From the looks of it, Reynolds still desperately needs a check
Ishod and GT will probably live happily ever after when they retire
Do you think their contracts are that good? I would think it also depends on the way people handle their money. You can loose a lot of money quick if you don‘t know how to invest it properly. I would think few people get wealthy from skateboarding and sponsorship deals. Only If you are smart with your money you can probably make that money last for a long time.
People set for life my dumb list:
Caballero (shoe)
Janoski (shoe)
Koston? Had a very lucrative Nike deal early on. But: Do you really need to take a job with the US skateboarding association if you are set for life?
Ellington (investment in craft beer company)
PRod (Early Nike SB Deal + Investment in craft beer company)
Mullen? Dwindle is not doing so well, but he got paid selling world industries
Heath Kirchart seems to be financially independent due to some investments and living pretty modestly
Obviously Tony Hawk is doing fine even though he was almost broke once during his career.
Tim O‘Connor seems to have done well for himself, no idea how though…