NEW YORK -- The summit in Singapore isn't exactly the "Thrilla in Manila," but it's close -- both in proximity and buildup. So who will walk away with the better deal?

While little is known of Kim Jong Un, in just seven years the 30-something dictator has done what his father and grandfather before him couldn't do: rapidly advanced North Korea's nuclear program. And now, the ultimate feat: a meeting with the president of the United States.

President Trump has already made a prediction: "I think within the first minute, I'll know," he said. "Just, my touch, my feel -- that's what I do."

The summit -- reportedly a one-on-one meeting -- is exactly where Mr. Trump feels most comfortable.

Gwenda Blair, author of "The Trumps: Three Generations of Builders and a President," says a desire to win was ingrained into him from an early age.

He's been doing it since the 1980s. He painted a self-portrait in the "Art of the Deal," which led to a turn as a TV celebrity and ultimately a ticket to the White House.

But the self-proclaimed "deal maker in chief" has so far proven to be more of a deal breaker.

Tearing up international deals -- the Trans-Pacific Partnership, the Paris climate accord and the Iran deal. He's come up short on domestic policies like immigration and health care reform. Tax reform with Republicans in charge is his only big win so far.

Blair says Mr. Trump is now looking for a diplomatic knock out.

"I think the world cameras will be focused on the hand shake," Blair said. "You know, who can leave the biggest imprint on the others hand."

While millions of people will be watching for a photo op, billions of lives have a stake in the outcome. This is where the substance and details of any deal, arguably Mr. Trump's most important yet, play a crucial role.