Micah / January 5, 2011 8:14 AM

Have you ever listened to that This American Life about the guy whose job it was to buy lottery winnings for pennies on the dollar from people who had gotten themselves into serious financial trouble after winning the lotto? I think it's in that story that they cite a statistic that says the majority of lotto winners actually regret winning, because they ended up acting insanely irresponsibly with the money, and it caused them a ton of misery.

So I'm taking that money, buying a new camera, maybe a new bike, probably a house, giving a bunch of it away. And then I'm sitting on it. Because I don't want to be one of those people who regrets winning $330 million.

Charles / January 5, 2011 8:37 AM

Enjoy it with someone special. I would of course donate a considerable amount of it too.

mary s / January 5, 2011 8:42 AM

first and foremost, definitely throw one hell of a party. you're all invited. then i think i would gift each of my family members something (stocks?), buy a house, then donate half of the remaining sum. i would also sit on whatever was leftover.

bob / January 5, 2011 8:57 AM

pay off all my friend's school loans, credit card bills and mortgages). maybe buy my goofball siblings small homes/condos. lots and lots of charitable donations. lots and lots of travel.

shechemist / January 5, 2011 9:02 AM

I'd hire an accountant, an investment firm and an auditing firm to go over the books once or twice a year.

After that I pack up my family for 4 to 6 months in Spain to learn Spanish and decide what to do next.

I would set up an endowment scholarship fund for my parish's school.

And I would totally tell my place of employment to suck it, and suck it hard.

Dennis Fritz / January 5, 2011 9:22 AM

Donate it it--every damned cent of it--to the Hare Krishnas.

dkf / January 5, 2011 9:40 AM

I would buy every empty lot and boarded-up building in Chicago. Then I would plant trees and gardens in the empty lots and rehab the buildings into affordable (but nice) housing.

I don't know if $330 million would be enough, but I'd start on the South Side where property is a lot cheaper.

annie / January 5, 2011 12:33 PM

@dkf - that's nice, but it would never happen. The city actually tries to get tax payers on those empty lots..I'm just saying.
I would start a Foundation and work on projects that move me, I'd start with small business incubators...this is after I bought myself a sweet pad in NYC!

Raluca / January 5, 2011 1:45 PM

Fund research how to cure viral apathy, throw a ridiculous party and go for a week to Capetown :)

dkf / January 5, 2011 1:46 PM

@annie, I don't know what you mean. I would buy the property -- and pay the taxes on them. I don't have a problem with paying taxes.

R / January 5, 2011 2:08 PM

I would call my siblings up and tell them to assemble their bills and get on a plane for a swank trip to Hawaii (as in, staying "where Barack stays" kind of trip) for a week or so.

After making sure their debts are settled, I would arrange college tuition for all of my nieces (and future kids, if/when applicable) and figure out how all of our lives could be easier with the money.

For me? I'd like to have a bigger place for taking in shelter dogs. I'd also like to buy a place in NY and San Fran, and basically spend my time shuttling between here and there to get my fun on.

Mike / January 5, 2011 3:11 PM

I'd let the money go to my head. My family and friends would be overcome with greed and would eventually come to hate me because I wouldn't give them as much as they'd feel they deserve. I'd destroy any remaining personal relationships due to my own greed and inability to remain a mature and trustworthy person -- since I could have literally anything I want. Every possible fantasy would be there for me to experience. Eventually I'd become numb to it and nothing would thrill or excite me. I'd seek to escape in booze or pills and would develop a substance abuse problem and come to hate myself. Eventually I'd be miserable, penniless and alone. I'd regret winning the money and everything it had caused me to do. My life would descend into a plummeting spiral of despair and horror. I'd wake up each day in the late afternoon with the terrible realization that it had not all been one of those terrible nightmares and I was so happy to be just goofy Mike with his great girlfriend, loving parents and cool sister and friends. Nope, I'd realize it was all real and it was still happening, everything had been so quickly ruined, and I only had myself to blame. Finally I'd end it all myself. A pathetic, shameful waste, all brought on by material greed.

And I'd get a vintage 1965 pre-CBS Fender Jaguar.

Spook / January 5, 2011 3:25 PM

Wow, what an original and imaginative question!

Team Spook and I would travel to Morocco or the Niger Valley and collect DNA samples from a six foot tooth of a Spinosaurus!

We would then replicate a live Spinosaurus!

I'd air lift her/him back to Chicago and land right in the middle of a Cubs game for a "snack"!

But before hand I would have selected musicians to update the song "The Monster Mash" with
"The Spinosaurus Mash" to be played on huge but light weight speakers(design by NASA) looped around the Spinosaurus's neck, tail, and legs. Then with
"The Spinosaurus Mash" blasting, we'd wreck Chicago, chewing up more people that I don't like, which would mean lots of blood and guts turning the streets red! I'd probably take out much of the midwest, sparing only inner city Detroit and places like Gary, Ind. I'd probably also take out places like LA, Las Vegas, both Disney Worlds, etc. Power centers in Washington would also have to go.

Adam / January 5, 2011 3:58 PM

Run for Mayor. Platform: $100 for every Chicagoan.

Brubeck / January 5, 2011 4:28 PM

Basically, my life would remain the same as it is today, except all the bank accounts and all the bills would have a few extra zeroes at the end.

I'd probably work miserably at trying to keep my wife from spending all the money on a bunch of useless crap that she just had to have because it was 50% off. I'd have to buy a large house with enough room to contain all this useless crap. All this useless crap would collect dust, while she's elsewhere buying more useless crap that just sits around and is never utilized.

End of story.

three / January 5, 2011 4:39 PM

spend 1/3, donate 1/3, save/invest 1/3

jen / January 5, 2011 5:31 PM

buy a place that needed rehabbing and set aside enough to rehab it, along with a few new furnishings (I'd love a new bed); pay off close friends' credit cards; wait until spring and drive across the country to seattle, down the coast with stops in sf and la, hit austin, tx, new orleans, see a friend in tampa, friends in nc, and then up the east coast to maine, heading back to chicago through canada to visit a friend in toronto. while on said trip, the rest of the lottery winnings would be in the bank earning pennies -- woo hoo!

jm / January 5, 2011 9:22 PM

Invest wisely, for that will be my income - create my own pension and health plans. And write the will with care.
Buy a 3-flat so my kids and I would always have a home in my neighborhood and a place to come back to. And buy a nice cabin way up north to spend summers.
Set'em up for college - if that's what they want.
Fix up my mom's house and get her a new car. And pay any vet bills for her cats.
Make sure my siblings and their kids are covered.
Give some to extended family and a few close friends.
Get my teeth fixed and maybe buy some rare records I've never been able to afford. Travel? OK. Few times a year. Hostels and inns will still do quite fine [will have to come out of the pension income, though].
That covers what....one to two percent of it [maybe four to eight percent of the after-tax amount?]
Then give the rest away like the Gates Foundation, making it a full-time job. Who really needs that much anyway?! Nothing wrong in my life that a quick $3 to 5 million couldn't fix - for good. And the rest can do even more for others if carefully managed. Karma means a lot.

But I didn't win. Dang. Maybe next time.

kelly / January 5, 2011 9:46 PM

Pay off all student loans. Pay off my parent's medical bills. Buy my boyfriend a Mustang. Set up trusts for my niece and nephew's college education. After that, I like the idea of getting a house to rehab, and making that my home. Also would donate a fair amount to make recycling in Chicago easier. Then I would go to school full time for my nurse practitioner degree, as opposed to working while doing it.

paul / January 6, 2011 3:04 AM

I'd blow it all in a weekend.

James / January 6, 2011 9:26 AM

I used to say that I would keep the job. Scratch that, I'm putting in my two weeks notice and taking the day off to have a nice breakfast at Toast. I'll spend the morning finding the right attorney. I'll treat my lady to duck fat fries at Hot Doug's (on a weekday, cause that's how I roll now). Then, I'll spend the afternoon finding a trustworthy financial consultant. Gotta be smart about this whole thing.

I'll sign up for an extra guitar class or two at Old Towne School of Folk Music. Then I'll follow sheconsultant's lead and fly to Spain for intensive Spanish language classes. Knowing how to play flamenco guitar (thakns OTSFM) will help me fit in better with the locals, so they forgive my Spanish lisp. They also will likely enjoy the parties I host, catered by Rick Bayless.

Once I've mastered Spanish and have grown tired of the monotany of the Spanish social scene, I will hire a team of programmers to develop a Powerball Lottery smartphone app that allows users to buy their lottery tickets directly from their mobile phones. My fortune will multiply and I'll be doing good with my money, facilitating the growth of the lottery while providing folks the opportunity to also win big. Like me.

flange / January 6, 2011 9:43 AM

park for an hour.

Spook / January 6, 2011 12:08 PM

I'd contract the best haberdasher in London to design an outlandish Steam Punk wardrobe( including hats, glasses and boots) that I'd wear atop the head of my Spinosaurus!

printdude / January 6, 2011 12:57 PM

I'd buy some kickass cars and have my friends participate in out Cannonball Run in teams of two.

vise77 / January 6, 2011 1:12 PM

Travel, pay off bills for family and sit on the rest. Mabye fund a new media startup. I would have to work in some way, perhaps by volunteer. Sitting around drinking beer all day would get old.

Spook: with all respect, your fantasy sounds like something a disturbed child would say. Based on your previous comments here, I suspect you really put stock in your rather sick fantasy.

Spook / January 6, 2011 2:38 PM

Dear Vice77,

On Gapers Block,
I've only been truly offended, just.. one... single...time.

Congratulations, sir!

But don't blame me cause you got no creativity, you and your "media start up" and "family travels" Yea boy, you'd better hope I don't get that $330m Mega Millions, cause I'd come to calling, fo sho!

But only you wouldn't know it until it was far too too late!

In fact, when you heard "The Spinosaurus Mash" blasting from my speakers, you'd be too stuck on your "Conventional Wisdom" to even suspect that your DOOM was at hand!!!

Only when you heard the terrible prehistoric roar "Rhhaaaaaaaoooowwwahhhhhh" would you( sitting at your breakfast table eating cereal) look up from the sports section (or the comics) of the Chicago (cause you're a Republican!) Tribune.

But by that time the roof of your house would already be gone! You'd look up, and there I'd be, fully steam punk outfitted and rocking a an English derby, sitting sixty feet up atop my Spinosaurus!!!

You'd try to make all natural and nice, by saying "Hey Spook, want some Trix????"

I'd pull out my megaphone, look down at you and say " No thank you Vice 77. Trix is for disturbed kids with rather sick fantasies. But would you mind if my best friend Spinosaurus has a tasty snack????? Unfortunately for you this would only be a rhetorical question, son.

I will not get into the bloody details of your demise, body parts on the ground lying, entrails flying, you crying,time buying,
and all that blood. But it will not be pretty! Ha ha ha!

Fred / January 6, 2011 4:25 PM

Buy lotto tickets.

Andy / January 6, 2011 4:36 PM

I'd go to the zoo and get a lion. You stick a remote control bomb up the lion's butt... push the button on the bomb and you and the lion die like one.

Anon / January 6, 2011 4:37 PM

Tell the director at this nonprofit where I work why I won't be donating any of it to this place--because he's an asshole.

Lawrence / January 6, 2011 4:44 PM

I'll tell you what I'd do, man: two chicks at the same time. I think if I were a millionaire I could hook that up.

Nuke LaLoosh / January 6, 2011 5:36 PM

I would recreate myself to become a worldly inventor.

First, I would hire 25 professors to act as a personal university: learn as many foreign languages as possible, travel all over the world to learn about art, science, and culture, and spend a few years trying to learn as much math, chemistry, physics, and computer programming as I could.

After spending a 5 or 10 years becoming a scientific and cultural expert, I'd spend the rest of my life as a modern-day Thomas Edison, trying to create new things of value in my own little Menlo Park, right here in Chicago.

If I had anything left over, I'd buy/build the house they used to film "The Ghost Writer." So long as we are fantasizing.

Mike / January 6, 2011 7:38 PM

Fred, you're not far from the truth. I worked a lottery machine in college at a liquor store in Maryland and we paid out cash winnings up to $2,000 for the smaller jackpot games. Most winners would take their cash and use some of it play at least an additional $100 in Pick-3 or 4s. They'd stuff the rest of the cash in their socks and walk off toward the bus stop. Endless cycle. High-jackpot Lotto was a different animal though actually ... it brought out a different crowd. We'd get a line of middle class suckers out the door and halfway down the block.

mike / January 6, 2011 10:21 PM

I'd give it to a handful of 18 year old kids and watch them do hilarious and destructive things for a few years.