When reporters descended on the mayor of Toronto's house the day after reports he had been seen smoking crack, a man in a blue T-shirt and sunglasses was waiting by the road to intervene. Before long, he was standing between videographers and Mayor Rob Ford's SUV, ensuring Mr. Ford could drive away.

Hours later, in a meeting with colleagues, the same man dropped a bombshell on Mr. Ford's chief of staff, according to sources. He said, according to one source, that he received a tip that the cellphone video was connected to a violent crime – and that the drug dealers trying to sell the video for six figures may have shot someone to get it.

The man is Dave Price, the mayor's director of logistics – a 49-year-old newcomer to mayoral politics but a long-time friend of the family. A Globe and Mail investigation has revealed that Mr. Price was a partner in a hash-dealing enterprise in the 1980s headed by the mayor's brother, Councillor Doug Ford.

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Doug Ford has denied that he ever dealt drugs. Mr. Price did not respond to requests for comment.

The former financial adviser who arrived at City Hall last month was brought in at a time of crisis for the mayor, who has faced mounting allegations of substance abuse.

Despite scant political credentials, he has played a role in a drama that has engulfed city hall and brought Canada's largest city unfavourable international attention.

Although he appears to be a key member of the mayor's inner circle, Mr. Price and his job responsibilities remain a mystery to even the closest allies of the Fords.

"Don't know much about David Price. Just met him," Councillor Doug Holyday said this week. Mr. Holyday, who is also the deputy mayor, later told The Globe and Mail that he had heard Mr. Price was getting paid more than some long-serving staffers.

When asked about the hiring of Mr. Price in April, Doug Ford's answer to reporters was simple: "You can't teach loyalty."

Police detectives have been asking what Mr. Price knows about the alleged video of Rob Ford. On May 17, according to sources, Mr. Price had a conversation with the mayor's chief of staff, Mark Towhey, about it.

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According to one source, Mr. Price told Mr. Towhey of a theory that the video may have been related to a homicide and he mentioned an address in connection with the video's whereabouts.

"Is that a theory or do you know that," Mr. Towhey said, according to the source.

Mr. Price, according to the source, told Mr. Towhey the theory was credible.

Seasoned city-hall observers recalled Mr. Price has been part of the mayor's entourage for years, without actually having any official role – although he was Doug Ford's campaign manager in 2010.

His relationship to the mayor and his brother goes back decades, according to several individuals who spoke both on and off the record. "The whole gang hangs out: Dave Price, Rob Ford, Doug Ford," said Frank Imineo, who has known Mr. Price for more than 10 years but had a legal and personal falling out with him more recently. "They've been friends for the longest time. Since kids."

According to several former street dealers who spoke to The Globe as part of an 18-month investigation, Mr. Price sold hash during the 1980s in partnership with Doug Ford.

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A few days after going to work for the mayor last month, Mr. Price's wife of 20 years had him served with divorce papers. She alleged that his gambling debts put the couple into a deep financial hole, despite Mr. Price's yearly salary of $125,000 as a financial manager in Toronto.

According to legal records accessed by The Globe, Mr. Price considers himself a "perfectionist" and a doting father. The documents portray a glimpse into the background and private life of Mr. Price: His mother was a tennis champ in her youth. He grew up with two brothers in a Toronto suburb, where he liked sports and was an average student. He claimed he was "mildly rebellious" during his high-school days. While he admitted smoking marijuana in his teens and 20s, the documents say he attested that he has not touched illicit drugs in more than 20 years.

Mr. Price graduated from York University with a degree in economics and gravitated toward a career in finance.

According to his LinkedIn profile, Mr. Price spent at least 10 years at State Street Trust Company Canada, a large, global financial-services firm. In his most recent role there, he was a vice-president in business and product development, a job requiring him to pitch the company's services to potential clients.

"I found him very easy to deal with; very pleasant, very responsive," said Denisa Farrow, a financial consultant who dealt with him.

Mr. Price left State Street in September, 2011. He separated from his wife a year earlier, according to divorce proceedings that were filed in court this spring.

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In an affidavit later filed by Mr. Price's wife, she said he was unemployed for several months after leaving State Street. This period, she said, compounded the financial worries of an already "financially devastated" couple that had also recently spent $75,000 fighting – and losing – a legal action.

In divorce proceedings, she also alleged that Mr. Price had incurred gambling losses that racked up a line of credit on the couple's Halton Hills home. Mr. Price has not filed a defence.

In a description on Mr. Price's LinkedIn profile, which has been taken offline, he described his skills of persuasion. "My most relevant communication trait is my superb listening skills – a key attribute when selling to any sophisticated prospective buyer," he wrote.

These days, he certainly has the ear of the mayor. T'was ever thus, sources close to Rob Ford said.

"You'd turn around and there'd be Dave Price hanging around with one of the [Ford] brothers," said one source who worked for Mr. Ford and spoke on condition of anonymity. "Any time something went wrong, he wasn't far away."With reports from Elizabeth Church, Greg McArthur and

With reports from Elizabeth Church, Greg McArthur and Tim Kiladze

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Tim Kiladze