When you gamble with your time, you may be placing a bet you can’t cover.

What a queer gamble our existence is. We decide to do A instead of B and then the two roads diverge utterly and may lead in the end to heaven and to hell. Only later one sees how much and how awfully the fates differ. Yet what were the reasons for the choice? They may have been forgotten. Did one know what one was choosing? Certainly not.

The political arena leaves one no alternative, one must either be a dunce or a rogue.

"He hesitated till the last moment, but finally dropped them in the box, saying, "I shall win!" — the cry of a gambler, the cry of the great general, the compulsive cry that has ruined more men than it has ever saved."

Failure to make a decision was in itself a decision — he

Gambling is only the resource of those who do not know what to do with themselves

In a 50-50 life or death crisis, choose death.

This wavering paradox is a pillar of the outlaw stance. A man who has blown all his options can't afford the luxury of changing his ways. He has to capitalize on whatever he has left, and he can't afford to admit-no matter how often he's reminded of it-that every day of his life takes him farther down a blind alley.

Sometimes, however, it is better to take risks and play the most capricious, unpredictable move.

To play by David’s rules you have to be desperate. You have to be so bad that you have no choice.

I used to be a heavy gambler. But now I just make mental bets. That's how I lost my mind.

Sometimes, circumstances raise impossible decisions.
-William Pickering

Politics is a desperate business.

Suffering is caused by decisions not made.