What to do when Powerball jackpot reaches 1.3 billion dollars

Since graduating college in 1997, I have been an intern at 20/20, a production assistant at ABC News, an NFL writer for Maxim Magazine’s website, a bartender, a casino dealer, an aspiring screenwriter and now an enthusiastic writer and begrudging publisher of indie comics. The only thing I’ve done consistently in that time is play the lottery.

Am I good at it? Do I run kickstarters to pay for printing my comics? If you know the answer to the second question, you’ll know the answer to the first.

But I kid. I am actually great at the lottery. I’ve never won anything big and am EASILY thousands of dollars down through my lifetime, but I’ve learned how to get my money’s worth from what is essentially a voluntary tax. With the Powerball Jackpot STARTING at 1.3 billion dollars, I figure now is the time to tell people my “Strategies to Winning the Lottery Even When you Lose.”

Warning: Lottos are gambling, and gambling can become addictive. I don’t want anyone following the below advice who is a recovering gambling addict. Even a jackpot this big isn’t worth that price.


Wait!!! Do not spend the ACTUAL money before the drawing. Read my entire piece before you bankrupt yourself.

What I mean is, spend it in your head. Buying a lottery ticket is purchasing freedom to daydream. Today is Monday, if you get your ticket(s) today (and you should get them today, more on this later) you have almost three full days to spend 1.3 billion dollars in your head.

I know what you’re thinking: You won’t get all 1.3 billion dollars, Kev. Stick with me.

Daydreams are tax free. Unless you derive entertainment from tax law (and if you do, then own it, and tax the shit out of your imaginary winnings), then don’t worry about money going to Uncle Sam.

I “spend” the jackpot for every ticket I buy. Which means I get to spend the money differently every time.. Sometimes I’m the most generous, giving person in the world. Thinking about what I could do for my common man with money out of nowhere. Sometimes, other than family, all I want to do is disappear to a remote island with just me, the wife, kid and dogs, and a waterfall made of Margaritas.

This week my wife and I have decided that we’ll create a dog rescue catering to poodles, yorkies, bishons and Wheaton terriers. These four dogs are the types we can be around with our allergies, and since we want to be able to work the rescue, we’re keeping it nose friendly.

I’ve also decided that any indie comic friend I’ve made over the last few years will get a print run of one of their books that will allow them to really get their book out over the next few years without breaking the bank.

There’s more, but I don’t want to bore you with my daydreams, I want to encourage you to create your own.



Let’s be perfectly honest here. Buying a lottery ticket is an admission of a basic misunderstanding of math. The odds of winning are utterly incomprehensible. That’s why I still think I have a chance. I don’t comprehend the truth that I don’t.

But that failing on my part, can be seen as a blessing. I realize that a certain amount of entries into the contest scratches my itch to “have a chance.” One ticket doesn’t do it for me. It takes somewhere between $20 and $30 dollars a week to fool myself into thinking, I’ve got enough of a shot. But here’s the thing, I don’t have a desire to be mega, super, crazy rich. I’d be ecstatic to share a jackpot with others. Even if the ticket I buy this week wins, I’ll be happy even if there are multiple winners cutting into the actual jackpot.

Knowing this I find partners. The best team I ever worked with was a team of four. We all put in $10 a week and bought our tickets together. We never won, but I actually saved upwards of $15 dollars a week. Have $40 worth of entries comforted me that “I’d done what I could” and I let the chips fall where they fell. I don’t work with those friends any longer so I jumped into a pool with 6 families my child hangs around with.

Even if we don’t win (who’s kidding, I’m totally going to win), I will come out of this week spending less on tickets than I would have alone.

PS – If just one ticket allows you to participate in Tip #1, then just spend two dollars and have a blast!


I went shopping this morning. At 9:45 there were 6 people in line for tickets. That is the shortest lottery lines will be. Wednesday night, the lines will be 20 and 30 people long. With people buying 100’s of tickets at once.  Go get it today before the rush really starts.

Remember tip 1, it gives you more time to spend the money in your head.

I also recommend thinking outside of the box as the where you buy your tickets. Some bars have machines (Shout out to my UnderWars co writer and artist C.M. Brennan who can sell you the winning ticket at Big Dog Station in Oakland Park, Fl), some liquor stores (man I feel sorta debaucherous right about now), and out of the way bodegas. I’ve found that when the line is intolerable, a drive past the nearest Farm Store fixes everything in a jiffy.


Most people believe that if you do not take the lump sum, the lottery can take any unpaid sum away from your heirs when you die. Nope. Incorrect.

Here’s where the myth started. If you take the lump sum you are taxed the full amount immediately (along with an extra penalty). The entire amount is yours to play with as you see fit.

If you take the scheduled payout, you are only taxed yearly at whatever that yearly payout actually is.

So, you have a choice to get less in total now, or more in total over two decades.

This all sounds fair and good. BUT… people seem to think if you die your heirs are cut out of any remaining money owed from the scheduled payments. Nope.

If you die with scheduled payments pending, your heirs are taxed on the full amount pending. Meaning that if there is still $10,000,000 owed to you, they won’t see a check until the payouts cover the $4 to $5 million they would owe in taxes. They will still eventually get a payment, but will have to wait a few years before that happens.

This should not matter. If you win the lottery, you should immediately set up accounts with a financial adviser that take care of any and all beneficiaries before you spend a penny on yourself, anyway (ok, payoff your house and any credit card debt they could also inherit, but no Lamborghinis until the kid’s college is guaranteed) . So ok, they have to wait 6 years before the money comes in. The hundreds of thousands of dollars (or more) you’ve set aside for them should be enough for them to skimp by until the big payouts come. And if it’s not, do you really want to dump 80 mil in their laps they weren’t ready for?

I am not saying scheduled payouts are better than the lump sum. You make that choice for yourself, based on solid advice from business people who know what they’re talking about. But inevitably someone will tell you to take the lump sum because you can’t pass on the unpaid payments and those people are wrong.


You won’t win. I won’t win. But daydreaming about 1.3 billion dollars sure is fun. Think about it, you’d have to make a Star Wars film to make that kind of money.

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