Federal law requires billionaires such as Sheldon Adelson who want to leave fortunes to their children to pay estate or gift taxes of 40 percent on those assets. (Vincent Yu/AP)

Sheldon Adelson makes no secret of his disdain for the estate tax.

“How many times do you have to pay taxes on money?” the casino magnate asks, leaning on a blue cane on the cobblestones of Wall Street on a crisp October morning.

A gravel-voiced man whose accent recalls his blue-collar Boston roots, Adelson, 80, has just rung the bell at the New York Stock Exchange. Shares of his Las Vegas Sands Corp. are at a five-year high, making him one of the world’s richest men, worth more than $30 billion.

Federal law requires billionaires such as Adelson who want to leave fortunes to their children to pay estate or gift taxes of 40 percent on those assets. Adelson has blunted that bite by exploiting a loophole that Congress unintentionally created and that the Internal Revenue Service unsuccessfully challenged.

By shuffling his company stock in and out of more than 30 trusts, he has given his heirs at least $7.9 billion while legally avoiding about $2.8 billion in U.S. gift taxes since 2010, according to calculations based on data in Adelson’s filings with the Securities and Exchange Commission.

Hundreds of executives have used the technique, SEC filings show. These tax shelters may have cost the federal government more than $100 billion since 2000, says Richard Covey, the lawyer who pioneered the maneuver. That’s equivalent to about one-third of all estate and gift taxes the nation has collected since then.

The popularity of the shelter, known as the Walton grantor retained annuity trust, or GRAT, shows how easy it is for the wealthy to bypass estate and gift taxes. Even Covey says the practice, which involves rapidly churning assets into and out of trusts, makes a mockery of the tax code.

“You can certainly say we can’t let this keep going if we’re going to have a sound system,” he says with a shrug.

Covey’s technique is one of a handful that together make the estate tax system essentially voluntary, rendering it ineffective as a brake on soaring economic inequality, says Edward McCaffery, a law professor at the University of Southern California.

Since 2009, President Obama and some Democratic lawmakers have made fruitless proposals to narrow the GRAT loophole. Any discussion of tax shelters has been drowned out by the debate over whether to have an estate tax at all, McCaffery says.

‘Campaign donors’

“From the Republican side of the aisle, you’re committed to killing the thing,” he says, adding that Democrats don’t want to tackle an issue affecting a handful of people. “And that handful are all in the class of campaign donors.”

Mark Zuckerberg, chief executive of Facebook, and Lloyd Blankfein, chief executive of Goldman Sachs, are among the business leaders who have set up GRATs, SEC filings show.

JPMorgan Chase has a special unit dedicated to processing GRAT paperwork, says Joanne E. Johnson, a JPMorgan private-wealth banker. “I have a client who’s done 89 GRATs,” she says.

Goldman Sachs disclosed in a 2004 filing that 84 of the firm’s current and former partners used GRATs. Blankfein has transferred more than $50 million to family members with little or no gift tax due, according to calculations based on his SEC filings.

Charles Ergen, chairman of Dish Network, and fashion designer Ralph Lauren passed more than $300 million each, calculations from SEC filings show.

Blankfein, Ergen, Lauren and Zuckerberg declined to comment.

Congress enacted the estate tax in 1916 to apply to large fortunes at death. Eight years later, it added the related gift tax to cover transfers made before death. Both rates are currently 40 percent, and the first $5.25 million of an individual’s wealth is exempt; the amount is $10.50 million for couples.

For as long as such levies have been on the books, lawyers have been devising strategies to get around them.

Congress created the GRAT while trying to stop another tax-avoidance scheme that Covey developed. In 1984, Covey, a lawyer at Carter Ledyard & Milburn in New York, publicized an estate-tax shelter he’d invented called a grantor retained income trust, or GRIT.

Covey figured out how to make a large gift appear to be small. He would have a father, for example, put investments into a trust for his children, with instructions that the trust should pay any income back to the father. The value of that potential income would be subtracted from the father’s gift-tax bill.

Not ‘well thought out’

Then, the trust could invest in growth stocks that paid low dividends so that most of the returns still ended up going to his kids. Six years after Covey started promoting this technique, Congress termed it abusive and passed a law to stop it.

The 1990 legislation replaced the GRIT with the GRAT, a government-blessed alternative that allowed people to keep stakes in gifts to their children while forbidding the abuse Covey had devised.

Covey studied the law and found an even bigger loophole. “The change that was made to stop what they thought was the abuse made the matter worse,” he says.

Fredric Grundeman, who helped draft the bill while he was an attorney at the Treasury Department and is now retired, says the framers didn’t recognize the law’s potential for abuse.

“How do I say it?” Grundeman says. “When Congress enacts a law, it isn’t always well thought out.”

Covey, 84, a Missouri native and former Marine Corps basketball player who earned a law degree from Columbia Law School in 1955, uses the words “romantic” and “beautiful” to describe the most elegant tax maneuvers.

Covey recognized that a client could use the 1990 legislation to avoid gift taxes if he did something that would otherwise make no sense: Put money in a trust with instructions to return the entire amount to himself within two years. Because he doesn’t have to pay tax on a gift to himself, the trust incurs no gift tax. Covey calls the trust “zeroed out.”

Because the client isn’t paying any tax upfront, the transaction amounts to a can’t-lose bet with the IRS. If the trust’s investments make large enough gains, the excess goes to heirs tax-free. If not, the only costs are lawyer’s fees, typically $5,000 to $10,000, Covey says.

Three years after the new law took effect, Covey created a pair of $100 million zeroed-out GRATs for Audrey Walton, the former wife of the brother of Wal-Mart founder Sam Walton. The IRS, which had banned such GRATs through regulation, demanded taxes and took her to court.

In 2000, the U.S. Tax Court found in Walton’s favor, determining the 1990 law didn’t prohibit a “zeroed-out” GRAT. Covey had won a rare prize: an official seal of approval for a tax shelter.

Two years after Covey’s court victory, Adelson set up a GRAT called the Sheldon G. Adelson 2002 Two Year LVSI Annuity Trust, Adelson’s SEC filings show. By 2009, he was juggling chunks of his fortune in as many as 10 GRATs at a time, filings show.

Adelson once discussed his approach to inheritance taxes in a legal deposition.

“Listen, the law says you can avoid taxes but you can’t escape taxes,” Adelson testified as part of a 1997 lawsuit over an unrelated business dispute. “We just want to do what is right, but it is prudent and it’s wise to prepare your estate to save taxes.”

Political donations

The son of a cabdriver from Lithuania, Adelson started his first business at age 12, selling newspapers with the help of a $200 loan. He got rich in the 1980s as the owner of a company that organized computer trade shows. Later he bought the Sands Hotel and Casino in Las Vegas.

A globe-spanning casino and resort empire followed. He drew national attention in 2012 by donating more than $90 million to groups that supported Republican candidates, including Mitt Romney, the presidential nominee and an estate-tax opponent.

In November 2010, Adelson sat for an interview with a Bloomberg News reporter in Las Vegas Sands’ corporate boardroom, tucked inside the palatial Venetian resort. He spoke of the perks of being gambling’s richest man: His weekend home in Malibu, Calif.; the homes in Israel and the south of France; the six jets that ferry his family between them.

Adelson had recently rescued Las Vegas Sands from the brink of bankruptcy. His company’s stock, which lost more than 90 percent in 2008, had recovered almost half of its value. That was good news for his place on the list of the world’s richest people, a ranking that he follows closely.

“I don’t need to pat myself on the back to say, ‘Look at all the good things I did,’ ” he said. “But the success and the comeback that I’ve enjoyed, and the company’s enjoyed, have been extremely gratifying.”

The share gains were also good for Adelson’s tax shelters. That’s because after Sands stock plunged in 2008, Adelson plowed even more of his fortune into new GRATs, the SEC filings show. When the stock rebounded, those GRATs swelled in value.

A few days after the interview, he would pour $725 million from one of his GRATs into trusts for the benefit of his family. If he’d given the same amount to family members without using a GRAT, it would have resulted in a gift-tax bill of more than $250 million.

25 GRATs

In all, Adelson and his wife, Miriam, have created at least 25 GRATs. At least 14 of the 25 trusts were zeroed out, according to the calculations based on SEC filings. Those trusts transferred at least $7.9 billion to family members, an amount that would otherwise have incurred gift taxes of $2.8 billion.

Adelson has six living children, including two teenage sons. By early 2012, more than a third of Adelson’s stake in the Sands — worth more than $10 billion today — had passed through GRATs to trusts overseen by his wife for the benefit of his family.

The titles of some of those trusts start with the first letters of his children’s names. Later, more GRATs added an additional $3 billion to the heirs’ trusts.

Outside the stock exchange in October, Adelson declined to comment on GRATs. Later, he passed a message along through Ron Reese, his publicist.

“Mr. Adelson did tell me to tell you that he has no intention of ever dying,” Reese says. ‘So the estate-planning conversation is moot.’’

Since Covey’s triumph in the Walton case, lawyers have tweaked his technique to generate even more tax savings. One idea, used by former Aetna chief executive John W. Rowe, puts corporate stock options into a GRAT.

Another, championed by Goldman Sachs banker Stacy Eastland in presentations at estate-planning conferences, envisions a husband funding a GRAT with the proceeds of an options bet with his wife.

“It’s very common,” Rowe says, referring to the use of GRATs. “It’s become standard practice in estate planning.”

Charles Dolan, whose family controls the New York Knicks basketball team and who is chairman of Cablevision Systems, has repeatedly swapped Cablevision shares out of his GRATs and replaced them with IOUs, his SEC filings show.

The technique multiplies the potential tax savings, according to a 2008 report by analysts at AllianceBernstein Holding. Through a spokeswoman, Dolan declined to comment.

The GRAT loophole is unlikely to be plugged anytime soon. Obama has included a proposal to limit the GRAT technique in each of his annual budget plans but hasn’t pressed Congress to act on it, says Kenneth Kies, a Republican tax lobbyist.

Committees in the House and Senate are working on what they call comprehensive tax overhaul bills. Neither plans to address estate or gift taxes.

Covey suggests one reason for the lack of action: Wealthy donors to politicians, both Democratic and Republican, want to keep the loophole in place.

“I’ve done a lot for Democratic contributors,” he says with a smile.

No one knows for sure how much all of these GRATs cost the U.S. government.

Taxpayers don’t have to report how much each GRAT ultimately passes to heirs.

It’s as if Covey built an invisible highway bypass that carries some of the biggest fortunes past the tax man’s tollbooth. He marvels at the billions that flow along this route.

“It boggles the mind,” he says.

The full version of this Bloomberg Markets article appears in the magazine.