Retirement - Gangster Style

Club Games

Street Hustlers

The Country Club
Harry's Patio

Gin Rummy

Some board and card games have a gangster feel to them. The games themselves are pretty mild, but the movies have given them a shady reputation.

We expect, for example, to see Gin Rummy played at the country club by guys named Vinnie and Frankie. A check changed hands at the end, and the unspoken message was, "This better not bounce."

At the other end of the continuum, we imagine street hustlers with slicked back hair trying to coax us into a three-card monte wager.

Street Hustlers

It wasn't that long ago that New York City supported a thriving community of street hustlers. On Sixth Avenue near mid-town, they'd have a row of small tables with backgammon games ready to go.

These guys were great salesmen. They'd pull you into the pleasure of the game with an easy banter and their views on the "back game" and the edge from an "early break." If you weren't a good player (like me), they'd offer tips. After a couple of games, even if you lost, you felt like they were your long lost cousins.

Every visit to New York, I'd contribute a few dollars to the game hustlers and always felt it was a bargain. Their spirit, the hustle, the Brooklyn was beautiful.

With the exception of the chess hustlers in Washington Square, you don't see many game players in New York City anymore. It's too bad.


Bill said, "I saw myself as a pretty good chess player, so I figured the New York chess clubs would be easy pickings.

Two steps into the place and the offers started. The bearded guy rasped, 'You can have white.' The hundred year old guy with the inch thick goggles called, 'I'll spot you a knight.' They scared me. I tried not to whimper as I left. Ha!"

Any self-respecting player needs to maintain a connection to the street hustler part of the gangster universe. Once you know where the enclaves exist, trips to Chicago or New York can be seasoned with a few games of chess or backgammon. It adds an entirely fresh dimension to travel.

Underneath it all, there's nothing phony about a good street game hustler. They can't cheat at chess, or backgammon. They're just very good, and love the games. The gleam in their eye and easy wit creates a style that is hard to forget.

These street characters are so colorful, and the games so tense with concentration, that it seems like you're in the middle of Bogart movie.

The Country Club

Private clubs are everywhere. Ritzy country clubs are the most visible, but small clubs like the Elk's, or the Knights, or Rotary abound. Many have poker nights and maintain a well-furnished billiard room.

With its membership restrictions, the club can be safer than hanging out with the street hustlers. If you have private clubs in your area, they are worth checking out.

Remember, the goal is to get out of the house and meet interesting people. Be sociable. Don't try to win their lunch money on the second day. There will be plenty of time for that.

Harry's Patio

Often the best club is your own back yard.

All you need is a deck of cards, an umbrella, and a jug of lemonade. Ask the guy raking leaves next door if he ever played gin. Who knows, he might fancy himself a chess whiz.

You can also recruit from your other game meetings. Invite a couple of the more pleasant players from the chess club over for lunch and a game. You don't have to travel, and you get to make tuna fish.

Getting Serious

I'm a good sport and everything, and I do appreciate a good hustle, but I also like to win.

Here's where the beauty of Gangster Style gaming comes in. Once you start enjoying a game and are ready to get serious, you have a clear path to success.

First, since you're retired, you have the time for extended study. Improvements in chess, for example, are difficult for someone without extra study time.

Next, you have the skills collected over the span of a career. You know how to organize a project, how to develop and adjust a playing strategy, and how to design a study program. On top of that, you have the persistence to pull it off.

Lastly, compared to other things you've done, this is a lark. You don't really have a deadline. You can learn at your own pace and enjoy the characters and situations as they arise. None of these games are easy, so you have enough study to challenge yourself.

Involve your life partner and you'll find the Gangster Style weaving into your way of life.

Okay, I'm getting carried away. Back to the first point, learning to win. The following section lists steps to improve your game.

Gin Rummy

A few books offer excellent Gin Rummy advice.

  • Gin Rummy: How to Play and Win by Sam Fry. Dover, 1978. * A classic.
  • Gin Rummy at Its Best from Beginner to Expert by George Fraed. Smith & Daniel, 1992. * Excellent stories.

  • Computer programs provide game simulations, and they never get mustard on the cards.


    Backgammon plays like a child's dice game, but the underlying strategy takes a while to master. The following resources will lead you through the improvement process.

  • Backgammon For Winners, 3rd by Bill Robertie. Cardoza, 2002. * By one of the greatest players.
  • Improve Your Backgammon by Paul Lamford. Everyman Chess, 2003. * Understandable graphics.

  • Comments:

    Anne said, "I know a lot of women who play backgammon. I think we were attracted to the game because it was so much fun beating the idiot guys at the single bars."


    Chess masters have written hundreds of instruction books. Don't worry. Your typical opponent will have only looked at or two. Start with a single opening, let's say Ruy Lopez, and go from there.

  • Easy Guide to the Ruy Lopez by John Emms. Everyman Chess, 1999. * On the advanced side.
  • Open Ruy Lopez by Glen Flear. Everyman Chess, 2000.
    * Nice job with the black response.
  • Hypermodern Opening Repertoire For White by Eric Schiller. Cardoza, 1999. * Getting off the beaten path.

  • Comments:

    Ed said, "I played the middle school (high school) champion of Russia once. He hardly looked at the board and carried on a conversation with two other people. He slaughtered me. It was impressive."

    Sandy said, "I like the queen pawn openings better. They're played less, and the extra familiarity gives me the edge."

    Knowledge drives chess. If you know more than your opponent, you will win. Luck seldom comes into play.

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