With respect to the OP, I think certain things can be done if you're careful about it.
If you have a super tight relationship with a player, then you could probably set up an investment or business with a good family member of his and keep it quiet.
Another possibility is if a player is nearing the end of his career in a few years, you could promise them a business or something.
The much maligned DeBartolo did exactly that for Jeff Fuller in 1989, except it wasn't to circumvent the cap or anything -- he suffered a career ending injury and wanted to make sure he would be financially taken care of since he was never a high paid star player nor was there any guaranteed money waiting for him.
If it weren't for having to pay taxes on luxury goods, you could just give players houses and cars to supplement income.
If you have a super tight relationship with a player, then you could probably set up an investment or business with a good family member of his and keep it quiet.
Another possibility is if a player is nearing the end of his career in a few years, you could promise them a business or something.
The much maligned DeBartolo did exactly that for Jeff Fuller in 1989, except it wasn't to circumvent the cap or anything -- he suffered a career ending injury and wanted to make sure he would be financially taken care of since he was never a high paid star player nor was there any guaranteed money waiting for him.
If it weren't for having to pay taxes on luxury goods, you could just give players houses and cars to supplement income.