Duffy had a labour lawyer!? ….or, Whyever Did Nigel Write a Huge Cheque to Someone He Didn't Like?

What drove Nigel Wright to attempt to satisfy Duffy's demands, then ultimately pay them out of his own pocket?  The fact that Janice Payne, one of Canada's leading experts in labour law represented Duffy in his negotiations with the PMO/CPC may provide a clue.

The following is reasoned conjecture.  Any and all factual information that might illuminate or dispel the conjecture would be welcome.
Nigel? Mike? Steve? Irving? ...Feel free to jump in at any time

Some motivations that are fairly well understood and accepted:

• In the '08/'09 winter of discontent and facing a potential election, the Conservative Party of Canada would welcome a high profile promoter and fundraiser to their ranks. 
• Frankly, Mr. Duffy wanted the Order of Canada but he made it known that an appointment to the senate might be attractive too.

But there would have been a practical problem in meeting the needs of both these parties:

• A senator's salary of $135 K per annum would hardly maintain Mr. Duffy in the manner to which he was accustomed.  As CTV's senior political analyst it's likely he was pulling down in the neighbourhood of $500 K a year. (By comparison, we know that Don Cherry commands about $800 K and his job description doesn't require that he be informed, intelligent or even civil.)
• In cash alone, the change in employment from pundit to politician could cost Duffy over $300 thousand per annum, which --even for the most public minded of servants-- amounts to quite a lot of potatoes.

So:

• It would make sense that the terms of Mr. Duffy's move from well-paid broadcaster to more modest sober second thinker might need to be lubricated by some additional financial accommodations.  Some creative incentives might have to be arranged.  Such an arrangement would have to be contrived by senior people with access to considerable resources.  Some fairly concrete understandings and assurances might need to be communicated.
• One easy option available to the negotiators would be that the CPC, might provide some financial reward for the Duffster's considerable fund-raising and promotional capacities.
• It would make sense that very senior people in the party and possibly even the PM himself might need to be involved or privy to any discussions of financial contribution by the CPC.  
• As a practiced facilitator, PM king-maker and senior director of the Conservative Fund of Canada, Nigel Wright could easily be the person tagged with the responsibility of crafting a mutually beneficial deal. Indeed, it's not beyond imagining that Mr. Wright could have even initiated the discussion to bring the broadcaster into the CPC fold. 
• It's not beyond imagining that self-declared Party Bagman, soon-to-be-Senator Gerstein might also have had a hand in putting the pieces of the puzzle together.
• Duffy was already in the midst of contract talks with CTV. so he would be very aware of his market value. He was a man who spent freely and money mattered.
• If the move to lower-paying public service were to be attractive, some sweeteners would help.  So, what sorts of inducements might be available to whomever was at the table that might offset any diminishment of a senior broadcaster's pay packet? 
• Well first, not just one job, but two could be offered: There's Senator for PEI but there is also fundraiser and policy promoter/explainer for the CPC.
• The prestige of the Senate would, of course, be an inducement.
• The Senate job is good until 75 so there's a longer run than what television offers.
• The Senate gig is not too demanding and there's a damn fine medical plan and pension.
• There's a healthy office budget and "Senate work" is not well defined and even less well monitored.  A senator can hire their own "consultant" for quite nebulous purposes, for instance.
• Then there's a possible housing allowance for living in Ottawa.  Other senators draw on that --the Liberal's Harb, for instance so they can't say anything.  And work for The Party would require a productive fundraiser to be handy to a major airport like Ottawa. 
• Trips back and forth to the cottage on The Island could also be expensed.
• As for the work for the party, the CPC or the riding associations can cover all travel and other expenses - There might be speaker fees or perhaps finder's fees for money raised by a skilled fundraiser.  Things like that might legitimately be expensed when someone is out there doing trench work for the party.
• All in all, the party would not be without the means to keep a valuable person 'whole' --in short, to ensure that there would be no net loss from a senior broadcaster's income.
• As Revenue Canada could attest, the Old Duffster himself was adept at creative accounting and might have some suggestions of his own.
• Since Mr. Duffy did actually give up his job as a broadcaster and become a Senator and active CPC fund raiser, it would make sense that some sort of understanding would have been achieved --an agreement, if you will, that might have been consummated by a firm and happy handshake among new compañeros.  It might be imagined that Mr. Duffy might understand that he was moving into a new employment situation -not just for the Province of PEI, but also for the Conservative Party of Canada and quite possibly, even the PMO.
• It would not be beyond imagining that, if there were a handshake, then two of the hands could easily have been Mike Duffy's and Nigel Wright's. 
• It is also not beyond imagining that any potential agreement might include a mutual understanding to keep the whole thing on the down-low to ensure that no other new senators-who-will-remain-nameless would demand a similar arrangement.  

Once achieved, such a quiet arrangement could perk along to everyone's mutual satisfaction for several years.  However, the bookkeeping involved in filing expenses with two employers could lead to confusion and result in mistakes.

If one imagines the above to be conceivable, then, when criticism of Senator Duffy's inappropriate claim for his Ottawa residence went public and he was informed by the PMO that he was expected to repay quite a lot of money --cash that he might not have, one might also imagine:

• that Senator Duffy might feel betrayed and outraged.
• that Senator Duffy might hire a skilled labour lawyer to represent his side of an agreement that he thought he had secured. (If Duffy were smart in this imaginary scenario, he would have kept notes or other communication records that captured important elements of the understanding.) 
• that Senator Duffy would look to have his reputation protected by having the PM and senior senators give public assurance that his interpretation of residency and expenses was on the up and up - an assurance that may well have been assumed on his taking on the job.
• that Senator Duffy would look for promised job security in an assurance that he would not be disqualified from the Senate because of residency.
• If Senator Duffy were to demand compliance with the original terms of his "employment", it might prompt someone with knowledge of those undertakings to immediately observe:  “Let this small group be under no illusion, I think that this is going to end badly,”  …even more-so if Duffy was able to cite written undertakings.
• that, even if inappropriate past expenses were paid out, there remains the problem of Mr. Duffy earning much less than before, so Senator Duffy might seek assurance that, if ever the rules should change, he would be once again 'made whole' by expensing his Ottawa living costs.
• that a principled Nigel Wright, while disgusted at someone's insistence on their "entitlements", might none-the-less feel bound by 'commitments' made.  (There is the possibility of even greater motivation for Mr. Wright if there were some record of any commitments made.) While disgusted, a rich and publicly responsible man like Mr. Wright might even be moved to spare both taxpayers and party contributors the cost of a deal gone sour in his hands.
• and, since he was now suffering a dramatic cut in pay, Senator Duffy might want his labour lawyer's legal costs covered for all these amendments to his terms of engagement.
• having saved the party contributors and the taxpayers from Senator Duffy's inflated sense of entitlement, Mr. Wright might be motivated to remain silent.

Mike, Nigel, Steve, Irving - any comments?