If I Were A Filthy, Stinking Rich Man

What I’d do with a billion-dollar lottery win

David Milgrim
4 min readFeb 14

I must admit that a billion-dollar lottery got my attention. We’re not talking about vacation money with first-class passage and conversations about how a million isn’t what it used to be. We’re talking filthy, stinking, unimaginably rich.

It refreshes the question I’ve always loved asking myself of what I would do with that money. Like, after I blow that first couple million that I’ve already allocated from countless imaginary lotteries where I was the sole winner. What, now, would the next 495 million after-tax dollars do for me?

The first thing that comes to mind is that this kind of money would buy me a deep sense of security.

Yet, the more I think about it, the more I doubt how much my own hook and ladder, backup heating system, or on-site, personal emergency room physician could really ease my lifelong propensity for constant panic.

With mega buckaroonies, I could hire a therapist to help me work on my perpetual panic. But I already see two therapists and I don’t know that another would really make that much of a difference.

I would at least have enough financial security to not have to work. The only problem there is that I like working.

I suppose I could do some shopping in stores I don’t typically frequent.

I do like buying stuff. But I’m already self-conscious about how much of it I have. After a couple additional guitars and a half dozen effects pedals from that first couple mil, I…



David Milgrim

Trying to feel okay, one comic at a time.