The existence of a binder of calendars, chronicling Duffy's life over four years, was revealed in RCMP documents filed in court his week.
It raises a host of new questions about how much the Prime Minister's Office knew about Duffy's movements, at a time when the former Conservative senator's expenses were under the microscope.
"The calendar is quite detailed and contains notes of Sen. Duffy's travel, meetings, teleconferences, social events, holidays, noteworthy current events, speeches, and political interactions," Cpl. Greg Horton wrote in a court filing.
In early February, the Senate asked independent auditors to look into Duffy's expenses following allegations he was improperly claiming a home in P.E.I. as his main residence. Some time that month, Duffy sent the binder of calendars via courier to Nigel Wright, then Harper's right-hand man.
"Mary and I copied and redacted my four years of diaries; added a summary of my days in P.E.I., and pics of the cottage under construction etc. and sent it to Nigel by Purolator," Duffy wrote in a Feb. 20 email obtained by police.
Duffy never gave those calendars to the Deloitte auditors and they finished their report in May pointing out publicly the many questions they still had about Duffy's whereabouts and expense claims. Still, the Conservative Senate leadership did not demand more detail and backed a report that contained no criticism of Duffy.
The news broke shortly afterward that Wright had given Duffy a $90,000 cheque in March to repay questionable expenses.
A Senate committee started scrutinizing Duffy's expenses again, this time connecting more dots with the help of detailed information from Senate finance officials. The matter was forwarded to the RCMP.
By mid-June, the RCMP were talking to Wright's lawyers, who said Wright was willing to meet with investigators. It is unclear whether that has occurred.
Wright's legal counsel did not send the binder of calendars to the police until more than two months later.
The Canadian Press put questions to Wright about the documents through his lawyers. Peter Mantas responded Wednesday that they "could not comment on the matter." The Prime Minister's Office said Wednesday the Duffy file was "handled by Nigel Wright and he has taken sole responsibility."
"We are assisting with ongoing investigations into this matter," said spokesman Stephen Lecce.
Opposition parties have alleged that Harper's office has been covering up the extent of its knowledge about the Wright-Duffy transaction.
"Clearly a great deal of negotiations must have been going on to have such an extensive paper trail, and it was a paper trail inside the Prime Minister's Office," said NDP ethics critic Charlie Angus.
Liberal Leader Justin Trudeau pressed the government in May to release any documents about the Wright-Duffy transaction, a few days after Wright had quit the PMO.
"Will the government commit to releasing this and any other email or document, electronic or otherwise, that relates to the secret deal between the PMO and their friend, Sen. Duffy?"
Harper's office has so far not acknowledged the existence of any documents currently or previously in its possession. Wright has said he told three other staff inside Harper's office about his intention to give Duffy money.
Duffy has said he will not comment.
The RCMP have outlined four areas of investigation as they file production orders for documents: The $90,000 transaction between Duffy and Wright; Duffy's housing expense claims; his travel expense claims; and $65,000 worth of Senate-paid contracts Duffy provided to a friend over three years.
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