But now Trump faces mounting legal and political pressures approaching midterm elections that could make his problems worse. And Rahm Emanuel, the former top aide to President Barack Obama who is now Chicago's mayor, is publicly warning that the mercurial commander-in-chief may blow past the hesitation of national security advisors in search of a rally-around-the-flag political boost. He wants Congress to flash caution lights.
"We have a phrase in this country: the October surprise," Emanuel, Obama's first White House chief of staff, told me in an interview. "I think in this situation he is looking to do anything and will do anything.
"If you're going to take military action, lay out the case," added Emanuel, who previously advised President Bill Clinton and served in the House Democratic leadership. "The Senate should be asking serious questions now — not after the fact."
A White House spokesman, Hogan Gidley, declined to comment.
Emanuel spoke following a New York Times report signaling U.S. interest in military action in response to the political and economic meltdown that has led more than 2 million Venezuelans to flee their country. The report said Trump administration representatives had participated in meetings with Venezuelan rebels about overthrowing Maduro, that nation's authoritarian leader.
The administration ultimately declined to cooperate with the rebels. But it still hasn't ruled out U.S. intervention.
As a senior advisor in the Clinton White House, Emanuel has been on the receiving end of the same kind of suspicion he now directs at Trump. In 1998, Republicans wondered aloud whether Clinton ordered air strikes against Afghanistan, Sudan and Iraq to divert attention from his affair with Monica Lewinsky and subsequent impeachment. Emanuel insisted the circumstances are not comparable because Clinton's orders were vetted and endorsed by his national security team.
In August 2017, Trump told reporters he had a "military option" for dealing with Venezuela. The Associated Press subsequently reported that then-National Security Advisor H.R. McMaster and other aides argued against it on both practical and diplomatic grounds, noting the star-crossed history of U.S. intervention in Latin America.
But Trump has made harsh attacks on Latino immigrants and warnings of more of them flooding across America's Southern border a core political message. One of his Senate Republican allies, Marco Rubio of Florida, has publicly embraced the idea of a coup.
Asked about potential U.S. involvement in Venezuela last month, White House press secretary Sarah Huckabee Sanders replied, "We're going to keep all options on the table."
Foreign policy experts in both parties share Emanuel's skepticism. Military action would pose myriad challenges: ousting Maduro, restoring order under a new government, stanching the exodus of refugees, securing the flow of Venezuelan oil.
"There's a strong case for setting up humanitarian assistance aid across the borders, but not to intervene," said Kori Schake, a National Security Council aide to President George W. Bush.
"What could go wrong is not the appropriate question," added Jake Sullivan, an Obama State Department aide. "What could go right?"
But not all national security professionals dismiss the idea.
"I understand all the pitfalls of intervention, but I also understand the pitfalls of allowing this situation to unfold," said Richard Haass, president of the Council on Foreign Relations and another former Bush advisor. Given the extent of suffering in Venezuela, he said the White House and Congress should consider assisting, though not leading, an intervention.
Haass acknowledged that the president's inattention to policy and reputation for impulsivity brings "a bit of baggage" to the debate. But "just because it's Trump," he concluded, "it ought not to be ruled out."
Emanuel sees a lot of baggage. Trump has shrugged off advice of top aides on numerous national security issues, from Russia's attack on 2016 elections to relations with North Korea to the Iran nuclear deal. Bob Woodward's new book describes the Trump White House as suffering a "nervous breakdown."
That's why Emanuel, who recently announced he won't seek a third mayoral term next year, wants Congress to ensure any action Trump might take has a national security rather than political justification.
"He has crossed so many lines," Emanuel cautioned. "I've never seen anything constrain him before."