Blackjack's Strategy of Maximal Boldness

Allan Wilson's classic Casino Gamblers Guide contains one gem amongst a myriad of valuable pieces of advice. Wilson advises the roulette player who does not play with an advantage, and who insists on playing roulette in spite of the inexorable and unforgiving house edge, to bet all of the money he plans to bet at roulette during his lifetime on red or black. The idea is to minimize the effect of the house edge. This strategy is known as the optimal strategy for all gambling games where the player has a negative expectation.

The strategy makes a few assumptions. For example, the pleasure of gambling over an evening is not considered (some would argue the house edge is an acceptable price of an evening's entertainment if you bet conservatively). Also, it is assumed the gambler is trying to win some fixed sum of money. However, Wilson's strategy has stood up to most theoretical challenges over the years.

Steve Jacobs, the Godfather of rec.gambling.blackjack, the internet's first, and arguably best, discussion group, developed Wilson's idea with reference to the form of roulette played in Las Vegas. Jacobs observed that if the house edge on two wagers is the same, it is better for the negative expectation bettor trying to win a fixed sum to take the more risky option, in this case a single number with its 35-1 payoff over the even chances such as red or black with their 1-1 payoff. Jacobs observed that you should bet 1/35 of whatever you need to reach your win goal, which is superior to betting it all on the even chance provided there is no rule in force such as en prison or surrender, which reduces the house edge on the even chances.

In light of Jacobs' observation I had a thought...what about blackjack? I've never seen a strategy for the negative expectation player who wishes to win a fixed sum published in print. In fact, I don't believe such a study exists. An optimal strategy would be very valuable in tournaments or for qualifying for certain unusual types of bonuses cropping up in various online casinos.

Such a strategy defies intuition. You cannot simply bet everything on one hand. That would not allow you to fortify your wager for splits or double-downs, etc.

We could look at the Jacobs roulette strategy and, observing that an average blackjack bet is about 1.3 times the initial bet you place in circle due to double-downs, etc., divide our win goal by 1.3 and bet that amount of money. But this strategy is clearly sub-optimal when you take into consideration the fact that you can't double-down or split for fractional amounts. So I'm throwing this down to the readers-I expect I will get a lot of different solutions!