His friends agree that being mayor might not be his style. Sure, he has the instincts, experience, energy and grass-roots appeal necessary for the job, they say. But they also say he's too blunt, enjoys earning money too much and is too much of a free spirit to fit the strictures of being mayor.
"Dan is strictly his own man," says Westley B. Johnson, owner of the Five Mile House, a Reisterstown Road club that Mr. Henson has frequented for years. "He says things that people don't want to hear."
In fact, Mr. Henson was reluctant to become housing commissioner, partly because of the restrictions that come with a public position. Also, at 50, he did not like the idea of taking a pay cut.
"I was reaching a point in life where I was finally starting to make real money," he said, only half joking. As commissioner, he makes $106,000 a year.
Taking the job also required him to sell his share of Struever Bros., Eccles & Rouse Inc., the politically well-connected development firm where he was a vice president. He also relinquished control of the Henson Co., a consulting and development firm, to his two children who now own a 60 percent share; the remaining 40 percent is owned by the principals of the Struever firm.
The Henson Co. is working on a $300,000 contract to implement an affirmative action plan at the $161 million Christopher Columbus Center marine research center being built in the Inner Harbor.
Mr. Henson's business dealings sparked concern on the City Council that he would have too many conflicts to operate effectively as housing commissioner. But the head of the city's ethics commission signed off on his appointment. And Mr. Henson's friends scoff at the criticism, calling it naive.
"He gets all this grief because he is a businessman," said C. William Struever, a close friend and former business partner. "He's really making a sacrifice to do this. He is a guy who knows how to get things done."
Mr. Henson makes no secret of the fact that he enjoyed the money and freedom that came with being a private businessman. And he plans to return to it "in a couple years."
But while he sometimes pines for a life in private industry, he also saw compelling reasons to become housing commissioner. One was that he felt the housing agency was primed to move forward after years of budget cuts and regulatory hassles that plagued the agency under Republican administrations.
"The difference for me is Bill Clinton and [U.S. Secretary of Housing and Urban Development] Henry Cisneros," Mr. Henson said. "I would not have wanted to function as a budget cutter, as somebody who had to lay off people, as somebody who had to constantly look at ways to meet the same and even bigger challenges with fewer resources."
The other reason was political. He wanted to help the mayor shore up a part of his administration that was severely criticized under Mr. Hearn.
It is not the first time that Mr. Henson has come through for Mr. Schmoke, who grew into a friend and confidant after they met in the 1970s. For a while, the two worked in the Carter administration in Washington, talking business on the phone nearly every day.
They became closer when Mr. Schmoke was a federal prosecutor looking into loans and grants received from the federal Minority Business Development Agency, which Mr. Henson directed from 1979 to 1981. The investigations focused on loan recipients, not the agency.
The friendship was sealed when Mr. Schmoke was considering his first political campaign -- a run for city state's attorney in 1982. Mr. Henson was among the first people he went to for help.
"He looked me straight in the eye and said, 'I am interested in running for state's attorney and I need your help,' " Mr. Henson recalled. "I turned around and laughed at him."
Mr. Schmoke came to Mr. Henson because he had long experience in politics. "Since 1968, I can't think of a major campaign involving an African-American candidate that I was not involved in in some way, shape or form," Mr. Henson said.
Mr. Schmoke's campaign would be no different. Once the laughter subsided, Mr. Henson went to work despite his doubts about the candidate's chances. Of course, Mr. Schmoke went on to win the race, cementing their political relationship.
"He is good at the business side of politics," said Larry S. Gibson, the mayor's campaign chairman, to whom Mr. Schmoke went at Mr. Henson's suggestion. "He was our political secretary of state. He handled negotiations with other elected officials."
Those negotiations involved the currency of politics -- money and manpower to fuel and mobilize campaigns. As a result, Mr. Henson made enemies as well as friends. As a result, the mayor's political rivals feared that as housing commissioner he would punish the mayor's enemies and reward his friends. But there have been no complaints to date.
"So far, so good," said Councilman John L. Cain, D-1st, who had complained of political threats from Mr. Henson's camp.