Agree. He's already cost himself millions he'll never get back
Very possible he has. But he also gave him self a chance to max it out. That's the constant trade off, you either decide to lock in as much as you can up front or you gamble by going year-to-year which either allows you to maximize your earnings or you could end up making less.
I heard a comparison to Josh Allen today in terms of cash made to date, saying that this is money Lamar can never make up, and its a really bad argument.
Firstly, Allen's rookie deal was worth about $12M more than Lamar's based on draft position, $21.4M to $9.4M. No decisions by either one of them led to that. Through their first 3 years, Allen had been paid $17.9M compared to $7.7M for Lamar. That's $10M Lamar was behind but not because he or anybody did anything wrong. Allen signed at that point, an extension that tacked 6 years onto the remaining year plus 5th year option on his rookie deal. Obviously Lamar hasn't gone that path. In the two years since, Allen has gotten paid $67M in salary and bonuses. Jackson has made $24.8M in these two seasons on his final year and 5th year option. So that's about $42M less to date for Lamar because of his decision to not extend after 2020. That's huge. But it would absolutely be made up entirely, if Lamar signs now.
Between salary and bonuses, Allen will earn $1.58M (not a typo) in 2023, $30M in 2024, $39.5M in 2025, $38.5M in 2026, $40M in 2027, and $41.5M in 2028. As of now, only $47.08M of those payouts are guaranteed (all 2023 & 2024 money), the rest of the $191M is not guaranteed. All numbers from overthecap.
So if Lamar signed today for 6/$235M, with $90M guaranteed, he'd end up ahead of Allen until/unless Allen signs a new deal. Does anyone doubt that Lamar has been offered such a deal? The reported deal from the Ravens was for more total and guaranteed dollars and was only over 5 years.
Fair to say Lamar is making a mistake by not taking the biggest deal he's been offered by the Ravens. It was a huge offer. But its flat wrong for people to say that Lamar will never make back the money he hasn't earned that Allen got because he decided to sign. That ignores the obvious huge lump sum of the bonus that comes with such deals. Lamar will earn enough on a new deal to more than make up for the current gap between he and Allen in career earnings.