Richard Roeper Blog

Bet the House!



         I’ve just signed a deal with Chicago Review Press to write my eighth book. The tentative title is Bet the House: How I wagered $1,000 a day every day for a month on everything from poker to the lottery to a flip of a coin.

         Of course, by the time the book comes out, it might be called “Who Wants to be a Millionaire?”, “The Biggest Loser,” “Lost” or “Deal or No Deal?” Oh wait, those titles are taken.

         Chicago Review Press published my last two books: Sox and the City and Debunked! They’ve got a great team, and I’m thrilled to be working with them again.

         Here’s the premise. Each and every day for 30 consecutive days, I must risk at least $1,000 on some form of gambling. I’ll keep a running diary each day, with an updated bankroll.

         The rules:

         If I manage to double the bankroll at any point, the risk will be increased to at least $2,000 every day.

         At one point I will have to risk at least 25 percent of the bankroll on a single sporting event, poker tournament, roll of the dice or hand of blackjack.

         If I lose the entire amount before the 30 days have expired, I must replenish the bankroll with my own money.

         I must gamble for at least two hours every day. If I lose the minimum $1,000 before the time has run out, I’ll have to dip into the next day’s bankroll to keep going.

         If I win, a portion of the profits will go to charity.

         It doesn’t have to be a different form of gambling every day, but I’m going to try to come up with as many variations as possible. A partial list:





         Off-track betting

         A major poker tournament in Las Vegas

         A charity poker tournament

         Dog races in Kenosha

         Online poker

         The lottery

         March madness: NCAA pools

         Wagering through a web site that takes bets on entertainment shows such as “Dancing With the Stars.”

         Sports betting

         Prop bets


         If anyone can think of other forms of gambling I’ve missed, I’m open to suggestions. And if you know of any specific gambling event in the Chicago area within the next month, when I’ll be writing the book, please let me know.



20 Responses to “Bet the House!”

  1. Amanda from Michigan Says:

    Your money or the publisher’s?

    Is it legal to bet on politics? I know people do take wagers on such things.

  2. Dwight Says:

    Richard, Richard, Richard…

    The first step is admitting that you have a problem.

  3. Kevin Lampe Says:

    I heard of this new betting parlor in NYC : The New York Stock Exchange ask for Dow Jones at the door.

  4. Dwight Says:

    Working title contest:

    “Poker-tize Me.”

    “An Honest Day’s Wager.”

    “30 Days of Spite”

  5. Dwight Says:

    “Bookie Monster”

    “Lincoln Longshots”

    C’mon, creative people. We can do better than “Bet the house,” can’t we? Help a brothah out.

  6. Shawn Says:

    “Stake through my heart”

  7. Shawn Says:

    “Stake Through My Heart”

  8. Shawn Says:

    Jose Canseco already has dibs on “Juiced:”

  9. Molly Says:

    Pull-tabs! Though I’m guessing there won’t be any parish carnivals in the next month to make this kind of gambling come true…..

  10. Lynn Says:

    The electonic Bingo and American Idol pools!

  11. Chris Says:


  12. Amanda Says:

    Russian Roulette isn’t the answer you’re looking for, right?
    Thought so, how ’bout Harness racing? My granny is all crazy about it, but I bet that she wouldn’t give a damn if there wasn’t money involved.

  13. Jennifer Says:

    Does regular ol’ bingo count? Hanging out with some of the older folks (in the church basement?) and spending $1000 on bingo cards for the night? Fun times!

  14. sean callahan Says:

    A buddy of mine and me have a bet on the 7 day weather forcast…here how it goes…Skilling v. Stakes go up based on the futher day. For example….Skilling says it’s going to have a chance of rain above 50% tomarrow after 12 pm, amd says it’s before 12pm….I’ll give 2/1 on Skilling..or the opposite. We can sit, push or go all in at any time….BUT!! after the 7 days are up…..we start a new game….we settle the $ at the end of the month.

  15. grahams Says:

    Come on, you HAVE to play some street 3 card monte… 🙂

  16. mer v Says:

    Since it’s day one, if you’re not the superstitious type, write down a number of how much you think you may win (or lose) by the end of the thirty days.

    Board game: If you choose to play Battleship, make sure it’s the electronic version (can’t get away with switching coordinates with the electronic version).

    Lottery: you might be better off with the daily games and the lotteries rather than the scratch off tickets. Crumbs everywhere and a free ticket at the most for your winnings has been my experience. Such a letdown they are.

    Just some suggestions from a very amateur gambler…

  17. Bill Says:

    Jai Alai, get in a trip to Florida before the weather warms up here.

  18. pookie Says:

    Here’s a few you can add: Baccarat, Video Poker Machine, the stupid wheel at the entrace of most casinos which is the worst bet in the house, Bingo, and Keno.

  19. Fergus Says:

    What is the initial bankroll – is it that $30K (of the minimum $1K/day for 30 days)?

    I’m not clear how the 2-hrs/day “rule” works – buying a lottery ticket or placing a bet on a game only takes a moment; does the time until the results are known count? Would you have to flip a coin for two hours?

    Can’t think of many other forms, though I understand the Brits tend to lay odds on some strange things. Maybe you could take a flyer on cricket, or something even more bizarre there? Do those oddsmakers include things like movie box-office openings? PITY you’re starting *after* the Oscars – you would’ve broken the bank!

    Sportswise, the timing lets March Madness in, but you’ll miss the NFL draft (which might have some odds too?). There’s Vitali Klitschko defending his WBC heavyweight title Saturday. You could maybe use “sports betting” a few times, by devoting a day’s wagering to a specific sport; e.g., all NBA games one day, or betting only MLB games (after April 5th – tricky at the start of the season?). The NHL regular ends April 12th (then the playoff SEASON begins!) – there might be a bet available yet on which majority of teams gets in? The Masters falls into your time-frame – there must be some form of betting on golf?

    Maybe you can find someone willing to bet a few thou you can’t write a column *praising* Blagojevich & Paris Hilton…??

  20. Chuckmonster Says:

    Richard – not sure if you’ve read this one, but author Andres Martinez did a somewhat similar study entitled “24/7: Living It Up and Doubling Down.” He took $50k book advance and spent 30 days in Vegas living it up at 10 casinos. His $30k = $1.65M in total wagers through the course of the trip.

    Possible title for your book: “Roeper’s Thousands.” Can’t wait to see how it turns out.

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