Arguably he could borrow against his annuity and save on taxes with loans. He could also setup a charity in which he donates a max amount and set up family on the board avoiding other taxes and making write offs as if he is ceo he can buy company property stuff that he can write off too.

I wouldn't use the most aggressive numbers on that, I'd plan for 5 percent. Which is 20 million but then you also have capital gains tax. After which you'll have 15 million a year instead of 14 million a year. The annuity also generally comes with a larger total payout though. So in reality it'll be higher than 14 million.

So yes you can get lucky in the stock market to beat an annuity, but that's not the reason people get told to take the lump sum. Most lottery payouts are 100k or less and 10k a year isn't going to do much, while 100k starts a retirement fund. Once you're high enough that the annuity itself is "quit your job money" it flips. Then if you screw up you know you're getting back on your feet next January.