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Just when it seems as if Mayor Rob Ford's troubled mayoralty may be moving out of the shadows, darkness descends again. The arrest of his friend and some-time driver Alessandro Lisi in a police operation thickens the cloud that has been hanging over him since drug-video allegations broke in May.

The whole crazy business is embarrassing the city and eclipsing important matters. This week, Mr. Ford is leading a delegation to study how Austin, Tex., uses its live-music scene to boost economic growth, but he is certain to face questions about the mess back home. One Austin paper ran a story that refers to Mr. Ford's recent troubles with a headline that calls him a "controversial Canadian mayor," hardly the kind of publicity Toronto wants.

The Lisi arrest is the latest incident involving the mayor's associates, and it raises questions about the company he keeps. Until now, he has deflected all questions with "I've dealt with that," or "I don't talk about personnel matters." It will not do any more.

The reports have become too frequent and too troubling to brush off.

Consider what we have been told in media reports over the past four months. That an infamous photograph of the mayor that emerged with the alleged drug video was taken at a house occupied by a long-time friend of Mr. Ford, Fabio Basso, who has had brushes with the law.

That one of the men in that photo has been murdered and two others rounded up by police in a drugs-and-guns raid. That Mr. Ford tried to visit another friend who has been in trouble with the law, Bruno Bellissimo, at a Toronto jail. Sources told The Globe and Mail that police have interviewed members of the mayor's staff about people including Mr. Lisi, and attempts to retrieve the alleged drug video.

Now Mr. Lisi has been charged with drug offences. That makes three Ford friends – Mr. Basso, Mr. Bellissimo and Mr. Lisi – who have drawn the attention of police.

Although Mr. Lisi has a long record, the mayor would like us to believe that his friend is a "good guy" who is "straight and narrow." He says he is shocked and surprised. He brushed aside most reporters' questions on Wednesday, insisting: "I've answered the concerns."

Not even close.

If the mayor expects Torontonians to believe that his involvement with these dubious characters is entirely innocent, he is going to have to tell them more.

Has he visited Mr. Basso's house? Is he aware of Mr. Basso's criminal history? Does he know the men in the infamous photograph, and what was he doing with them at the time? (His lawyer, Dennis Morris, has said the mayor has his photo taken with all kinds of people.) Why did he try to visit Mr. Bellissimo in jail? Is he a frequent visitor to Mr. Lisi's house, as the media have reported? Why?

As for the reported video, he has said only: "I can't comment on a video that I have not seen or does not exist."

It is not assigning guilt by association to demand answers to these straightforward questions. Mr. Ford cannot afford personal connections that throw a shadow on the integrity of his office.

"The mayor is the leader of our civic government, and as leader of our civic government, he should not be associating with criminals or those who are associated with the drug trade," Councillor Denzil Minnan-Wong, a member of the mayor's executive committee but also a possible mayoral rival, told The Globe and Mail's Elizabeth Church. "It sends the worst possible message to residents of the City of Toronto who wish to live in a safe city and where the drug trade is a serious problem."

None of this is going away unless Mr. Ford gives a clearer accounting to the public of his actions, and his controversial friends.