re: Would you take $50 million tax free or $2 million/year tax free for life

What I would do:

Take the $50MM

Risk: I accidentally try to live like I make $50MM/yr in year 1, and go broke trying to keep up with my new yacht friends as a result of the severe reduction in cash flow year 2.

Risk management: I set up a (fairly) low risk mutual fund account with a $2MM/year withdrawal until it goes dry (hopefully never). This magical account adjusts every 10 years for inflation. I set up 7 different passwords, 25 characters each, that must be all entered correctly in order to change this setup. I do this by taking $1MM, going to Vegas, and having hookers and blow parties every day for a week, and each night at 5AM I enter a new password into the system without writing it down.