I don’t know why stuff like this keeps me up at night but let’s pretend you just won some obscene amount and there’s a lot of people you’d like to set up for life. Let’s say after taxes you have $300m in your account

You can give someone up to 18k a year without incurring a gift tax and while that’d definitely be a nice bump to their income, you still have way more money than you know what to do with. So what’s the smartest way to hook them up?

A couple of options I’ve considered are:

1. Give them a lump sum of $X million. They eat the taxes the first year and handle the savings themselves.

2. Create a company and hire them to “work” one hour a month for a big salary. If you put $25m in an account, the interest covers the salary. They get a steady bonus income with the added bonus of getting the best insurance available. Is that legal?

3. Set up a “shared” checking account they can use to pay for…whatever. But would these expenses count towards the gift tax? I do not know.

4. Buy houses and let them live there rent-free. I don’t really like this one because I don’t want to be a lord to my friends and family.

For the record, I did not win the lottery. I don’t even play it. I’m just working out the details in a fantasy world for some reason