Richard Peddie took over as president of the Toronto Raptors on Nov. 22, 1996, with ambitions beyond simply running an NBA team.
Fourteen years later, he announced plans to retire after helping build a multifaceted sports, entertainment and property development empire that has earned him both corporate praise and fan scorn.
"When I was Raptors only, [the priority] was getting the new product off the ground and getting an arena built," Peddie said in an interview Tuesday after revealing that he will step down as president and CEO of Maple Leaf Sports and Entertainment at the end of 2011.
"When the Leafs bought us, it was getting Air Canada Centre built and putting the two companies together. Then after a couple of years of what I call organic growth and getting everything settled, the board really challenged our management team with growing the business.
"That's what got us thinking of soccer and getting into our own networks, getting into Maple Leaf Square, all of those things were outgrowths of that challenge by the board."
There's no arguing that Peddie and Co. have brilliantly executed the business side of the equation, but for many fans of the Maple Leafs, Raptors and Toronto FC, it's the failure to build a winner in any sport that they will most be tied to his legacy.
Though the 63-year-old still has another year to go before walking away, the record on the ice, hardcourt and soccer pitch isn't pretty.
The Maple Leafs made two trips to the conference finals under Peddie's watch but have missed the playoffs the past five years and are on track to make it six in a row.
The Raptors have won exactly one playoff series in their first 15 seasons and it looks like Year 16 will mark the 11th time they fail to reach the post-season.
Toronto FC, meanwhile, has yet to make the playoffs in its four Major League Soccer seasons.
It's not a pretty list, and Peddie calls "not winning anything yet" his biggest disappointment on the job.
"The Nutrilite Championship for TFC doesn't count, that's nice to represent Canada in that and to go a little deeper in CONCACAF, but our vision is to win and we haven't won anything, division championships aside," said Peddie. "We're here to win cups and rings and we haven't done that yet."
As a focal point of fan ire, Peddie says between laughs that his skin has "definitely, absolutely" thickened over the years.
Fans have blamed him for meddling in team affairs, kowtowing to a board more interested in profits than victories, and a relentless greed in searching for new ways to bloat the bottom line.
He's learned to take the slings in stride.
"We're the most public private company in Canada, we have probably 50 [reporters] covering us on a daily basis. There's no company in Canada that gets that type of media coverage," said Peddie.
"It's a high-wire act — you have fans that pay good money to watch us on TV or live, buy our T-shirts and our hot dogs and they expect us to win. I don't fault them for that.
"When you go into this job you've got to be prepared for that, nobody is going to win all the time.... If you don't have skin that's thick enough for it you shouldn't be in the business."
Peddie said his departure has been discussed regularly as part of the organization's succession planning for the past four or five years, but that given his age, Dec. 31, 2011, was the right time to step away.
MLSE's board of directors has formed a search committee that will be helped by recruiting firm Korn/Ferry International in hiring a replacement. Internal and external candidates will be considered.
"You have to have good general managers and empower them to do the job," Peddie said. "Really, the job is more on the business side where you need to understand the hospitality business, marketing, branding, sales, finance, legal, retail, food and beverage, hotel, all of that.
"There's no one person who's an expert in all of that, you surround yourself with great people and know a little bit about that yourself."
Peddie will remain for a transition period with his successor and won't be reluctant to start new projects — the MLSE board recently approved a new series of five-year plans — or extend other employee contracts.
Tops in that regard is Raptors GM Bryan Colangelo, whose contract ends after the season. Peddie said in October that an extension was something the sides would "get to," and added Tuesday "that's got be dealt with in the time I have remaining."
"The board has instructed that's something I would have to do," he added.
Peddie conceded that talking about wrapping up his work was "bittersweet" since becoming a basketball executive was something he aspired to.