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Most of the time, the prominent men hovered in different orbits and different cities. Yet for years now, their lives have converged here on this resort island of white beaches and rippling sea.

There was William Hairston, a local builder whose wife is active in Republican circles here. There was Michael R. Hollis, an Atlanta lawyer, entrepreneur and presidential history buff who vacations here.

And there was President Bush’s housing secretary, Alphonso R. Jackson, who golfed and socialized here and led the federal agency that gave hundreds of thousands of dollars in business to friends and acquaintances, including Hairston and Hollis.

One such friend, an Atlanta developer, received a $127 million contract last year as part of joint venture to rebuild a New Orleans public housing project. That developer’s company has paid Jackson more than $250,000 in fees since Jackson joined the Bush administration in 2001, for work done before Jackson joined government, the developer’s lawyer said.

Jackson, who announced his resignation in March, leaves office on Friday as federal authorities continue to investigate whether he enriched himself and friends with lucrative contracts. The investigation has also laid bare the connections between Jackson, who was determined to expand opportunities for minority contractors, and the ambitious men who benefited from those opportunities.

It is the story of a small circle of black businessmen linked by a shared affinity for conservative politics and their financial interests in the revitalization of troubled public housing stock, and how those connections may have helped force the housing secretary from public life.

In 2003, the year before Jackson was named secretary, 14 percent — or $134 million — of the Department of Housing and Urban Development’s contracts went to black-owned firms, officials say. By 2007, black-owned businesses were receiving 25 percent of HUD’s contracts, or $195.6 million.

Jackson has proudly promoted such statistics, saying that “a good bottom line with small and minority businesses helps to build a stronger America.”

Indeed, some of Jackson’s supporters deride the scrutiny of his casual friendships as a racist effort to undermine a prominent black official and several respected black businessmen, noting that no one has been charged with a crime.

Rep. James E. Clyburn of South Carolina, the No. 3 Democrat in the House, said he believed the investigation was fueled by officials determined to derail Jackson’s efforts to expand affirmative action.

“Is there something wrong with trying to make sure African-Americans participate in the contracting program with the American government?” asked Clyburn, who vacations here regularly and knows Jackson, Hairston and Hollis.

But over time, concerns have grown — first among some housing officials and later among federal investigators — as it became clear that several men who interacted with and had business deals with Jackson became beneficiaries of his efforts to further integrate the contracting corps.