On Saturday mornings, Tim Leiweke has a routine. He gets up early, as he does every morning. He goes to the gym at the Ritz-Carlton Hotel and climbs the stairs to nowhere for an hour. He’s been living in the Ritz since his arrival in May. His wife, Bernadette, has remained in Los Angeles, helping plan daughter Francesca’s wedding in mid-August. She’s marrying journeyman Troy Bodie, who was signed a week ago by the Maple Leafs. Once married, toute la famille will move north. But for now, Leiweke is alone. Working out is a focus. The 56-year-old has lost 40 pounds since January. He takes in his laundry. He picks up the dry cleaning. Putters around for a bit. Around 10:30, he sets out. The most powerful man in Toronto sports walks for three or four hours every Saturday and Sunday, randomly plotting the city in his mind. One day, he walked out toward Exhibition Place, looking for a bar he’d heard Toronto FC fans gather at on game days. “It took a while for me to figure out a way across the railroad tracks.” He found the bar. Now he’s forgotten the name. He leans toward the door of his office and calls out to his receptionist. “Barb, what was the name of that bar that our fans go to at BMO Field?” Muffled reply. “Exactly. The Brazen Head. Awesome place.” Leiweke is impressive in front of a group. One-on-one, he’s Clintonian. You get hit with the sharp smile and the individually tailored compliments straight off, and you’re thinking, “Here we go.” But after 15 minutes, you’re swaying in place. A half-hour in, you’re wondering about job openings. The key to this charisma is the apparent guilelessness of his enthusiasm, the easy confidence. He throws himself down on a couch, body posture wide open, slapping his knee to pound out the syllables of his key points. He has a reputation as a crier. He’s embraced that. On the possibility of winning a Stanley Cup: “I gotta convince everyone around here. Think about it. Dream about it. Get tears in your eyes just imagining what it would do to this city.” Leiweke has set off in the direction of success, and he’s leaving laggards behind. It was on one of these long solo marches that he mapped the championship parade route. When he first drops it into conversation, I think he’s speaking metaphorically. Then unprompted, he brings it up again. “You mean, you have the actual route?” “Right.” I press him for the details. He tries to drift off into another topic, but keeps being dragged back. He wants it to start somewhere uptown. He mentions Varsity Stadium non-specifically. He points out that the waterfront is nice in June, and might be a logical ending point. His real worry is spacing. “If Chicago had one million people, Toronto will have two.” I’m sitting there thinking, ‘Does this guy know how this is going to play?’ I ask him if he can be more specific. “That I won’t say,” Leiweke says. “That’s for my mind.” I leave his office about an hour later, and check my phone. I discover that he’s told the same story earlier in the day to Bloomberg News. This is the first lesson of Tim Leiweke. He has come to Toronto to win things. More importantly, he has come here to write himself into history. He already has that route plotted in his mind as well.