Nice People Can’t Win Monopoly

19 Jun

Image by Christopher Dombres. Click to check out his Flickr PhotoStream

I don’t know why I play Monopoly.  It is absolutely impossible to have a pleasant time. 

It isn’t even just that I never win.  Which I don’t.  It’s that no one has a good time.  Correction – the person who wins has a good time.  They have a ball.  They’re rolling in paper money, lording over their hotels and making everyone around them feel insignificant.  It’s everything we wish real life could be.

For a moment last night, I was that person.  I thought the tables had turned and that for once, I was actually going to win.  About ten rounds in to the game, I was the only person on the board with a Monopoly.  I had decided to prescribe to my brother’s age-old tactic: buy everything, cut breaks to no one.  Being mean is the key to winning – absolutely ruthlessness is necessary.  It was working really well, but I wasn’t having any fun.  Everyone was just galloping, driving, and thimble-ing around the board and paying me money along the way, but there was no joy in it.  My opponents’ faces drooped, hope sank, and the game had become dull.

So I decided to trade.

It’s almost never a good idea to trade.  Trading is what causes all the problems.  But I considered how many properties I owned, how few everyone else did, and the fact that I’d already landed on Free Parking (house rule: Free Parking = Cash Bonanza) three times.  So I made a little trade.  Just a little red-property-monopoly-for-me, yellow-property-monopoly-for-my-brother exchange.

It was the beginning of my epic downfall.

I ran around the board several times, relishing in the fact that I had given him a false sense of hope.  I had inspired a security in him that would be torn down once I lorded over him with my magenta and red monopolies.  

That wasn’t how it happened.

How it happened was that my brother mortgaged all his properties except the yellow ones and invested in hotels.  And every time I went around the board, I  landed on one and had to fork over a thousand dollars.  Every time he went around the board, he landed on Community Chest.  No amount of house and hotel building I did on my properties could equal the wrath I faced on Atlantic Avenue last night.  

I can’t stand it.  I don’t even know why I play.  We could have been playing Scrabble or cards – games that involve intellect and laughter.  But we played Monopoly – a game of treachery and sadness.  And the thing is – I could have won.  I could have just hung on to my one Monopoly and let the game play out as I bled my opponents dry.  But I decided to trade so that people could actually enjoy themselves.  I thought it might shake things up a little bit – let people have a smile.  Because I’m a nice person.  That’s right.  Nice people can’t win Monopoly because it’s impossible to suck someone dry so slowly that each round they have to mortgage another property or offer to give you their firstborn son.  Nice people will ease off, and nice people will inevitably lose.

There are lots of board games out there, folks.  

Don’t fall for Monopoly. 



19 Responses to “Nice People Can’t Win Monopoly”

  1. misswhiplash June 19, 2011 at 9:18 am #

    Dear Jackie
    You learned so much last night whilst playing Monopoly. You must be a really really nice person to be able to see that winning in not everything. What is everything is giving pleasure to other people..that is the winning game..
    Well done little flower! and a big hug (((( ))))


  2. Jules June 19, 2011 at 11:54 am #

    Huhuhu. The game of Monopoly. Key example of the differences between men and women; natural competitive drive. There will be NO mercy in Monopoly. *crooked grin* Now onto finding people to play with…


  3. thesinglecell June 19, 2011 at 4:31 pm #

    Donald Trump probably kicked ass in Monopoly. I can see him, eight years old, pouffy hair, just wiping up the board with his grandmother or something. Yeah. Gotta be a jerk to win.


    • Jackie June 20, 2011 at 9:14 pm #

      Oh man, you’re probably right. I need to be ruthless to come out on top. I’ll get myself a set of Jackie Towers.


  4. wordsweneversaid June 19, 2011 at 4:47 pm #

    Uno is WAY more fun – add some vodka shooters and a strip tease penalty option and no one will ever want to play Monopoly ever again (trust me on this one…)


    P.S.? Even Battleship can be fun with the above additions to the play. (just sayin)


    • Jackie June 20, 2011 at 9:14 pm #

      There seems to be a consensus between you and Paul that drinking make bad games better. Note taken 😉


  5. The_Observationalist_NYC June 19, 2011 at 6:34 pm #

    Saw the title of this post and already agreed with your post. I’ve never had a fun time playing Monopoly; between that game and RISK, I can’t imagine a more sad, more frustrating board game.

    There has to be some sort of sociological experiment behind those games. They really do tell you loads of unwanted info about your playmates.


    • Jackie June 20, 2011 at 9:13 pm #

      Oh man – Risk has made even more enemies from friends than I can count. It is incredible, the ass whooping that’s necessary for someone to win that game. It’s an absolutely tragic display. So very right.


  6. Joanna June 19, 2011 at 8:05 pm #

    Hi there,

    I’m no monopoly expert but I’m 99.83% sure that it’s against the rules to mortgage properties when you have any houses or hotels. AKA all you cards need to be face up or no house for you. Sooooo by this I have deduced that your brother cheated making you the clear monolopy winner.



    • Jackie June 20, 2011 at 9:12 pm #

      You know? I LOOKED AT THE RULES FOR THAT. I couldn’t find it. I don’t know if I wasn’t looking in the right section or what the deal was, but I was pretty convinced that was some downright tomfoolery. DANG NABBIT.


  7. pegoleg June 19, 2011 at 9:01 pm #

    Haven’t you ever heard: nice guys finish last?

    I played Boggle with my daughter last night. She wupped me senseless. Me, who taught her her first words, and how to read, and everything she knows so she could grow up to be this smart, aggressive businesswoman/shark. I’m so proud!


    • Jackie June 20, 2011 at 9:11 pm #

      The master has become the apprentice. Congrats on a fine display of child-rearing 🙂


  8. paulbeforeswine June 20, 2011 at 6:45 am #

    I totally agree. Monopoly is fun for the first handful of trips around the board. But once all the properties are snatched up, things just go downhill. And QUICK. Unless you’re playing “Drinkopoly”…


    • Jackie June 20, 2011 at 9:08 pm #

      I imagine that also features a fine downhill slope – it’s just more fun 😉


  9. kitchenmudge June 21, 2011 at 2:05 am #

    Monopoly was designed during the Depression to show how ruthless capitalism is, and still gives you a pretty good analogy. There is some skill to getting rich, yes, but a few good rolls in a row can give someone an insurmountable advantage as long as that player is ruthless.

    The only game more ruthless is Diplomacy. I was hooked on that many years ago. Being a complete jerk for a few hours, making and breaking alliances, is kind of a high.


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