Given his history, it's perhaps no surprise that Trump's presidency is now entwined in legal theater peopled by outsize characters, including a porn star, a Playboy model, hustling lawyers and a mystery celebrity.
Those staples of a tabloid tale thickened the plot in court Monday in New York in the first step of a legal battle with potentially grave consequences for Trump, following the stunning FBI raid last week on his personal attorney Michael Cohen.
Pink-suited adult film actress Stormy Daniels -- who arrived for the procedural hearing in a media scrum -- blasted Cohen outside court, claiming he put himself "above the law" for years and "openly referred to himself as Mr. Trump's fixer."
In another shocking development, Fox News host Sean Hannity was revealed in court as Cohen's mystery client, adding another overdose of intrigue to what is already a blockbuster story, although a source familiar with the situation said there was no formal attorney-client relationship between them. Hannity called from time to time and got input from Cohen on legal issues, the source said, for which he was not billed.
However, news that the President and his most vociferous media cheerleader share a lawyer -- who is now facing his own legal abyss -- sent a ripple of disbelief through the courtroom.
"It is the kind of stuff that, if it was in a script or a novel, it would get thrown out for being implausible," John Avlon, editor-in-chief of The Daily Beast, told CNN's Erin Burnett.
The identity of Cohen's other client did little to flush the scent of scandal. Sources told CNN last week that Cohen had facilitated a payment plan totaling $1.6 million last year to a former Playboy model who says she became pregnant by Elliott Broidy, a leading GOP fundraiser.
But the barely believable tabloid twists could not obscure building danger for Trump, which might explain his public fury over the raid: The Cohen case may mark a perilous moment of convergence between his scandalous previous life and his presidency.
That's partly because, were it not for a $130,000 payment Cohen made to Daniels to keep her quiet about an alleged affair with Trump, the Cohen raid and Monday's hearing may never have taken place.
It is not clear exactly where prosecutors from the hard-charging Southern District of New York are headed, but the payment could amount to a campaign finance violation.
Daniels' telegenic lawyer, Michael Avenatti, is an adept media manipulator -- playing the President at his own game, stoking newsy moments and leveraging the legal system to inject his client's case into the media bloodstream.
He described Cohen as "radioactive."
"The President trusted Mr. Cohen as his fixer for years, he trusted him with his innermost secrets, and I think that the chickens are about to come home to roost," Avenatti said outside court.
There's an irony to the law of the tabloid jungle by which Trump lived for years possibly coming back to bite him.
After all, the President used newspapers to turn himself into a larger-than-life New York figure, making sure that his ego, his skyscrapers, his loves and his journeys through Manhattan's nightlife filled gossip columns for decades. It paved the way to stardom in a top reality TV show that made him a nationwide figure and led him to the biggest prize: the White House.
Trump's biography is written in the ink of New York tabloids.
"Best Sex I've Ever Had," blared a typical 1990s headline in the New York Post, quoting Marla Maples, who later became Trump's second wife.
The New York Daily News loved tormenting the Donald, once dubbing him "Trumpty Dumpty," but in 1999 it foreshadowed his future, splashing: "The Donald Tells the World: I want to be the Prez."
In office, Trump has stuck with the method that orchestrated a generation of media coverage in New York on the basis that all publicity is good publicity, even if it has often jarred with the decorum expected of the presidency.
He's traded in the tabloid sensationalism of emotion, outrage, anger and dripped-out intrigue over coming decisions, and has peeled off stinging attacks on political rivals, acting as the ringmaster of his own news circus.
In fact, his near-daily, early-morning tweets with their block capital letters -- last month he slammed the Mueller probe as a "WITCH HUNT" -- serve the purpose that a front-page tabloid splash did in the last century.
So far, revelations over Trump's colorful past -- like the "Access Hollywood" tape, on which he boasted about groping women, or controversial comments unearthed from Howard Stern's radio show -- have not significantly damaged him. During the 2016 campaign, they helped cement an image of the Republican nominee as a scourge to political correctness, beloved by elite-hating voters of the forgotten heartland.
But the bridge to Trump's past represented by the FBI's swoop against Cohen could test the President's Teflon hide.
The raid on Cohen increasingly looks like a new legal front, separate from special counsel Robert Mueller's probe, that could be immune from any attempt by Trump to neuter the special counsel.
Prosecutors say they have been investigating Cohen for months for alleged criminal conduct in his personal business dealings. Since his primary client is Trump, that could be bad news for the President.
The FBI executed a search warrant seeking evidence of bank fraud, wire fraud and campaign finance violations, sources told CNN.
They are also seeking information about any payments allegedly made to hush up women who say they had affairs with Trump years ago.
It is not clear whether documents and communications seized by the FBI include any discussion between Trump and Cohen about the President's past legal entanglements, or whether there is any criminal case to answer.
But in a worrying development for Trump, Stephen Ryan, an attorney for Cohen, said Trump Organization materials had been taken away by the agents. That could potentially give prosecutors a window into Trump's past business dealings and the financial affairs of his family, since Cohen has long been a trusted fixer and emissary for the real estate billionaire turned politician.
CNN's Gloria Borger contributed to this article.