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It will *never* be guaranteed.
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Maybe that's too strong of a word. But facing the odds is a better bet. It's the same reason why you don't double down with a soft 17 against a face but you do every time when showing a 3.
You are always in the mix until the dealer shows the cards. But the smart man knows when to put it in his favor. And while it may not look like it, Cuban set the Mavs up in his favor for the forseeable future. And the Mavs have no future if he re-signs Chandler. And they definitely don't have a ring too.