A dude walks into a casino and then...

So, let's say I walk into the casino with $100 in my pocket. I am not going to leave the casino until I have either lost the full $100 or I have $500 in my pocket.

If I don't have either after 4 hours I'm going to go to the roulette table and put it all on 5.

What's the best game for me to play?

Depends. If you are a positive EV poker player or sports bettor, can play perfect video poker strategy at a 100%+ pay table, or accomplished blackjack card counter you should do one of those. Assuming that's not the case, you should play craps. Even though it's a low house edge, there are enough decisions per hour that you're sure to reach one of your goals.

This opinion is offered by weight, not by volume. Contents may have settled during shipping.

video poker if you have trained yourself to play. No matter what you play, you could be down to zero with-in minutes. I lost 400 in less than 20 minutes 15 bucks on, odds behind on craps.

So, I can definitely see how I could lose $100 very quickly playing blackjack or VP or craps. It seems highly unlikely, however, that I could get up to $500. All of those games are paying basically a dollar for every dollar bet.

If I'm betting even $10 per hand I would have to win 40 more hands than the house. That seems very unlikely on bets which are close to 50/50.

I think I need a game where the payouts are less often but bigger. Perhaps roulette is my game...

If I place 20 $5 bets there is better than a 50/50 chance that I hit at least one number. That would give me $175. Now I can place 15 $10 bets. That would give me about a 50/50 chance of hitting something again and would increase my stack to $375. If I make 20 more $10 bets and hit a third number I would have $525 which is enough to cover tips for the waitress and the dealer and still walk out with $500.

What's more likely, to hit three consecutive 50/50 propositions or to play hundreds of hands of blackjack or video poker and beat the house by a margin of 40 hands?

Hmmmm. Going back to high school math now, so this may not be right.

But I think you have a 1 in 8 chance of hitting three 50/50 propositions in a row. For any negative EV game (-5% for roulette, -1 or 2% for craps) the long run is your enemy.

So I guess you have to further specify your goal. Do you want any entertainment value? Is the expected results (busto or +$500) equally acceptable?

Given the sequence of bets you lay out you have worse then a 1 in 8 (12.5%) chance of winning the 3 bets in a row, it is actually 11%.

As to VP it will depend totally on the game you pick (positive or not), the denomination you play and your skill. $100 though isnt much of a bankroll regardless of the VP game.

For blackjack it depends on the house rules, number of decks and knowledge of basic strategy. If you bet all $100 on one hand, win and bet the total of $200 and if you win risk just another $100 you will need to win 3 hands in a row at blackjack. The odds are better for winning 3 blackjack hands in a row then your 3 roulette bets in a row.

I'm not a math whiz and don't know percentages but...

I like the Blackjack option - if you are playing a single deck, 3:2 table and happen to get lucky and hit a BJ then you've just upped your earning per hand. I'd bet $25 per hand - if you win put $50 out, win leave the $50, win and go $75.

Everyone knows it all depends on the deck. If you are heads up with the dealer and the cards are in your favor it could be an easy +400 or a quick exit if they are not. At least with BJ you have a little more control on the fate of your win/loss. Roullette is blind luck... Craps can go just as fast as you earn it.

You said you have 4 hours to play before going for the gusto - do it at a BJ table.

Just for fun I tried this on a practice game. Three times in a row I busted the $100 on the first spin. Not my idea of a good money maker. It doesn't sound like this is your thing, but I'd rather grind it out at a Black Jack Table, Craps, or even a Baccarat. One thing I've learned when trying to win big and fast (usually from chasing losses) you can't dig yourself out of a hole.

So, if I'm understanding this all correctly, you are giving yourself the choice of having either a 100% Loss Limit or a 400% Win Goal. With those options, I'd say that I think that you are much more likely to hit that kind of Loss Limit rather than that kind of Win Goal (a 400 Percent return).
Quadrupling your money is definitely a rough way to go -- giving yourself a very uphill battle to fight (and I certainly would not recommend that)!

But, if I were forced to do something to increase my likelihood of having more money (although I would have a much lower Win Goal than that), then I would do what I could do to do that by playing games with lower variances and higher returns.

So I think that this could be more likely done by playing Blackjack, Video Poker or Sports Betting. But, on top of that, it really would also depend on the rules and/or pay schedules that were being offered as well as on how versed you are in playing these games in the best possible manner.

RecVPPlayer

If I understand the question correctly, all he actually needs to do in the four hours is overcome the house edge on the #5 roulette bet.

He can't overcome that edge by giving the house an edge during that four hours. That is unless he can GET a bigger edge than he's giving, so the answer must be sportsbook or poker room. But both of those require considerable work outside the casino.