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"Putting it all on the line" is a phrase that has its origins in gambling. When you're playing blackjack or shooting craps, you have to place your bet (the amount of money you're gambling) on a painted line on the table. If you're feeling lucky and are betting every last penny you have, you literally put it all (all your chips/money) on the line.
The phrase has come to mean "give it everything you've got" or "give it your all"; to take the ultimate risk.
Kevin’s putting it all on the line. 
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