THE DEALMAKER: As CEO and president of CanWest, Leonard Asper polished his negotiating skills long before he took over his current position in 1999.

“I’ve been learning about deals since I was very young,” says Asper, whose father, Izzy, founded CanWest, one of Canada’s leading media companies. “I spent many years in the room with my father, watching and learning from his successes and mistakes.”

Those lessons helped Leonard Asper develop a simple set of negotiating rules that have served CanWest well over the past decade. Among the company’s biggest accomplishments under his leadership has been the $1.5 billion deal for Alliance Atlantis specialty channels, which was finalized in January 2007.

Asper credits the deal’s success to CanWest’s patience and his team’s comfort level working with Alliance Atlantis’ executives. “We had a lot of time to conceive it,” he says. “Alliance Atlantis had been a target of ours for five to 10 years. It has been a smashing success. Revenues are ahead of where we thought they would be. We’re thrilled.”

Dealmaking “is like a football game plan,” says Asper. “You can prepare, and everything can be going great until your starting running back or linebacker gets injured. With negotiations, you can set hard-and-fast rules, but things change once you get in a room.”

KEY DEALS: $1.5 billion deal for Alliance Atlantis specialty channels; $3.2 billion purchase of Hollinger Inc. properties in 2000.

DEALMAKER DOS: “You have to get up front what everyone wants out of a deal. You have to look at the long-term benefits, but also protect the downside.”

DEALMAKER DON’TS: “Don’t get too cute. Don’t overcomplicate things. Never try to put one over on people; they will learn what’s going on during the negotiations, and that’s when the deal goes sideways.”

TOP DEALMAKERS ENCOUNTERED: “My father and (CanWest co-founder) Gerry Schwartz.”