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As the Senate gears up to vote on the next Treasury secretary, President Obama's choice for the job, Jacob Lew, has been forced to navigate through something of a political minefield: As White House chief of staff and a former budget director, Mr. Lew has sought to show he has enough Wall Street experience to handle turbulent financial markets, but not enough to prevent him from reining in the powerful banking industry.

Mr. Lew, who is expected to win an initial nod from the Senate Finance Committee on Tuesday and sail on to approval in a full Senate vote, has battled a range of criticism, including questions about his lucrative tenure at Citigroup, a Cayman Islands investment, and housing assistance he received as an administrator at New York University more than a decade ago. To shore up his support, Mr. Lew has met privately in recent weeks with 41 senators and responded to 738 questions for the record. On Tuesday, he is scheduled to head to Capitol Hill for another meeting.

Much of the vitriol surrounding Mr. Lew's nomination concerns the terms of his employment at Citigroup, which seemed to reward him for leaving the bank if he took a high-ranking position in government. During Mr. Lew's confirmation hearing, Senator Orrin Hatch, a Republican from Utah, peppered him with questions about the terms of that contract, specifically challenging whether the contract violated the president's efforts to "close the revolving door."

Under his contract with Citi, Mr. Lew kept certain bonus compensation if he left the bank for a "high level position with the United States government or regulatory body," but not a competitor in the private sector, according to several people with direct knowledge of the contract.

Many of the most exacting questions have come from Senator Charles Grassley, Republican of Iowa, related to a money-losing investment in a fund based in the Cayman Islands. Mr. Lew had a $56,000 investment in the Citigroup fund, prompting questions from Republican senators about whether the investment was stashed there to dodge taxes.

At one point in the hearings, Senator Pat Roberts, Republican of Kansas, held up a huge picture of Ugland House, an office building in the Cayman Islands where thousands of companies, including Mr. Lew's fund, have registered. The display struck a particularly discordant note because Mr. Obama used the Ugland House as a symbol for tax havens in his first campaign for president.

"There's a certain hypocrisy in what the president says about other taxpayers, and your appointment," Mr. Grassley said at the hearing. Mr. Lew responded by saying that he had not received any tax advantages because of the investment's location and ultimately sold it for a loss.

Senator Grassley also pressed Mr. Lew for more details on hundreds of thousands of dollars in loans that New York University provided while he was an executive with the school.

"N.Y.U. provided the financing over a decade ago," Mr. Lew wrote in a response to Senator Grassley's follow-up questions, providing details on the dollar figures and construction of the financing. "During the intervening time period, I repaid the university and privately refinanced the mortgage on my home multiple times. I am still living in the same home today.

Mr. Grassley was not satisfied with Mr. Lew's written responses, saying he still had concerns about the transparency of Mr. Lew's compensation. "Mr. Lew has a lack of knowledge or a poor memory of some of the perks he received through his tenure at New York University and Citigroup," the senator said in a statement. "Most people who receive a $1.4 million loan from their employer remember the terms."

Much of the battle over Mr. Lew's income and former status on Wall Street is inconsistent, the aides contended, pointing out that Republicans broadly backed Henry Paulson, who left his perch as chief executive of Goldman Sachs to become Treasury secretary in 2006.

Despite the criticism, some Republican senators on the committee have signaled their support for Mr. Lew. In a promising sign for Mr. Lew's prospects, Richard Shelby of Alabama, who sits on the Appropriations Committee as well as the Banking Committee, said he would back Mr. Lew.

Mr. Lew is a longtime Democratic budget expert who has spent most of the past 30 years as a Congressional aide or in the White House working on issues like Social Security, taxes and fiscal policy. While still in grade school, Mr. Lew served as a foot soldier in Eugene McCarthy's presidential campaign. He later served as an aide to Tip O'Neill, the longtime speaker of the House. 

Mr. Lew quickly rose to more prominent positions, eventually serving as the powerful White House budget director, first for President Bill Clinton and later for President Obama.

President Obama chose him in no small part for that expertise. The next Treasury secretary will need to deal with the so-called "sequestration," a round of $85 billion in budget cuts to be made before the end of the fiscal year in September, as well as a fight over financing the government.

Mr. Lew began his relatively brief immersion on Wall Street when he joined Citigroup in 2006 as chief operating officer of the bank's global wealth management unit. But the role he took on in January 2008 as chief operating officer for the bank's Alternative Investment Unit stirred the most Congressional ire.

With some of the most volatile investments at the bank, the unit plowed money into hedge funds and private equity investments. Those investments helped to catalyze Citigroup's huge losses in the depths of the financial crisis, ultimately forcing the bank to take billions of dollars in taxpayer money.

In response to questions about the unit's investments, Mr. Lew told lawmakers that he was more of a logistics man, overseeing the budget operations, rather than hashing out investment decisions. Mr. Lew has struck this neutral tone before. In 2010 confirmation hearings for budget director, Mr. Lew described himself "as a manager, not as an investment adviser."

At one point, though, Mr. Hatch questioned whether Mr. Lew saw e-mails about the sort of souring complex investments that ultimately brought Citigroup to near collapse. Also at issue for Mr. Hatch was whether Mr. Lew knew that the unit bet against some of the financial products it assembled. "Did you not know about the marketing of the sales products in the unit you managed, in which case I wonder what you did do," Mr. Hatch said.

Mr. Lew has maintained that he was not involved in those decisions. "Yes, I was aware that there were funds that were in trouble," he testified, adding, "I didn't have responsibility for the funds themselves, but I was aware that those difficulties were going on."

The criticism of Mr. Lew reached a high pitch when Mr. Grassley questioned whether Mr. Lew thought it was morally sound to take a $940,000 bonus in 2008, just a day before the bank took taxpayer money to help avert its demise. Mr. Lew said simply that he was "compensated in a manner consistent with other people."