversations moving forward.”

Reading between the lines, an extension feels more like a matter of timing than possibility. Still, if the two sides don’t finalize something by next month, a restructure becomes the practical short-term move. With the new league year beginning March 11, Baltimore will want added cap flexibility before free agency opens.

One option would be converting a significant portion of Jackson’s $51.2 million base salary into a signing bonus. That would lower his immediate cap hit and free up space now. However, it would push more money into 2027, the final year of his current deal, increasing that future cap number.

The last time Jackson signed an extension, he became the highest-paid player in the league at that moment. Whether history repeats itself, and whether he reclaims that financial crown, is what makes this next stretch before free agency worth watching.