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Somewhere inside, Bruce Firestone is hurting.

He will not say so, but will admit that when Daniel Alfredsson scored the overtime goal that put the Ottawa Senators into the Stanley Cup final, "I was teary-eyed. I really love the team."

But you really can't blame Firestone if he feels a hurt along with the pride of knowing he was the man who brought the National Hockey League back to Ottawa. Because as the team embarks on its biggest step since joining the league in 1992, he is no longer part of it.

He bet the family company, Terrace Investments, founded by his father, Jack, in 1957, on a dream: landing an NHL expansion franchise to back an audacious real-estate play west of Ottawa.

Firestone won the bet — he and two friends, Cyril Leeder and Randy Sexton, were awarded an NHL team when they pledged $50-million they did not have — but lost the family company and his dream when financing it and a new arena proved beyond his means.

The idea was hatched when Firestone, then-CEO of Terrace, drove up and down the Queensway, the freeway that now runs from downtown Ottawa west to the site of Scotiabank Place, the Senators' arena, wondering how to make a big score in real estate.

"The 1980s were a go-go decade for real estate but at the end of the '80s a lot of new competition came on market from banks, mutual funds and pension funds," Firestone said. "It became a lot more competitive.

"I was wondering what to do next, so I got in my car and cruised up and down the Queensway. I thought of what Toronto had. They had a zoo and, well, they had an NHL team. I wondered if Ottawa were big enough for an NHL team."

By the end of his thinking, Firestone came up with the idea of an NHL franchise and its arena, called the Palladium in those heady days, spurring development of residential communities, office buildings and shopping and entertainment centres, all a good half-hour's drive to the Kanata farmlands west of downtown.

He took the idea to his two best friends and employees, Leeder and Sexton, one night after their beer-league hockey game. Both jumped aboard and helped sell the unlikely idea to the NHL.

Like just about everyone chasing a big play without solid funding, Firestone's plans rested on a lot of ifs — and when a couple of them came crashing down so did he. The biggest one, Firestone says, was then-Ontario Liberal leader and Premier David Peterson, who promised to build an interchange to his arena off the Queensway. Then, Peterson called an early election and Bob Rae and the NDP wound up in charge.

There went Firestone's interchange. Throw in the crash in real-estate values in the early 1990s and any potential investors in the arena were gone, too.

"It took $30-million to build the [interchange] and there was a $50-million writedown on the land," Firestone said. "So we lost $80-million and that's the reason we lost the team."

Rod Bryden, a hotshot deal maker, came in to rescue the arena deal and wound up with Firestone's majority share in Terrace at a huge discount. By the time what is now called Scotiabank Place opened in 1996, the only one of the Three Amigos left with the team was Leeder, who is still with the Senators as chief operating officer.

Sexton was fired as general manager a month before the arena opened and now works for the Florida Panthers.

That, Firestone admits, is when he did feel a real hurt.

"I've been asked a number of times if that was a tough time," he said. "It was. I worked with Cyril Leeder and the team for many years. Leaving those people was very tough.

"I would be kidding if I didn't say there were a few years where I wandered the wilderness so to speak."

Firestone eventually put his career back together.

Today, he teaches a couple of architecture classes at Carleton University and is entrepreneur-in-residence at the University of Ottawa. He went back to school a couple of years ago to get his commercial real-estate licence so he can buy and sell the properties he advises high-tech companies about in his consulting business.

But, as Firestone will tell you, that was just his career. He never lost his personal life. Losing Terrace put a strain on his relationship with his sister, Brenda, and brother, Peter, but, as Leeder says, "that is kind of behind the family now."

Marriages are often casualties of business meltdowns but Firestone and his wife, Dawn, who have five children, are still together. His friendship with Leeder and Sexton survived, too, and they regularly get together at an Ottawa bar to talk about their baby, the Senators.

"Dawn was really a trooper through the whole thing because it was tough on her," Leeder said. "I feel pretty lucky to still be here. I've got the greatest job in the world. I owe a lot of that to Bruce, who gave me my first real job. From the personal side, I wish those guys were still part of the team."

That's okay, Firestone says, because he's at a place now where he can look on with pride. Which he does, from the suite he and his sister still own at the arena.

"It's been a real privilege to watch the team," said Firestone, who does not spend any time thinking "what if?"

"I'm an entrepreneur. I've had some successes and some failures. Most entrepreneurs tend to look forward to their next challenge."