On the surface, Jim Balsillie would appear to be every sports league's ideal for a prospective owner - rich, well-connected and brimming with enthusiasm for the game.
Yet the National Hockey League appears determined to avoid the co-CEO of BlackBerry-maker Research in Motion. And a few people in the know say they can see why.
Balsillie's approach is all wrong, they say, from insisting on moving the objects of his desire north of the border to making moves that appear to come as a surprise to NHL commissioner Gary Bettman.
That's why the looming battle over the Phoenix Coyotes - Bettman said Balsillie's US$212.5 million offer for the troubled team will be the "subject of litigation" - is about so much more than just the future of one struggling hockey club.
For Bettman, it's about asserting his authority over the league's agenda and showing other owners no one can highjack it to suit their own goals. For Balsillie, it's about bringing a hockey team back to a region that loves the game despite the NHL's stubborn refusal.
But to some extent some it's also personal.
"(Balsillie) has alienated himself to the old guard because he doesn't follow the board of governors' rules," a former minority owner of an NHL club said Wednesday on condition of anonymity. "He doesn't seem to want to play by the rules.
"He's very brash."
Of that there's no doubt.
Balsillie's offer for the Coyotes is conditional on his bringing the team to southern Ontario and is his third attempt at buying an NHL team. He says the reason for his interest is straightforward.
"I'm clearly just a passionate hockey fan," Balsillie said this week about his pursuit of the Coyotes. "I don't have to tell anybody here it's the greatest game in the whole wide world."
Deals for the Pittsburgh Penguins and Nashville Predators fell through over plans to move them north.
This bid - for a club filing for Chapter 11 bankruptcy protection as the Coyotes are doing - could manoeuvre around league rules, which Bettman has used to fight off attempts to move other teams.
"Bettman has - if he hasn't said it in words, certainly in his actions - said, 'It will be over my dead body if a team moves from the U.S. into Canada,"' said the former owner. "He believes that the southern U.S. is not the future of hockey, but the growth area of hockey. What (Wayne) Gretzky did in L.A., Bettman thinks can happen everywhere."
One longtime, well-connected sports executive understands Bettman's reluctance to let the Coyotes move, since abandoning Phoenix could open up the floodgates for other struggling teams to do the same.
But at the same time, he could only shake his head at how Balsillie is going about things.
"For the life of me, I don't understand the strategy on this one," he said. "There's six and a half billion people in this world but there's still 30 people he's got to get along with. And those 30 people are going to say 'What the hell is going on here? You didn't even phone the commissioner and say you're going to do this? Here's my offer, take it or bring me to trial?'
"It doesn't make a whole bunch of sense."
While owners are competitors, he added, they're also partners and "if you let somebody who's not in the game just say, 'This is what I'm going to do and screw you,' they may think that's what's going to happen later at some point and time, too."
"He didn't help himself by making so many people unhappy the last time," he continued, "and people have long memories."
That's why another longtime sports executive with a background in dealmaking said Balsillie's's approach has been flawed from the start.
"In business, people don't like surprises," he said. "I happen to like Jim Balsillie, but he just shot himself in the head."
"If you don't have Bettman onside, who's going to support you?"
He said a wiser approach for Balsillie this time would have been to buy the Coyotes for far less money, lose money there for a couple of years and then try to make the move.
"Then he becomes a member of the club, and he can go to his partners because he's tried, and say, 'Look guys, I've blown $40 million here, I tried. It doesn't work, let me move it,"' said the dealmaker. "There's a better chance that way because he's built a bond with those guys. It's called politics.
"He takes them out to drinks, when his team plays in Toronto he sits down with (Larry) Tanenbaum, you go around, they suddenly find he's not a guy with horns and a pitchfork.
"Doesn't that make sense?"
Tanenbaum, chairman of Maple Leaf Sports and Entertainment, the parent company of the Toronto Maple Leafs, is said to be completely opposed to Balsillie's attempts to bring another team to southern Ontario and will be willing to fight his attempts tooth and nail.
How many other owners would back the Maple Leafs and how many would like to see another team tapping into the region's fanbase is unclear.
There's no doubt about where the NHL Players' Association stands on the matter.
Union head Paul Kelly, speaking at the IIHF World Hockey Championship in Switzerland, reiterated his stance that the league should look to southern Ontario first if the Coyotes have to bail on Phoenix.
But he said he's not sure how the league will receive Balsillie.
"I'm certainly well aware that (the league) doesn't like to be strong-armed," said Kelly. "And the league believes that it has a number of legal and technical manoeuvres that it can take to block anybody that tries to forcibly enter the ownership group. ...
"I've never met the man, but I've talked to him on the phone and I sensed his passion for the game. I do think that it's somebody that would be worth considering, but again, there's a lot of politics and there's a lot of history here that I'm not really in a position to comment on."
- With files from Donna Spencer in Calgary and Chris Johnston in Bern, Switzerland.