LAS VEGAS — Months of preparation have gone into a two-week period where the Toronto Maple Leafs are hoping to take a big step forward.
The front office may have been afforded more time than most to prepare for the draft and free agency, but that has upped the internal expectations with both now upon us.
This is one of the few times on the NHL calendar when an organization can contemplate seismic changes. Given where the Leafs have been, and where they want to be, it represents a rare opportunity to recalibrate the compass.
“We’ve tried to become almost over-prepared,” assistant general manager Kyle Dubas told Sportsnet on Monday. “It’s almost like preparing for a final exam: Try to do more than you humanly possibly think you can in terms of getting to know all of the players for the draft, all of the players for free agency. Trying to get an idea for the way things are going to break so that you’re not back on your feet when things start to happen.
"It's just game theory on a very public scale, in very rapid fashion. It's trying to study every single angle we can."
In addition to selecting fourth and 24th overall at Friday's draft, there is also the strong possibility for trades. Dubas noticed the chatter heat up immediately after the Stanley Cup was handed out last week.
"It just seemed that we were getting multiple calls every hour, people trying to test the waters and see what's happening," he said. "It's getting there."
Perhaps the most interesting aspect of the latest Maple Leafs makeover is that Dubas, the 28-year-old wunderkind, has been designated the point man. Responsibility is spread around in a front office without a full-time GM, but it's notable that agents and teams were told to contact him at the busiest time of year.
(Dubas will also represent the team for the first time at the GMs meeting here in Las Vegas on Tuesday.)
While he is no stranger to talking trade after running the OHL's Sault Ste. Marie Greyhounds for three seasons, the stakes are a little bit different now. When you have discussions involving Phil Kessel and Dion Phaneuf, for example, you're talking about players in the early stages of massive contracts.
Both players also hold limited no-trade clauses, as do teammates Joffrey Lupul and Tyler Bozak. Those complicate the process.
For obvious reasons, Dubas didn't delve into any specifics about ongoing negotiations when speaking with Sportsnet on Monday. However, he did mention that senior advisor Cliff Fletcher has been a good sounding board along with president Brendan Shanahan and coach Mike Babcock, and indicated the biggest difference between completing OHL and NHL trades is keeping things quiet.
"There's just a lot more paranoia about names getting out," said Dubas. "So we've tried to really keep everything closed off with our team as much as we possibly can. I think inevitably when you're talking about players with so many teams and then so many staffs are involved and so many agents are involved you're trying your best but it's going to go out there.
"We're trying to do things as privately as we can."
The one thing no one will argue is that there is a lot of work to do. In the short term the Leafs are focused on acquiring as many young assets as possible—be they in the form of draft picks or prospects brought in from other teams.
For example, it didn't take very long to cobble together a trade for Michigan winger Zach Hyman last week once the Florida Panthers called and made it known that they were willing to part with his rights.
"We've been working throughout the year, and then especially the last two months, to continue building our book on teams' prospect base and have a very select set of players from other teams that we want should any transactions come up," said Dubas.
The Leafs also expect to be active once free agency opens on July 1.
One of the fundamental principles the front office wants to establish is not rushing players—"We're not going to bring our younger guys up until they're absolutely 100 per cent ready to go up and stay; I'm referencing Connor Brown, William Nylander, Brendan Leipsic, Victor Loov on defence, Sam Carrick, all the way down," said Dubas—so next year's roster will need to be bolstered with veteran help from elsewhere.
They'll likely follow the blueprint established last summer, when depth forwards Daniel Winnik, Mike Santorelli and David Booth were brought in on one-year deals. Winnik and Santorelli were then flipped for other assets once the season went south.
In a free-agent class that is short on marquee names, Dubas believes Toronto will be a desirable destination.
"You can go back to the last couple years and see guys that have come in on one-(year) or short-term deals and parlayed that into a lot of visibility, a lot of good coverage and now they'll cash in here in July," he said. "So we'll be looking to do that. I think especially now with having Mike as our coach that how those types of players are viewed by the other teams will only improve.
"That'll be our key as we head into next week."
Brandon Pridham, the team's capologist, has taken a lead role on negotiations with restricted free agents Jonathan Bernier and Nazem Kadri.
Dubas is confident new deals will get done—"Both will be on our roster next year and key parts of our team"—and labelled the decision to file for team-elected salary arbitration on Bernier "a course of doing business-type thing"
"We want Jonathan in our net next year," he said. "That was a way for us to absolutely secure it."
These are heady times for Dubas, who was still working for the Greyhounds at this point last year. In fact, he pointed out that he'd never even spoken with Shanahan by then.
That happened shortly after he and wife, Shannon, were married in Mexico last July and his role as a NHL executive has only grown since.
"It's been a pretty crazy and amazing year on a personal level, getting married and then coming to the Leafs," said Dubas. "All of the different things that have happened with the Leafs this year, it's been crazy. I've learned a ton... It hasn't really overwhelmed me being in Toronto and doing this, but it's been a great year of experience and fun.
"I'm looking forward to this next week: Who knows what will happen?"
Another step forward for him. Ideally one for the organization, too.