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GULLIBLE’S TRAVELS: Monopoly for members only

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Satire written by Kellyanne Conway’s dog

TO: Club members planning to attend the annual Regatta Ball

As you know we usually include a scavenger hunt as part of the fun, and who doesn’t just adore ransacking Daddy’s library for that first edition of Dickens or an uncle’s desk for an old America Cup crew badge? But this silly old virus means we can’t sneak aboard the Fort Fickle ferry and steal a life jacket. (How were we to know it was going to sink weeks later and all those people would drown?)

So this year let’s try some different fun. The challenge is to buy a home from the most economically distressed family you can find for the most ridiculously low sum. We’re looking for a real tear-jerking story to take the cup.


  • Families must have lost all income because of the virus.

  • Include at least three children under 15 years old.

  • Bank foreclosures don’t count.

  • You can use an agent for the boring details, but you have to bang on the door yourself and offer a ruinous price, knowing they are out of options.

  • To keep it fun, you must go in the Monopoly millionaire costume of a top hat, tails and fake white mustache.

  • You must bring one member of the pathetic family back to the club with you to tell the awful tale.  Julio from the kitchen has offered to translate if needed.


  • Handicapped child in the home?

  • Will the family now have to live in a car?

  • Double points if they have no car to live in.

  • Double points if one of the parents is a veteran.

  • Triple points if someone has cancer AND no insurance.

  • No points if they simply have to move in with relatives.


Do your research.  Talk to your servants or landscapers to identify the most tear-jerking story among their social stratum. There will be plenty to choose from. Best you have a backup family in case the bank beats you to the door. Prepare your sales contract. Bring a wad of cash in case everyone thinks they are “too proud” to return to the club with you to tell their story. There’s a 5-minute limit. You may do some coaching on the way back to the club. I imagine some people in their situation might go on a bit. Try to get them to avoid thoughts-of-suicide chatter. It’s supposed to be a fun evening.


Regatta Day: All players meet in the Spinnaker Lounge in costume! (Optional points for a crab and lobster bisque at around 11 a.m.) Mirriam from the 10 Meter Gang will pop the bubbly cork. When the last glass is filled, it’s “bottoms up” and out the door.


You have to be back in the building by 8 p.m. The Youth Achievement Awards will be just wrapping up. Each of your new “friends” will tell the heart-wrenching tale and the judges will huddle while the staff clears the floor for the Fred and Ginger Dance Tribute Show.


In lieu of prize money (who needs more money these days?), a donation will be made in your name to the Launching Dock Signal Flag Fund.


In these “gotcha” times when people like to take things out of context, please don’t take any video or audio. Remember Mitt Romney’s 47% speech recorded by a sneaky waiter? We don’t need our bit of fun to become a social-media fodder. On the bright side, the way this country is going, this may become an annual event.

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