For two decades Trudeau has managed to skip through life in a snappy suit and wide brim hat, the picture of preparation and fine grooming.
His Boy Scout demeanor and movie star looks have endeared him to infomercial audiences around the world and endowed him with a tidy fortune, $37 million of which a federal judge has said he swindled from gullible consumers.
So it is noteworthy that Thursday night Trudeau is claiming he arrived in Chicago from his Swiss retreat without his second passport, an unusually forgetful move that now prohibits him from surrendering that passport to United States authorities.
When Trudeau arrived at U.S. courthouse in Chicago Thursday, he knew that federal authorities wanted his passports to prevent him from fleeing the country and that a federal judge might actually put him in jail just to make sure he didn't take off.
For more than six years the Federal Trade Commission says Trudeau has ignored a court order to repay jilted consumers $37 million for false promises they say Trudeau made in his weight-loss book and fraudulent claims in his infomercials.
Fed up with Trudeau's claims that he is broke an unable to pay, two judges in Chicago are now threatening the infomercial king with a return to jail or a high bond on the new criminal contempt charge he faces for not reimbursing consumers.
Thursday in court, Judge Ronald Guzman ordered Trudeau to surrender the two passports he holds, his American passport, which he turned over, and an Italian passport that he recently obtained by virtue of being born from an Italian mother.
But Trudeau claims he left the Italian passport in his Swiss residence inside a biometric safe that requires Trudeau's fingerprint to open.
The fancy safe is just one of the trappings of Trudeau's life, with the diamonds he wears, the expensive cars he's been known to drive and the suburban Chicago chateau where he has lived and the carefree attitude he displayed leaving court.
Trudeau was not put in jail Thursday, but is due back in both federal courtrooms on Monday.