Court documents released Wednesday shed new light on the extent to which officials in the Prime Minister's Office were involved in the deal between former chief of staff Nigel Wright and Senator Mike Duffy to repay Duffy's ineligible expenses.

But the documents, filed by the RCMP's lead investigator on the Senate expense investigation in a bid to have the court order the release of further documents and data, also contain some intriguing information that raise fresh questions.

Here's a look at three of those questions:

Why were Nigel Wright and other senior Conservatives so worried about what Deloitte or the Senate might find in Duffy's personal files?

In a Feb 20 email sent to Chris Woodcock, Benjamin Perrin "and other PMO employees," Wright notes that the next day, he will receive "redacted copies of [Duffy's] diaries and other info" related to his primary residence claim.

"Our team will have to look at that to see there is anything in it that we would not want his lawyer to send to the Senate steering committee," he notes. "Maybe it will persuade us to let him take his chances with Deloitte's findings."

It's not clear precisely what "it" Wright was referring to, or why he believed that Duffy's redacted records could contain information that PMO would rather not find its way to the Senate committee.

In any case, whatever "it" was, it failed to "persuade" Wright and the others to "let him take his chances with Deloitte's findings" — a phrase also laden with tantalizing ambiguity. Was Wright suggesting Duffy's travel diaries could hold the key to total exoneration for the senator?

Or did he suspect the newly revealed record would bolster the case against him to such an extent that PMO could walk away from the negotiating table and leave him to his fate?

In an email sent a week or so later, Wright warned his colleagues that having Duffy's lawyer write to the auditors to "specify the amount of expenses owing" could "give Deloitte an excuse to ask for documents from Duffy again," which suggests a continuing reluctance to give the auditors access to Duffy's files.

A month later, an offer by Duffy to meet with those same auditors set off still more alarm bells at PMO, particularly when the auditors advised the Senate administration that they were keen to take him up on the invitation, and would also "request documents ... that he had yet to provide."

According to the RCMP summary, Senate administrators were fine with a meeting that "would be helpful to Deloitte," even if it could result in a "short delay" in completing their report.

When alerted to the news via an email from Senator Stewart Olsen, however, Wright had a very different reaction:

On April 22, Senator Stewart Olsen e-mailed Chris Woodcock regarding Senator Duffy.

She stated: "Duffy is asking to meet with Senate audit committee or the auditors themselves. Do you know why he wants to escalate?"

The e--mail was forwarded to Nigel Wright who responded: "Never heard of this. Is bad."

An email from LeBreton aide Chris Montgomery the following day reveals that the steering committee decided to tell Duffy that, as the audit had "concluded" (which, judging from the response to the auditors to Duffy's offer, was not, strictly speaking, true), and, a result, he wouldn't get to meet with the auditors after all.

The move to kibosh a face-to-face chat between Duffy and the Deloitte team prompted LeBreton to state, via email to PMO staff, that "her only concern" was Duffy himself.

"Even though he claims he is careful in what he says and does, the evidence is the opposite," she noted. "We have to be very careful what we say to him."

From her perspective, that caveat was likely confirmed on May 9, when Duffy showed up at a meeting of the internal economy committee hours before the Deloitte report was scheduled to be released, and, in her words, "handed the Libs the reason to go to the police":

On May 9 at 9:40 a.m., the day the final Deloitte Report and Senate Report was going to be made public, Senator Stewart Olsen wrote to Chris Woodcock and Patrick Rogers regarding "Duffy":

"He needs to get out of committee. He just handed the Libs the reason to go to the police"

[Senator Duffy made comments in committee about having been contacted by Senator Tkachuk during the audit process, about claiming per diems in error while on vacation in Florida].

Senator LeBreton then wrote to Nigel Wright: "Hi Nigel -- Is there any way we can get Duffy to stay away and most importantly avoid any media. By his appearance at Internal Economy he has really complicated our day!".

Chris Woodcock followed up with: "I spoke to Duffy. He won't do any media and will stay away from the Chamber today."

As is clear from the above excerpts, the mere idea of Duffy handing over documents to Deloitte or the Senate standing committee — or, indeed talking to the Deloitte auditors, or opening his mouth at a closed-door, but all-party committee meeting — was enough to trigger panicky email exchanges between Wright, Woodcock, LeBreton and other senior Conservatives.

The still-lingering question remains why — and, indeed, whether PMO is still spooked by what Duffy, or his documents, could reveal.

What elements of the negotiations between PMO and Duffy never actually made it into writing?

Although the application filed by the RCMP in support of the latest production orders includes voluminous excerpts from internal emails between senior PMO officials, Senate staff and other in-the-loop parties, a few of those excerpts seem to suggest that more contentious issues may have been deliberately taken offline, either by moving the discussion out of email, or explicitly declining to make certain promises in writing.

The most noteworthy examples, with emphasis added:

A Feb. 15 email from Wright to Perrin et al:

Based on Montgomery's response it is clear to me that Ben and I should brief Senator LeBreton directly. Chris simply does not believe in our goal of circling the wagons. Because of this lack of buy in, it was impossible to discuss meaningfully the parliamentary strategy .... will work with Ben to get something for the Prime Minister tonight

A Feb. 20 email from Wright to Woodcock, Perrin and other PMO staffer:

What I have said to Mike, and others can, but I don't see a need to put in writing, is that we believe he meets all residency requirements relating to his ability to sit as a Senator from PEI and that we will defend his Constitutional residency qualification categorically. ..

From a summary of Feb. 20 events:

Nigel Wright proposed to Benjamin Perrin that they relay the media line to Duffy over the phone, and added, "I don't like the optics of our sending lines to his lawyer. We could walk him through the support we would provide."

A Feb. 21 note from Wright on email from Duffy's lawyer on the proposed agreement:

I have been specific with Sen. Duffy that a "senior government source" will make a statement on the day of his statement to the effect that there is no doubt he is qualified to sit as a Senator from PEI. The PM will also give this answer if asked, as will other authorized spokespeople for the Government. That is because it is true. There will not be a written acknowledgement.

From a summary of Feb. 22 events:

Benjamin Perrin followed up with an e-mail to Nigel Wright advising that Janice Payne wanted the agreement in writing, and stated, "I explained that was not happening. We aren't selling a car or settling a lawsuit here. She seemed to get it eventually..."

There is, of course, nothing particularly nefarious in conducting more delicate negotiations in person or by phone, rather than through email.

Still, given how much we're obliged to rely on written evidence to draw conclusions on how deeply the PM's office — and, indeed, the PM himself — were involved in the negotiations that led to the $90,000 payment, it seems fair to ask whether the most crucial communications made it into the paper trail.

What was the deal with that $60K in 'unrelated' legal fees Gerstein suggested Wright 'file a claim' for reimbursement?

Although almost certainly irrelevant to the main plotline, it's hard not to idly wonder just what "unrelated" legal matter arose during Wright's tenure at PMO that cost him $60,000 in out-of-pocket legal fees, as he suggested while being interviewed by the RCMP.

Whatever it was, it sounds like he didn't take Senator Irving Gerstein's suggestion to "file a claim" for the money — which, when added to the $90,000 he gave to Duffy, would mean that his two years of public service at PMO ended up costing Wright at least $150,000.