Frequent reminders of his 2016 election victory -- and Hilary Clinton's loss -- are a long-running thread stitched in to many of his speeches.
The winners and losers motif is marvelous for his base, requires little explanation and fits his cursory rhetoric. Yet every time he deploys it, he erodes his and America's global standing.
His current conundrum with Saudi Arabia's Crown Prince, Mohammed Bin Salman, is no exception.
The Crown Prince -- the kingdom's de facto ruler -- has yet to explain how a Washington Post journalist and vocal critic of Saudi Arabia disappeared while visiting the Saudi consulate in Istanbul more than two weeks ago.
Trump's go-to position after taking a call from the Saudi King Salman bin Abdulaziz Al Saud on Tuesday was to accept not only that the King and the Crown Prince have no involvement in what Turkish officials maintain was Khashoggi's brutal murder and dismemberment, but to push the idea that "rogue elements" were responsible for it. The King is the father of the Crown Prince.
In the increasingly autocratic kingdom, even the prospect of the ambitious Crown Prince blaming underlings for an operation that required 15 men to fly from Riyadh to Istanbul, according to Turkish investigators, beggars belief.
But Trump chose not merely to buy it, but endorse and propagate it, too.
A little later, after a barrage of criticism and having dispatched his secretary of state to Riyadh to impress upon the King and his son how much their accounting means to Trump and America, Trump seemed to waver.
He said: "I just don't know. I'm going to have to see what they say ... Nobody knows if it's an official report. So far it's just the rumor of a report coming out."
Trump's instinct with the Saudis is reminiscent of his dealings with other autocrats. Think of Russian President Vladimir Putin and North Korean leader Kim Jong Un.
How many times have we heard Trump say about Putin or Kim that maybe they'll get along, or maybe they won't? More often than not, it turns out they get along just fine.
It's become his standard dodge when criticized for cozying up to autocrats.
For a man who used to build and sell property for a living, it's a wonder he ever turned a profit.
As President in charge of the bank of American goodwill, he is extending credit where it is at risk of never being paid back in full -- never mind making a profit.
In the case of Saudi's young Crown Prince, he may lose his investment all together.
He seems to be going out on a limb, backing the Saudis so much that if they mess up he will pay a price too.
The well-oiled Saudi DC spin machine is in overdrive, sowing seeds of concern about Khashoggi, which don't stand up to scrutiny. They are also pumping out lines about Saudi Arabia's long and important relationship with the United States, which, while factually correct, conflates the kingdom with the Crown Prince.
The implication: Lose faith in the Crown Prince and lose all those benefits.
Both Trump and his Secretary of State Mike Pompeo have been repeating those lines in earnest over the past few days.
On Thursday, Pompeo told reporters: "I think it's important for us all to remember, too, we have a long, since 1932, a long strategic relationship with the Kingdom of Saudi Arabia. They continue to be an important counter-terrorism partner. They have custody of the two holy sites. They're an important strategic alliance of the United States. We need to be mindful of that as well."
In an interview with the Associated Press Thursday, Trump raised the emotional stake with an open appeal to his base of support. He said of the Saudi Arabia/Khashoggi situation: ""Here we go again with you know you're guilty until proven innocent. I don't like that. "
He added: "We just went through that with Justice Kavanaugh and he was innocent all the way as far as I'm concerned. So we have to find out what happened."
Trump seems to be circling his own wagons in defense of the Crown Prince, also known by his acronym MBS, in a way he can sell it to his base. But murkiness in this investigation created by Saudi intransigence and at times obfuscation defies a simple binary analysis.
The rogue operation or rendition gone wrong narrative, helped by the President and leaked by others, will struggle to stand up to scrutiny.
Turkey has been leaking just enough to keep the issue in the headlines, judiciously serving up a soupçon of evidence at a time.
Imagine a scenario where Saudis offer their version of events and fire -- or worse -- a few top officials for dereliction of duty, even treason. And Trump, over the heads of senators and intelligence advisers, buys the narrative.
Imagine the same scenario a few days later, when Turkey drops another evidential bombshell. Not only is MBS burned, but so is Trump and big dollop of American credibility is spooned out of the pot and into the fire.
Trump's secretary of state says he impressed upon the King and his son the importance of coming clean in Khashoggi's disappearance.
"We're going to give them the space to complete their investigations of this incident, and when they issue their reports, we'll form our judgment about thoroughness, depth, and the decisions they make about accountability connected to that."
But what if the response is shades of gray peppered with dark corners and doesn't fit Trump's black and white world?
What if it's like so many other global challenges that Trump tilts at for which there is no immediate quick headline grabbing solutions? Like North Korea, where, despite Trump's hyperbole at the Singapore summit with Kim this summer, there has been no confirmed nuclear disarmament by the Hermit Kingdom. In fact, some analysts believe that it might have increased its nuclear weapons systems.
But what if the Saudis produce an ambiguous explanation? What if common sense and US intelligence ultimately points toward containing the fallout from an ally gone rogue?
Trump is already giving us a curtain raiser on his intent, tilting toward a pass for his autocratic ally in the Middle East.
On Thursday, a few hours after Pompeo asked for Saudi investigators to be given a little more time to complete their investigation, Trump faced reporters. When asked if Khashoggi was dead, he told them "it certainly looks that way to me. It's very sad ... It certainly looks that way."
Asked about consequences for those involved, Trump vowed it would be "very severe ... It'll have to be very severe ... But we'll see what happens."
And there we have it. Trump's code for "I have already made up my mind."
He still has space to back out of full-throated support for MBS and even put sanctions on the kingdom. But right now, his relationship with one of the Middle East's most powerful autocrats could be Trump's biggest gamble yet.
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