I seem to recall the TWolves doing something fishy along these lines with Joe Smith, they might have even straight paid him "under the table" or something similar...but they got nailed had to forfeit multiple picks. Not a good idea...and certainly not for a fringe guy like a Jagr.
Actually they didn't pay him under the table, they promised him a future long-term deal in return for some chea one-year signings. Generally these leagues would rather have you concuss Sidney Crosby or kneecap Lebron James than circumvent their precious salary caps.
Exactly. Teams aren't likely going to want to risk the penalties that could come with being caught circumventing the cap, especially in this case to sign a 40 year old Jaromir Jagr. Is it worth it to lose picks, have the organization fined, and I'm guessing if you got caught knowingly, the league is going to suspend the player as well.
Not to mention, I don't think it would be worth it for the GM because I would think it would hurt your chances of future employment. Being the guy responsible for a team losing picks and cash isn't going to endear you to owners.
In European soccer it's pretty standard for the owner of a football club to give players huge endorsement deals for their other companies, so that the debt won't be on the club's books.
It's not as meaningful, because financial fair play isn't enforced yet and probably won't ever be, but it really pisses me off.