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The mayor’s office said the chief financial officer is responsible for policing the lottery director.

David Umansky, spokesman for the office of the chief financial officer, said Mr. Roogow’s wife was being treated for cancer last year and that the office felt it humane to “not press [Mr. Roogow] on these matters.”

Depending on how to characterize a bona fide D.C. resident, he still might be skirting the intent of the law.

In December, Mr. Roogow’s wife answered a midweek call to the lottery director at the couple’s Maryland residence, saying, “He isn’t home right now.” A couple of weeks later, Mr. Roogow answered the phone at his Ellicott City home and feebly explained that he was “visiting his wife,” after arguing that he had satisfied the requirements for D.C. residency, which include registering to vote and obtaining a D.C. driver’s license and tags.

Indeed, Mr. Roogow registered to vote in the District in December — a year after he was given six months to become a resident.

In the scheme of things, officials such as Chief Lanier can point to property ownership and her contribution to the city’s tax base — to say nothing of her exposure to issues that affect D.C. residents — to justify a second home in Maryland.

Even Mr. Baron, who registered to vote and moved into the city upon being appointed, can claim a measure of compliance with D.C. residency law, although he is not just a renter but one who has enabled Mr. Roogow to dress up his arrangement with an apartment lease.

But Mr. Roogow’s case appears less plausible, and his widespread influence as a lottery director irritates people like Ms. Drissel, particularly considering his failure to pay taxes in the District. “There are very few households with adjusted gross income over $100,000 paying D.C. taxes and a highly paid leader who by law should live here should not get away with paying no state income tax,” she said. “This is bad tax policy and bad policy in general.”