April 15th is here, which means it’s time for that classic American pastime: dodging one’s tax obligations. Loopholes and write-offs are one thing, but more than a few famous people have displayed an utter disregard for the IRS. Below, we look at three boldface tax evaders — and then do an accounting of what they could have bought on 1stdibs with the money they neglected to report on their 1040EZs.
Leona Helmsley
The “Queen of Mean” built her ruthless reputation first as a landlord, and then as the doyenne of a luxury hotel empire. Worth over $1 billion, Helmsley was tried in 1989 for myriad offenses, including tax fraud. A former housekeeper testified that when she said to Mrs. Helmsley, “You must pay a lot of taxes,” the Queen replied, “We don’t pay taxes. Only the little people pay taxes.” (For the record, she later denied this.) Convicted of filing false returns, she fittingly reported to prison on tax day in 1992 to serve a 19 month sentence for her crimes.
One of the things that the government looked askance at was Helmsley’s illegal billing of home remodels as business expenses. Among the items she tried to pass off as legitimate expenses: a silver clock, a mahogany card table and a custom-made $1 million dance floor. Live like Leona with these equally opulent simulacrums.
Obviously, nothing was too good for Helmsley’s dog Trouble, to whom she left a $12 million trust fund. No doubt the Maltese didn’t lap his Purina from an ordinary dog bowl — this majolica masterpiece would have been more fitting for the pampered pup.
Helmsley was famously a chain-smoker. This solid gold cigarette case may have been worthy of holding the queen’s smokes — or it would have doubled as a bludgeoning instrument for disobedient underlings.
Nicolas Cage
The Oscar-winning actor is a longtime collector of art, jewelry, exotic pets and cars — including a fleet of Rolls Royces and Lamborghinis. Cage also has a taste for real estate and, at one time, maintained an eclectic portfolio of properties that counted a haunted New Orleans mansion, a Bahamian island and a German castle among its ranks. At the height of his career, Cage was a Hollywood top earner; in 2009, the actor raked in over $40 million. Nonetheless, Cage’s catholic and prolific collecting tastes left him in the red — and in the late ‘00s, the IRS went after him for millions of dollars in unpaid taxes.
A huge fan of comic books, Cage was forced to sell a very rare Superman comic in 2011 to pay off his debts. Fortunately, the Man of Steel netted over $2 million in profit at auction. We suggest Cage double down on the superhero investment strategy and spend some of that Ghost Rider 2 money on this Warhol-signed screen print.
One of Cage’s splurges was a Tarbosaurus dinosaur skull, which he snapped up for a cool $276,000. Settling for this equally awesome fossilized sea creature at $25,820 might’ve been a smart move: Every $200k counts when you’re reduced to starring in Drive Angry.
The star of Wild at Heart reportedly spent around a quarter of a million dollars on exotic pets, like an octopus and two King cobras. Here are a couple more animal-inspired items for his menagerie.
Al Capone
Al Capone was the ruthless mob boss who ruled Prohibition-era Chicago with an iron fist and a loaded machine gun. During his reign, Capone actively courted press coverage of his ultra-violent tactics, going so far as to grant magazine interviews and appear in newsreels. Despite accumulating a gruesomely high body count (and nursing a serious cocaine addiction), Capone continuously evaded authorities and retained control over his bloody empire. But in 1931 FBI agents finally nabbed Capone on tax evasion charges, cleverly leveraging a 1927 law that required Americans to declare ALL income — even income derived illegally. All told, the capo owed Uncle Sam $215,000, or $3.3 million in today’s dollars.
Apparently, the hardened criminal had a soft spot for elephants — he collected figurines of the animal and considered them to be good luck charms. This antique bronze statuette could have joined the herd the mob boss kept on desk.
Capone, who masterminded the infamous St. Valentine’s Day Massacre, used to keep a pair of field glasses at hand to scan the headlines of the papers on the newsstand below his office building. With the money he withheld from the government (and saved on newspaper subscriptions), he surely could’ve afforded these.
Capone’s devout mother — no doubt worried about his unsafe working conditions — gave him several religious medals. These enamel and gold Saint Christopher cufflinks would have been a dapper upgrade for the don.
