The leather-bound appointment book lies in the centre of his desk, the edges perfectly aligned. There is a cell phone, parallel with two television remotes, not one a degree out of place.

Around Toronto Maple Leafs president Brendan Shanahan’s office there are some pictures you’d expect from a Hall-of-Fame player turned executive (lifting the Stanley Cup with the Red Wings) and some you might not (shaking hands with Bill Clinton and Stephen Harper).

There are books on business innovation: “Good to Great” by Jim Collins, and on sports innovation: “Big Data Baseball,” by Travis Sawchik.

But the 2015 edition of the brown, plush American Express appointment book takes pride of place. He fills it out himself, in ink, a habit he began when the high school graduate got his first real job, working alongside the league’s Ivy League trained lawyers at the head office in Manhattan. They go four years back now and the 2016 edition is already waiting at home.

He’s aware all this can be done digitally, but he likes the ritual and the permanence of the paper and pen.

“I’m more inclined to write stuff down, log things,” he says. “After you leave I’ll write down we spoke.”

Shanahan pulls the back catalogue out of a cabinet behind his desk. He can flip through them and find out what he did on say, Aug. 16, 2013: “Here’s the workout I did, took girls swimming, went to the golf range … had Jim, Sheila, Joyce over for dinner …”

The one from the summer of 2015 is presumably, pretty full. May 20: “Gave Mike Babcock the longest, richest coaching contract in hockey history.”

July 1: “Said buh-bye to Phil Kessel.”

July 23: “Convinced Lou Lamoriello to leave New Jersey after 28 years.”

It’s been a busy summer. And as for the season ahead? Who knows.

It’s Sunday afternoon and Shanahan is in his corner office at 50 Bay St., adjacent to the Air Canada Centre. If the appointment books and the perfectly organized desk give the air of a meticulous executive, it’s only one side of him. The rumpled t-shirt with the cartoon depictions of the cast of the original Star Trek and the un-coiffed hair falling over his forehead suggest there’s an ‘off’ switch in comfortable reach. But be clear: when it’s ‘on.’ not much gets in his way.

“I’m organized in some ways, not in others,” he says. “As a player I probably had some OCD. In things I care about I tend to get super driven. I say driven, my wife says obsessed.”

How obsessed? He tells a story about walking in Manhattan with his wife and over-hearing something about Muammar Gaddafi dying, turning to his wife and saying, out loud, “Gaddafi’s dead?”

“My wife is like, ‘you have to think about something other than your job.’ She says I should at least watch the Today Show, not the whole thing, just the first minute where they tell you a bomb dropped, or a hurricane is coming.’”

For the moment, he’s enjoying the calm before the storm in an empty weekend office, one he’s occupied for 18 months but only truly put his stamp on recently, his appointment book filling up with rapid-fire milestones. A year ago he still had coaches to fire and a scouting staff to turn over and star players to make judgements on.

Now?

“You feel more settled,” he says. “I had so many questions before last season. Some I had already answered in my head, but timing wise I had to wait on some things, but others were truly wait and see.”

On Wednesday night the Toronto Maple Leafs will host the Montreal Canadians in the NHL’s season opener and in some ways it represents base camp for the Shanahan-led Hockey Everest expedition: making the Leafs Stanley Cup champions for the first time in the Mimico kid’s lifetime, no small feat considering Shanahan will turn 47 later this season.

Last season, he says, was about evaluation. This season will be about progress, he says, however modest.

He’s not interested in looking back, just forward.

“There is a certain way they have to prepare and play in order to become the kind of organization and team that we want to be,” he says. “If that takes three months, three years, it doesn’t matter.

“It takes as long as it takes.”

Shanahan is aware that the plaudits he was getting all summer as he lured Babcock from Detroit and landed Lamoriello from New Jersey and pulled the trigger on trading Kessel to Pittsburgh won’t echo forever.

“It’s one thing to lay out a vision and a plan in the summer and everyone is patting you on the back and saying ‘go for it, we’re right with you,’ he says.

“I watch Game of Thrones and I know: ‘Winter’s coming, winter’s coming.’

“[But] People knew me as a player and who are starting to get to know me as an executive are starting to realize that – I don’t know if it’s three years of doing discipline at the league or my personality, but when I believe in something I don’t need to feel popular to carry it out.”

Unlike this time a year ago, however, when Shanahan’s most significant hire of the summer was fresh-faced Kyle Dubas, this winter and presumably for many more to come he’ll be able to ride out the storm with Babcock and Lamoriello as cornerstones and men who understand the price paid to win.

“All three of us have experienced it. Sometimes it’s a struggle right up until the moment someone hands you the Stanley Cup,” says Shanahan. “A real, difficult, angst-filled, unhappy struggle until the horn goes and you go ‘Holy F—, we just won the Cup, I can exhale.’”

He decided who he wanted to go to war with based on trust earned through personal experience, with Lamoriello in particular.

“When I was 19, I told him I wasn’t good enough for the NHL and he said ‘trust me Brendan, I know that you are’ and when I was and when I was 40 and told him I felt really good and I was good enough to keep playing he said ‘trust me Brendan, you’re not.’ Lou gave me life and death in the NHL.”

It’s a close relationship and it gave Shanahan both the confidence to approach Lamoriello about leaving the Devils and the belief that his style of leadership would set the tone for an organization trying to find it’s way.

“I knew a little more than just his persona and reputation that comes with him,” he says. “I think he’s the perfect fit, honestly, for where we are in our development, with management and with the players and the city and the stuff that I know is coming.”

It doesn’t mean a wholesale adoption of the rules and bylaws that Lamoriello famously instituted with the Devils, but certainly it will mean a more structured environment for what projects to be a young core in the coming years. The decision to reserve the Leafs charter for players and coaches only, meaning sponsors and broadcasters were no longer welcome, was a Lamoriello decision that Shanahan endorsed.

Others he’s pushed back on, but on the whole he feels it’s a framework badly needed a year removed from SaluteGate and Kessel’s media scrapes and Kadri’s never-defined suspension for being late to a team meeting.

“They’re simple little rules that might seem silly from the outside, but (Lamoriello) feels they are part of the discipline you need in order to feel there are lines [you can’t cross]. It seems like random rules, but to me it’s like a system on the ice. A system on the ice will make a player feel safe. Rules off the ice will also make the right player feel safe, that he’s obeying them and the others are too. The right players.”

Shanahan is expecting Babcock to provide that structure on ice, and again he relied on his own experience to be his guide before he backed up MLSE’s money truck and the sent the company plane.

“I had some good coaches along the way but in my 10th year in the NHL I played [in Detroit] for Scotty Bowman and he had a big reputation,” says Shanahan. “He was already in the Hall of Fame, but once you’re playing you don’t think about those things. But I remember at a certain point that season him making some adjustments, some decisions and some calls on the fly and it was the first time I remember being on a bench thinking our coach is better than yours, and that felt really good.”

“[And] I had Mike earlier in his career, for one year, and he has a lot of those attributes … early in that season in Detroit I remember starting to think the same thing.”

“We had a gap between Scotty and Mike [in Detroit] and we had Dave Lewis for a couple of years, and players are smart. They can hear when coaches are undecided. They can hear when coaches are unsure. They can hear them whispering behind them, ‘who do you think we should put on’ … those are all death signals, you know?

“And with your back to a guy for 82 games you know when someone is in charge and someone is good. There are a lot of good coaches in the NHL, I think [Babcock] is one of the best.”

Of course Shanahan has his own expectations too. While the Leafs determination to let their young players mature in the AHL could easily be interpreted as borrowing a page from Babcock’s ‘Red Wings Way,’ it’s actually something close to Shanahan’s heart, even if he never spent a single day in the minors in 22 NHL seasons.

Double standard?

The opposite, his own too-early introduction to the league involved a season-and-a-half of struggle that almost ended the No.2 overall pick’s career before it started.

“It didn’t work for me,” he says of jumping into the NHL as an 18-year-old. “It nearly ruined me. It took me a year-and-a-half [to get up to speed]. I couldn’t score, I couldn’t keep up. I played on the fourth line, so I just started fighting other fourth liners … it was getting embarrassing. I was reading stories about being a first-round bust.”

An injury opened up a spot on the top line and Shanahan thrived overnight. But the memory of being lost and out of his league early in his career sticks with him and it just might result in Connor Brown or William Nylander spending longer in the AHL than they would like.

“They probably don’t like the news they got [about not making the team out of training camp],” he says. “But they understand that we’re really interested in their career, not them getting their first game.”

Shanahan also expects playing for the Leafs to be considered a privilege, which could be a challenge given Babcock’s “There will be pain” mantra. From a distance he’s admired the work Toronto Blue Jays general manager Alex Anthopoulos has done in helping the Jays get to the post-season for the first time in 22 years, and has noted the kind of team he’s assembled, the way they play and how they’ve been embraced.

“You have to show that you enjoy playing in a city,” says Shanahan. “You’re performing in front of fans, they all want to be you. The one thing they want to see is that you appreciate being you and I think the Jays have captured that a little bit. They’re having fun doing it.”

But mostly, Shanahan expects to be successful. While his office and desktop give the impression of the unwaveringly focussed executive, he says that’s just one part of him. He’s not meticulously writing down plans, he’s recording dreams come true.

“People underestimate what imagination means and if you imagine something enough you get the confidence to think it’s actually real and make it happen,” he says. “Making the NHL, becoming a good player, doing the rules committee (during the NHL lockout) when I had no right to think I was the type of person to do that, doing this job. You have to imagine yourself doing it.”

In his active, vibrant mind, the same one that saw himself starring in the NHL when he was playing minor hockey in Mimico and saw himself hoisting a Stanley Cup when he was a struggling teenager, and now — perhaps most audaciously — as the architect of the great reconstruction at the ACC, he believes he’ll get there.

And when he does, he’ll be able to write it down in one of his plush appointment books.

Suggested heading? “This is how long it took.”