This Is How I Would’ve Spent My Nonexistent Powerball Winnings

Michael Gregg
Michael Gregg is 23 going on 80. His interests include pre-1980s music, brown alcohol, and making relationships complicated. He hopes to one day be the host of The Dick Cavett Show.

I’ve always been against the lottery on an intellectual level. It amounts in practice to a tax on dreamers, depriving the hopeful of money that would be better spent on lunch or a pack of cigarettes. Though it’s promoted as a way to funnel money towards education, I’ve never seen convincing evidence that legalized, government-administered gambling has done much to improve the educational standing of America’s youth. These, and other reasons (aka I have literally no money), led me to abstain from the recent Powerball drawing.


Since seeing that nice couple and their dog on TV celebrating their big win, however, I’ve developed an acute case of non-buyer’s remorse. Though they seem like nice folks and all, I just get the impression that I would make a much better lottery winner. Now don’t get me wrong; by “better,” I certainly don’t mean “more philanthropic” or “more conservative in my investments.” I just mean I’d have more fun, zany, irresponsible, and morally questionable things to do with the money than “pay off my mortgage” and “buy a horse.”


First order of business would, of course, be letting the money go straight to my head. The second that check clears, I start burning bridges — friends, family, colleagues, nice baristas, they can all go cry their poor eyes out. I’m currently living with my parents, so I’d take a chunk of that cash and send them off to a home (they’re only in their mid-50s, but money opens doors, so to speak). But who would settle for their current living situation with 800-million-some-odd dollars sitting pretty in their bank account? I’d buy myself an immaculately preserved 19th century brick row-house in the nicest part of town, park-adjacent, and hire my former friends as the help. They say money can’t buy happiness, but I think the image of my buddy Dave in a French maid outfit picking up dog shit comes pretty close.

A boat would definitely be in order, too, and none of that nouveau-riche yacht nonsense. I’m thinking something pirate-y, with both working cannons and a sweet-ass sound system. And I guess I’d need a crew, too, so there’s another million spent on one-legged dudes with sailing experience.

Of course, my wardrobe would get some upgrades as well. I’m currently rocking the 80-year-old college professor look, but I think once you have at least $100 million, you’re legally required to start dressing like Prince. I guess that’s a philanthropic use of my money; I could single-handedly revitalize the purple crushed-velvet blazer industry.

Some plastic surgery would be nice, too. Liposuction, of course, but I imagine with an unlimited budget, I’d get real weird with it. Michael Jackson already perfected the “look like a Diana Ross serial killer” angle, so maybe I could look like another 70s disco star? I bet I’d make a pretty convincing Dolly Parton with the right doctor at the helm, and they could use the leftover fat from the liposuction to give me oversized tits.

Once all that is complete, I’d have to find a hobby and go full-on Howard Hughes with it. Maybe I could buy a niche sport, like Jai Alai or disc golf. Barring that, I’ll just piss the rest of the money away on bad inventions and cocaine.


I guess, on second thought, this nice couple from Tennessee should probably keep the money, and I’ll just go on recycling cans and working on unpaid writing gigs. C’est la vie.