I don't mean it as a bonus, tho. Is there a creative way to sign a guy to a ridiculously long contract, beyond his potential to play in today's estimation and still fulfill the bindings of the NFL contract requirements? I mean if the Pats had known Brady would be playing after 20 years on from his first SB and had won a couple more, wouldn't/couldn't they might have figured out a way to keep the guy theirs forever with some creative contract back in 2004/5?
I mean if a player is signed to a 10 year deal, the team isn't bound to pay the damn thing off in 5 years. They could pay it all at year 10 if they chose, right?
So, Bobby Bonilla him. Sign him to play for 20 years and agree on amount to be guaranteed over that time.
So several problems I see...
1. If the player's under contract, that means he's either on your active roster (which means Lamar is taking up a 53 man roster spot 20 years from now) or he's not. If he's not, the dead money remaining on his deal becomes due essentially immediately.
So the moment Lamar retires, any remaining balance he has left on his contract becomes due, against the cap, immediately.
2. I'm not sure why you're stuck on this Bonilla thing. That works in MLB because MLB doesn't have a salary cap. Their business is almost entirely cash basis, and Owners will gladly defer salary for as long as the player will allow them to. Incredibly advantageous for Owners.
In a salary cap sport, I don't know of any mechanism where you can continue to charge cap hits for a player who retired several years prior.
Basically, in order to do what you want to do, you have to sign Lamar to a 20 year contract. But once he retires, that 20 year contract, from a cap perspective, shrinks to whatever the last year was.
I have no doubt that a team, could, theoretically, pay a player for 50 years if a player is willing to defer. But that's cash, not cap.
And by the way... I know a lot of the ignorant public likes to mock the Mets for still paying Bonilla. Those people, of course, are idiots. It's a home run idea for any MLB owner.
Basically it's like eating at Five Guys today, not paying, and paying the exact same price... only you pay 5 years from now. Owner gets to keep all the inflation, all the money, make interest off of it, etc., while the player gets nothing but his original agreement.
Only reason players would even consider it is because they don't trust themselves to not piss their money away.