The Cayman Island Entry on Jack Lew's Resume

Getty Images

Jacob Lew

This is awkward.

When Jack Lew was chief operating officer of Citigroup's Alternative Investments unit, the bank had over a hundred subsidiaries based in the Cayman Islands. And Lew's unit controlled at least one of them. Maybe more.

While Republican senators have pressed the nominee for Treasury secretary about a $56,000 personal investment in a Citigroup venture capital fund based in the Cayman Islands, the much more extensive ties of Citigroup to the Cayman Islands have largely gone overlooked. The Obama administration has been critical of these kinds of offshore subsidiaries, which legally allow companies to sidestep certain U.S. taxes. Odd, then, that its nominee for the top US financial overseer would come from those ranks.

A spokesman for the White House would not directly address Lew's leadership of a Citi unit that controlled Cayman Islands based subsidiaries, other than to point out he had nothing to do with their creation or location.

"During Mr. Lew's time at Citigroup, he served as chief operating officer for two different business units. He did not have any role in creating investment funds or deciding where they were located," said White House spokesman Eric Schultz.

Sen. Orin Hatch, the ranking Republican on the Senate Finance Committee, pointed out that President Barack Obama criticized his rival Mitt Romney for involvement with Cayman Island based subsidiaries.

"It's amazing that the president could attack Mitt Romney when his then-chief of staff and his Treasury secretary nominee had served as a senior executive at Citigroup that had subsidiaries based in the Caymans," Hatch said.

In testimony Wednesday, Lew denied any conflict. (Read More:Lew Denies Conflict of Interest)

How involved was Lew with Citi's Cayman Islands ventures? Hard to pinpoint.

A 2007 filing with the Securities and Exchange Commission lists 90 Citigroup subsidiaries based in the Cayman Islands. The next year's filing lists 114 Cayman Islands subsidiaries.

It is not clear from the filing how many of these Cayman Islands subsidiaries were part of the Alternative Investments unit, a financial advisory unit catering to high-net-worth individual investors and institutional investors with financial products that included venture capital funds, hedge funds and private equity funds.

A former employee of the unit, who spoke on the condition of anonymity, said that it is likely a "substantial amount" of these subsidiaries were run by the unit.

Lew worked at Citigroup from 2006 to 2008. In January 2008, he became the chief operating officer of the Citi Alternative Investments unit. Before joining that group, he was chief operating officer of Citi Global Wealth Management. Lew was also a member of the Citi Management Committee -- a board of senior managers from many businesses within the bank.

According to the notice sent out on Jan. 2, 2008, announcing Lew's move from wealth management to alternative investments, Lew was "responsible for operations, technology, human resources, legal, finance and our regional coordination."

A 2007 brochure described the Citi Alternative Investments unit as having "14 investment centers" that included venture capital, private equity funds and hedge funds.

One of the Cayman Islands subsidiaries is named "Alternative Investments MGR Ltd." Another is called "Citigroup Alternative Investments Structuring Facility Ltd." This raises the question of whether these were part of Citi Alternative Investments. It certainly would seem to be confusing for the company to have investment funds with names identical to operating units within the company that weren't part of that particular unit's operations.

Other subsidiaries have more obscure names, such as "Catalyzer B3 Private Equity Investment Limited Partnership," which again raises the question of whether these were companies that would have been part of Citi Alternative Investment's purview, since it handled private equity investments.

One of the Cayman Islands subsidiaries, Kingsbridge Limited, was a holding company for a satellite operator named Asia Broadcast Satellite. Kingsbridge was owned by Citigroup Venture Capital International Proprietary Investment Partnership L.P. and Citigroup Venture Capital International Co-Investment L.P. both of which were also Cayman Island subsidiaries. According to the 2007 brochure describing Citi Alternative Investments, Citigroup Venture Capital International was part of Citi Alternative Investments.

A representative for Citigroup confirmed that Citigroup Venture Capital International Proprietary Investment Partnership L.P. was a CAI entity. The representative would not provide greater detail on which subsidiaries would have been part of Lew's group.

In connection with the personal investment in the Cayman Islands venture capital fund, Republican Sen. Charles E. Grassley of Iowa accused Obama of hypocrisy for nominating Lew.

"President Obama has been almost obsessively critical of offshore investments," Grassley said (according to The New York Tmes). "He called Ugland House 'either the biggest building or the biggest tax scam on record.' That makes this Cayman Islands investment of his top official and now Treasury secretary nominee worthy of attention. The irony is thick. Members of the Finance Committee will question Mr. Lew about his foreign investments at the hearing."

Citi Alternative Investment was broken into two parts in 2009, when the company placed the retail-focused parts of the unit into Citi Holdings and renamed the institutional investor business Citi Capital Advisors.

For more on the U.S. Tresaury, see:

What's Lew's to Do at Treasury?

Lew Faces Grilling on Citi Bonus, Cayman Account

What Would You Call Tim Geithner's Book?

Geithner's Legacy: Contention Through Financial Storms

Follow me on Twitter @Carney