I love how people think he is suddenly poor. The team would probably worth over $1 billion right now if they were in Hamilton. If he had spent say $300-$350 million to buy and move the team (payoff Glendale and Buffalo) His net worth would be much higher if he had pulled it off.
Obviously the league didn't seem too interested in allowing Balsillie to do that after a certain point but I agree with your overarching point: If there was a universe where the NHL and Balsillie came to an agreement to put a NHL team in Hamilton (relocated or otherwise), he'd be worth much more than what he is now. In fact, biopics like
Blackberry might even have a very different take on the man. Both his actual net worth and his reputation took huge hits for how it all shook out.
The history of business people trying to bring the NHL to Hamilton seems to center on those businesspeople not wanting to play by whatever rules the NHL sets. The 1990 group wanted to treat the expansion process like a negotiation: "You've told us you want us to pay _x_ in expansion fees, but what if we pay _y_ and _z_ over these periods...." Balsillie's approach could have been a whole movie separate from
Blackberry if the director wanted it to be.
I still think the 1990 bid was the bigger missed opportunity for Hamilton. Copps was still relatively new at the time and had a certain "shine" to it associated with its Canada Cup moments. The potential for growth was great, and with Harold Ballard having just recently passed away, the Leafs opposition powers were never going to be softer.
The arena was barely 7 years old. Only the core of Westgate was built to that point and the city had been assured both times that the league would have a sale done in short order. Allowing the city to get the money back. Hulsizer's bid was reliant upon the $100 million "parking deal" that Goldwater Institute rained cupcakes over. Jamison's bid was reliant upon a consortium of people that had no clear dominant shareholder.
I feel like Reinsdorf was the best chance. It felt like a rotating series of clown cars after that. Notwithstanding the issues Merulo may have, at least he really is very rich. He might as well be Jeff Bezos compared to the groups that were lining up for the Coyotes in the 2010s.