Rudy Giuliani sent Trump business rival Leona Helmsley to prison for tax fraud

New York is America's largest city, but sometimes it feels like it keeps recycling the go-go '80s with a tiny cast of characters. On Thursday, New York prosecutors charged the Trump Organization and its longtime CFO, Allen Weisselberg, with 15 counts of tax-related felonies. They pleaded not guilty.

The alleged tax fraud scheme, as laid out by prosecutors, is actually pretty simple: the Trump Organization used company money to pay Weisselberg's rent, car lease, and other personal expenses, allowing him to avoid paying federal and local taxes, and kept track of the money in a secret ledger.

"As I was reading the indictment, the one thing I kept thinking was: 'My God, this is some street-level mobster bulls--t,'" one former New York prosecutor told The Independent. "Two sets of books? That's like 'How to Commit Tax Fraud 101' at crime college." University of Chicago law professor Daniel Hemel added, "This is Leona Helmsley-level stuff."

Subscribe to The Week

Escape your echo chamber. Get the facts behind the news, plus analysis from multiple perspectives.

SUBSCRIBE & SAVE

Sign up for The Week's Free Newsletters

From our morning news briefing to a weekly Good News Newsletter, get the best of The Week delivered directly to your inbox.

From our morning news briefing to a weekly Good News Newsletter, get the best of The Week delivered directly to your inbox.

Sign up

Helmsley, who died in 2007, was a greed-is-good tabloid-staple real estate magnate who served 19 months in prison after being convicted of tax fraud in 1989. She and her husband, Harry Helmsley, renovated their Greenwich, Connecticut, mansion with millions siphoned from their hotel and real estate empire, which included the Empire State Building, among other properties.

The prosecutor who sent Helmsley to jail was Rudy Giuliani, then the crusading U.S. Attorney for the Southern District of New York. When Helmsley appealed her conviction, her lawyer was Alan Dershowitz. And Donald Trump himself kicked Helmsley when she was down, leaking a letter to the New York Post in 1988 amid an easement dispute over an Atlantic City property Trump bought from Penthouse magazine.

Howard Kurtz, now a Fox News media critic, contemporaneously described Trump's "deliciously vitriolic letter" to Helmsley in The Washington Post, saying it revealed Trump's "previously hidden capacity for venom." In the letter, Trump called Helmsley "a disgrace to the industry and a disgrace to humanity in general," and told her that without her husband, she "would not be able to randomly fire and abuse people in order to make yourself happy."

What Helmsley was convicted of and Trump's company indicted for is "the kind of crime that super-rich people think they can get away with — and that they can get caught for, particularly if they are brazen about it," Rachel Maddow said on MSNBC Thursday night. And "comically high-profile people" aren't exempt.