As the author it is my prerogative to jump ahead and provide the reader with the nub of a thing without a boring story attached. I shall naturally tell stories of Monopolisto Man's various successes with Oscar's Grind, but here I shall simply take up the theme of how Oscar's Grind does not work.
Oscar's Grind operates as follows. You bet one unit and your objective is always to win a unit. After a loss, you play at the level you are at until you win. On a win, you bet two units and maintain that bet until you have added a unit to your wins or until you have won. If you are still down from your initial bet, you add another unit on a win. You bet at that level until you are a unit ahead for the sequence.
Here are several ways to win one unit in which case you start all over again.
ONE UNIT BET L L L W -2
TWO UNIT BET W You are even so you start over with a one unit bet
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ONE UNIT BET W you start over with a one unit bet.
*
ONE UNIT BET L L L L L W -4
TWO UNIT BET W -2
THREE UNIT BET L L W -5
FOUR UNIT BET L L L W -13
FIVE UNIT BET W -8
SIX UNIT BET W -2
THREE UNIT BET W +1
Needless to say Monopolisto Man would have been in the soup with any sustained losses at higher levels. He therefore established some limits to avoid massive wipe-outs.
He would play for twenty units a session. He would confine himself to blackjack and play the Ainslee version of Basic Strategy which enables a wider range when doubling bets. For example doubling on a total of ten rather than eleven. This was something of a superstition, but Monopolisto Man was well beyond the stage of card counting by this time. He recognized that such counting was possible but that the price in sheer nerves was more than was to his liking.
After his Boston practice he boarded a plane for Las Vegas and was soon ensconced at Sam's Town, heading south from downtown on Boulder Highway. Sam's Town at the time dealt double deck blackjack, which suited Monipolisto Man just fine.
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