Bruce Carson went bankrupt, with thousands of dollars of debt, before becoming one of Prime Minister Stephen Harper's closest advisers.
Documents obtained by The Canadian Press show Mr. Carson declared bankruptcy in 1993, then was hounded by creditors again in 2002 - shortly before going to work as then-opposition leader Harper's director of policy and research.
He declared a debt of $103,359 in the 1990s, and $369,000 nine years ago, the records show. No further information is given in the bankruptcy documents.
Mr. Carson - who is being investigated by the RCMP over allegations of illegal lobbying - said his 2002 money woes ended as a "commercial proposal," which lets a person or business pay back creditors, generally over an extended period.
"The second was not a bankruptcy but a proposal to creditors which I made and it was accepted," he said in an e-mail Wednesday. He would not comment further.
The Prime Minister's Office also declined comment.
Mr. Carson has a chequered past. He was disbarred by the Law Society of Upper Canada in 1981, and served time in jail after pleading guilty to two counts of defrauding clients.
Minutes from a July 16, 1981, meeting of the society's discipline committee shed light on why Carson was disbarred.
"He had forged the signature of the president of a corporation and misappropriated over $15,000 belonging to the corporation for which he acted," the document says.
"[He]forged the signature of a client from whom he misappropriated over $4,000; and misappropriated $4,900 belonging to another client."
Mr. Carson reinvented himself as a constitutional expert and became a political insider, working under Progressive Conservative prime ministers Joe Clark and Brian Mulroney, as well as Ontario Premier Mike Harris, before going to work for Harper when he became leader of the opposition.
Mr. Carson remained with Harper after the Conservatives won the 2006 election. Around political Ottawa, he was known as "the Mechanic" for his ability to fix tricky situations.
Senate Majority Leader Marjory LeBreton underscored Mr. Carson's worth to Mr. Harper's office during a November, 2006 Senate debate, calling him "a valued employee of the Prime Minister's Office."
Mr. Carson left the PMO in 2008 to head the Canada School of Energy and Environment, in Calgary.
He later accompanied then-environment minister Jim Prentice to an April, 2009 meeting with the U.S. energy secretary, and he was part of Canadian government's delegation at the Copenhagen climate summit that year.
But the 65-year-old Carson apparently yearned for his old life. Those who know him say he lobbied cabinet ministers last summer to use their influence with the prime minister to get him appointed as Harper's chief of staff. That job ultimately went to Bay Street executive Nigel Wright.
Mr. Carson worked at the Calgary-based think-tank until he took a leave of absence from the job last week.
That abrupt departure came after an investigation by the Aboriginal Peoples Television Network said Carson was allegedly lobbying Indian Affairs and the minister's office on behalf of an Ottawa-based water company that employed his girlfriend.
Michele McPherson, 22, stood to benefit from a plan to sell water-filtration systems to reserves with water-quality problems, APTN reported.
According to the network, McPherson signed a contract last Aug. 31 that would entitle her to 20 per cent of the project's gross sales in a venture Mr. Carson was pushing.
The company, H20 Global Group, released a statement Wednesday saying Mr. Carson never did any lobbying for the company.
"Mr. Bruce Carson has never lobbied for the company and has simply provided advice to assist us in understanding the process."
The company added it cancelled McPherson's 20-per-cent contract last month.
Mr. Carson has said little since the first APTN story aired.
Businessman Patrick Hill incorporated a business called H20 Water Professionals on July 14. McPherson joined the company last year. On Oct. 22, the company formed another entity called H2O Global Group to deal with Indian Affairs on the First Nations water project.
Property records show Mr. Carson and Ms. McPherson paid $389,500 in December for a house in Mountain, Ont., about an hour's drive south of Ottawa. APTN also reported that Ms. McPherson drives a black Mercedes SUV that Mr. Carson purchased.
The Prime Minister's Office has called in the RCMP over the allegations in the APTN reports. The matter was also referred to the office of the conflict of interest and ethics commissioner and the commissioner of lobbying.
A spokesman for Environment Minister Peter Kent said Mr. Carson broached the topic of water issues in First Nations communities when he met the minister last month.
But the spokesman added Mr. Carson wasn't lobbying the minister on any company's behalf.
Before that, Mr. Carson met senior political staff in the office of Indian Affairs Minister John Duncan on Jan. 11 of this year to discuss a First Nations water filtration project and H20 Professionals, officials in Mr. Duncan's office said.
Mr. Duncan's office said the January meeting involved Kym Purchase, the minister's director of policy, and Ted Yeomans, his director of parliamentary affairs.
Mr. Yeomans is a former assistant to MP Pierre Poilievre, Harper's parliamentary secretary.
"Mr. Carson briefed the staff on the proposed water project," Michelle Yao, Mr. Duncan's director of communications, said in an e-mail. "Staff provided publicly available information to Bruce Carson and recommended he work directly with First Nations."
Ms. Yao described the meeting as standard practice. "Minister's staff regularly attend meetings with individuals and stakeholders," she said.
Mr. Carson also met Indian Affairs officials four times between September and December, 2010. The department says it has not awarded any contracts to H20 Global Group, the company Ms. McPherson worked for.