Uh... could someone help me with this weird prop bet?

[DavidC]

A good friend of mine, who's good at poker, but light on gambling theory, gave me this question, and I'm not sure how to answer it.

The original question was so god-damned funny that I had to repost it in full, but first let me explain the inside info that goes into it:

1) I want to go to Costa Rica in the near future.

2) I enjoy Strongbow (a fortified apple cider)

3) My friend has a theory that since superheros are always dressed in their undies (speedos worn outside of spandex), that you instantly become stronger if you strip down to your underwear. Particularly if they are either red or blue.

---

> You walk into a tent in Costa Rica because you see
> "Free Strongbow" posted on the outside, and a hottie
> beckons you from just inside. You also are wearing
> nothing but your undies, so you know you can handle
> any trouble if it's a trap.
>
> Well, you get inside and there is a roulette table.
> This really huge guy shows up from the shadows
> He says you MUST wager $5000 on the
> roulette table or he'll kick your ass. Not fearing
> him in the least, being in your undies, you flip him
> the bird and start moving towards the exit. But
> quick as a motherfucker, he strips down to his
> undies and they are nylon red. I kid you not.
> You've got your plain white briefs on and he's got
> nylon red undies and he's four times as big as you.
>
> So you wager $5000 on the roulette table and [censored],
> you lose. But you walked in with
> $100,000,000,000,000.00. You could double your
> wager over and over until you made your money back.
> Or you can just walk out.
>
> What's your move?


---

Now, here's what I told him basically:

1) It's the martingale betting system, and it's just as -EV as flat-betting.

2) The money play is to walk, no doubt there.

3) He can google it if he doesn't like my answer.

---

Now, he isn't contesting that the martingale system is -EV, but he thinks that since you started with a loss, you should do it now, hoping that variance will take you to profitability.

I tried to relate this to poker, saying that you sat at a poker table and lost 10bb, found out the guys are awesome, and that you're probably -0.75bb/100 here. I said that the money play was to walk.

I said Caro says, "You're always even."

I didn't say (but do now), that Sklansky left a table when he was -200 after seeing that the guys there were pretty damn good, with the quote, "Enjoy my $200."

So... I basically don't know how to convince this guy that "He's always even."

I guess I could relate it to the "loser's tilt" in NLHE, where they start making loose PFR's when they're losing, in an effort to get their cash back... I think he would understand that it would be a bad play for him to do that.

For some reason, he's fixated by the amount of -EV being very small (i.e. BJ or roulette, a coinflip with a small edge, etc.). That also doesn't make sense, but what can you do?

Any help is appreciated.

I think I've done everything I can for him, given the extent of my knowledge.