If Leonard Asper could go back in time, he'd probably change a lot of his decisions at CanWest Global Communications, starting with that fateful day in 2006 when he climbed into bed with Goldman Sachs.
The unholy marriage of the Winnipeg media scion with America's most ruthless investment bank resulted in one of the most horribly lopsided contracts since the Dutch bought Manhattan - a deal so bad that to this day it hangs, like a foul stench, over the courtroom where lawyers now fight over the carcass of the late Izzy Asper's once-grand empire.
Everything comes back to Goldman. To follow the twists of CanWest's restructuring - it has been operating under protection from creditors since October - you'd never know that Canada is a country in which, technically, it's illegal for a foreign entity to control media assets. All roads lead to 85 Broad St., New York, N.Y., 10004.
Shaw Communications wants to buy CanWest's television stations, and Friday received the court's blessing to do so.
But will Shaw actually follow through with the deal? Only if it can win a bruising fight with Goldman that's almost certain to be decided by a judge.
A second group led by Catalyst Capital, a Toronto investment fund, had put forward a rival offer to Shaw's - and pitched it on the basis that its proposal kept Goldman satisfied.
A third player, Quebecor Media, was interested in the assets but pulled back.
Why? Because it was asked to sign a non-disclosure agreement that would have prevented it from talking in advance to Goldman.
Only a fool would try to take over a TV station in Edmonton if he couldn't chew it over with the Masters of Wall Street first, right?
Perhaps it's worth a quick review of how we got to this state of affairs.
In early 2007, CanWest made a $2.3-billion acquisition of Alliance Atlantis Communications, mostly because it coveted its clutch of cable channels.
For a company that used to make its living airing The Simpsons and Everybody Loves Raymond, owning the History Channel was a high-brow venture.
Unfortunately, it was also an expensive one; CanWest had no ability to borrow that kind of money, and Alliance management opted for cash, not CanWest shares. (Now those guys knew what they were doing.)
Thus was born the putrid deal between CanWest and Goldman, which Mr. Asper famously described as "renting" the investment bank's balance sheet.
Though complicated enough to confuse a quantum physicist, the contract could be summarized as follows: CanWest retained approximately 35 per cent of its television business, plus voting control, plus the ability to earn a bigger stake over time, depending on how much the business earned. Goldman inherited 65 per cent of the business, plus - crucially - a put option that gave it the right to sell its stake back to CanWest at a predetermined price, for a guaranteed return.
You can see the problem with this.
One party - Goldman - had a great deal of upside, but limited downside. CanWest, on the other hand, had all of the pressure of trying to squeeze as much out of the assets as possible, but all the risk if it went badly.
CanWest shareholders, events later proved, had unlimited downside: Their shares are now essentially worthless.
The "billion-dollar put," to borrow a phrase from BMO media analyst Tim Casey, has been like a noose ever since.
Now it's up to Shaw to try to rip up the deal.
This, Mr. Casey says, might be a good result. Whatever your opinion of the Aspers or CanWest, it hasn't been a healthy thing for the Canadian media industry to have one of the largest private TV networks and the largest daily newspaper chain owned by a company without two dimes to rub together.
Gutting the Goldman contract also provides a nifty solution for the CRTC, for whom the investment bank's power in an ostensibly Canadian-controlled media company has become an embarrassment.
And as for Leonard Asper? A Shaw victory, more likely now than it was a week ago, would mark the end of his family's role in CanWest. That would be a sad day for him, but consider it a hard lesson learned. If you have to "rent" something from Goldman Sachs - you probably shouldn't.