Bloomberg’s Offshore Millions

“It cleanses the unrelated business taint from the total return,” Harvey Dale, of the N.Y.U. School of Law, told The Observer. “You invest in the same thing through an offshore entity. You are making the same investment; you are just putting an intermediary entity in the middle. Instead of investing directly in the hedge fund, you invest in the foreign entity, which, in turn, invests in the hedge fund.”

“Is (using the loophole) allowable under the law? Yes,” said tax expert Dean Zerbe, a former staffer at the Senate Finance Committee. “Is it something that is a best practice, particularly by an elected official? I think they should look very hard when they are engaging in this kind of activity. What does it say to the average New Yorker?”

The foundation’s tax returns indicate that Mr. Rattner’s team migrated much of its money to large hedge funds with ostensible island charters, including several in the Caymans, two of which list an address at P.O. Box 309 of the Ugland House, a building that “houses” an estimated 12,000 to 18,000 foreign businesses.

“Now, that’s either the biggest building in the world or the biggest tax scam in the world,” said Senator Barack Obama during his campaign for president. “And I think we know which one it is.”

But tax havens—despite the protestations of the president, a slew of senators and at least one district attorney—remain legal. “I made a lot of effort to shut down that loophole,” former district attorney Robert Morgenthau told The Observer.

Mr. Morgenthau said he’d spoken generally about offshore loopholes to four U.S. secretaries of the Treasury, twice to the commissioner of the general revenue and, as it happens, to Mr. Bloomberg himself. The mayor seemed uninterested in the offshore issue, he said. “I’ve talked to the mayor about it, and the budget director,” Mr.

Morgenthau said. “We did get help from the State Division of Taxation and Finance. But nothing from the city.”

In spite of the flurry of investments, it appears that for years, Mr. Bloomberg’s foundation had no office, phones, staff, Web site or public brochures. In late 2007, the mayor wrote a second letter to the Conflicts of Interest Board, looking for another blessing: Some of his staffers at City Hall, he argued, were asking him, “unsolicited,” if they could help with his foundation. Saying that the foundation would “ultimately serve city goals,” the board approved. At least three of his staffers were even allowed to use government resources, like office space, phones and Internet service, for foundation work.

One of the staffers was Deputy Mayor Patricia Harris. Aside from Mr. Bloomberg, Ms. Harris was the sole officer listed on his foundation’s tax return. A longtime Bloomberg loyalist, Ms. Harris worked at Bloomberg LP before joining the mayor at City Hall. On foundation tax returns, Mr. Bloomberg and Ms. Harris each claimed to have spent .25 hours, or 15 minutes, per week on the charity—as it gave away tens of millions.

Last month, the mayor announced that Ms. Harris would take on even more duties at the foundation, although it is unclear if she will increase her time commitment.

The mayor’s press office referred all questions about the foundation to the organization’s press office, run by former mayoral aide James Anderson. “In order to avoid conflicts, the Mayor is neither involved in nor apprised of the specific investment decisions made on behalf of the foundation—and we are therefore not in a position to discuss them,” Mr. Anderson wrote in an email.

Yet Mr. Bloomberg does often discuss his charitable endeavors. “Other than Gates, nobody’s given away this amount of money,” he boasted to the New York Post’s editorial board earlier this month.

But the Bill and Melinda Gates Foundation provides a contrast in its investment style. While the Bloomberg Family Foundation is hardly alone in embracing the savings provided by the offshore loophole—according to a 2007 New York Times piece, large universities like Yale and Duke, along with charities like the Rockefeller Foundation, engaged in the practice—The Times also reported that the Gates Foundation did not invest in offshore hedge funds.

“When instructing the investment managers, Bill and Melinda also consider other issues beyond corporate profits, including the values that drive the foundation’s work,” explains the Gates Foundation’s Web site. “They have defined areas in which the endowment will not invest, such as companies whose profit model is centrally tied to corporate activity that they find egregious.”