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.

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.
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.
A free daily email with the biggest news stories of the day – and the best features from TheWeek.com
Peter has worked as a news and culture writer and editor at The Week since the site's launch in 2008. He covers politics, world affairs, religion and cultural currents. His journalism career began as a copy editor at a financial newswire and has included editorial positions at The New York Times Magazine, Facts on File, and Oregon State University.
-
9 grab-and-go toiletry sets that make packing a breeze
The Week Recommends All the essentials in one place
-
'Thriving' ecosystem found 30,000 feet undersea
Speed Read Researchers discovered communities of creatures living in frigid, pitch-black waters under high pressure
-
Harris rules out run for California governor
Speed Read The 2024 Democratic presidential nominee ended months of speculation about her plans for the contest
-
Harris rules out run for California governor
Speed Read The 2024 Democratic presidential nominee ended months of speculation about her plans for the contest
-
Trump sets new tariff rates as deadline nears
Speed Read New tariff rates for South Korea, Brazil and India announced
-
Ghislaine Maxwell: angling for a Trump pardon
Talking Point Convicted sex trafficker's testimony could shed new light on president's links to Jeffrey Epstein
-
Senate confirms Trump loyalist Bove to top court
Speed Read The president's former criminal defense lawyer was narrowly approved to earn a lifetime seat
-
Ghislaine Maxwell offers testimony for immunity
Speed Read The convicted sex trafficker offered to testify to Congress about her relationship with late boyfriend Jeffrey Epstein
-
Judge halts GOP defunding of Planned Parenthood
Speed Read The Trump administration can't withhold Medicaid funds from Planned Parenthood, said the ruling
-
Trump contradicts Israel, says 'starvation' in Gaza
Speed Read The president suggests Israel could be doing more to alleviate the suffering of Palestinians
-
The Pentagon's missing missiles
Feature The U.S. military is low on weapons. Can it restock before a major conflict breaks out?