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Nigel Wright, former Chief of Staff to Prime Minister Stephen Harper arrives at his condo building June 17, 2014 in Ottawa.Dave Chan/The Globe and Mail

It's a rarity in Canadian politics and all the more compelling because it's taking place against the backdrop of a tight election campaign.

A former senior aide in the Prime Minister's Office, Nigel Wright, is taking the stand at a criminal trial. His ex-boss, Stephen Harper, is locked in a three-way political race for 24 Sussex.

Mr. Wright served as chief of staff to Mr. Harper – a position that sits at the apex of federal politics – until May of 2013 when he resigned after it came to light that he'd given Senator Mike Duffy $90,000 to reimburse taxpayers for questionable expense claims.

The 52-year-old wealthy businessman, now working in London for Onex Corp., has returned to testify at Mr. Duffy's trial as a witness for the prosecution. Mr. Duffy, who was appointed to the Senate by Mr. Harper, faces 31 charges of fraud, breach of trust and bribery and has pleaded not guilty.

Here's Five Things to Watch for as the Duffy trial begins its third instalment Wednesday:

The E-mails:

Will there be new revelations? Donald Bayne, Mr. Duffy's defence lawyer, has already served notice in court that he plans to release internal e-mails between Mr. Wright and other Conservative officials.

Mr. Duffy has already alleged in the Senate that he is the victim of a "monstrous conspiracy" aimed at snuffing out controversy over his Senate expenses.

These electronic missives will offer new insight into the workings of the Prime Minister's Office under Mr. Harper and how it managed the Duffy scandal as the PEI senator came under increasing pressure to account for questionable expense claims. The e-mails could also provide new fodder for the NDP and Liberals on the campaign trail as they try to make the case that the Conservatives are too beset by scandal to merit another term in government.

The Defence:

Why Mr. Duffy and not Mr. Wright? Mr. Bayne will raise questions about an incongruity on the charge sheet: Mr. Duffy is accused of "corruptly" accepting the $90,000 payment and faces a bribery charge for this. Yet Mr. Wright, who provided the money, faces no charges. The RCMP dropped its investigation into him more than 16 months ago.

The defence argues Mr. Wright came up with the repayment plan and that Mr. Duffy was pressed into taking the money in order to reimburse taxpayers and put an end to the political controversy.

Sources say Mr. Bayne has planned days of cross-examination of Mr. Wright that will go well beyond the discussions of the $90,000 to make the defence case that Mr. Duffy did not break the rules of the Senate with his claims for living allowances. The defence has argued that requirements for senators in the Constitution forced Mr. Duffy to list his PEI cottage as his primary residence, and that Senate expense claim rules were vague and broad, allowing Mr. Duffy to charge taxpayers to fulfill his parliamentary duties.

The Prosecution:

In short, can the Crown make the bribery charge stick? Sources said the prosecution will attempt to persuade Judge Charles Vaillancourt that Mr. Duffy engaged in a pattern of criminal behaviour culminating in the payment from Mr. Wright that allowed the senator to pretend he had personally reimbursed taxpayers. "What we'll be looking for is the circumstances of that payment," said Michael Spratt, an Ottawa lawyer following the case. "Why was it made? … Who was involved in that decision and, most importantly from the Crown's perspective, what sort of strings were attached? And do any of those strings lead to corruption that can fall under the bribery count of the Criminal Code.

Nigel Wright:

The Crown needs to keep Mr.Wright's credibility intact because he is one of their star witnesses. So while he wrote the cheque that drew the PMO into this entire scandal, he faces no charges in the matter. "They have to walk the line between Nigel having no corruption and somehow it developing [later] when Duffy accepted the money," said Mr. Spratt, with Abergel Goldstein & Partners. He said this only holds up if "you accept that Mr. Wright gave it, without any corrupt intent whatsoever, to keep the taxpayers whole and [yet] somehow it was accepted by Mr. Duffy under corrupt circumstances."

Stephen Harper:

Will Mr. Harper be drawn into the maelstrom? The PMO, the Conservative Party and Mr. Wright have repeatedly insisted there was a firewall between Mr. Harper and the decision to give $90,000 to Mr. Duffy – and that the Tory Leader never learned of it until it was reported in the media in May 2013.

That line of defence came into question in late 2013 when an e-mail surfaced from Mr. Wright to his Conservative colleagues in which Mr. Wright said they were "good to go from the PM" on the Duffy repayment plan.

As recently as last week on the campaign trail, Mr. Harper said this does not implicate him, insisting those were "not my words."

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