I'd still say it's not the likelihood or the payoff which matters, it's the expected return. If the payoff is massive enough to overpower how unlikely it is for Georgia to win, then it's worth setting up. It's also worth setting up situations which pay off if Russia wins, and the higher likelihood of that outcome should make us accept situations with lower payoffs in that case.

I can think of a few reasons not to follow this strategy:

- If our uncertainty is too high, we might want to avoid the risk; e.g. even if Georgia wins, we might not get anything out of it.

- If the commitment is too high, e.g. a Martingale.

- If setting up one outcome puts another at risk; e.g. if we fund Georgia's war effort, such that Russia would retaliate if they win; or the other way around; or both!