Auston Matthews knows about contract hell, and his negotiation with the Toronto Maple Leafs wasn't it.
"I went through a contract thing when I was going to Switzerland that was a debacle. Much more stressful than this," he said.
Matthews and his family made the decision to have him bring his talents to the Zurich Lions in 2015. It would be a year of professional seasoning for the consensus choice for first overall pick in the 2016 NHL draft. But the hoops he had to jump through to play there would have intimidated a Westminster show dog: earning "specialist status" to enter and work in the country, and then needing to take his GED exam to have graduated high school and be eligible for the season.
"It was an eight- or nine-hour test. Not a big school guy. My little sister is in high school now, and I look at her homework sometimes, and it absolutely looks like Chinese to me," he said with a laugh.
The immigration and academic issues of that contract made the negotiations on his blockbuster extension with the Maple Leafs seem quaint by comparison. "I wouldn't say [it's a] relief, it's just another step," Matthews said.
But it was a monumental step for the 21-year-old star center. Matthews signed a five-year $58.17 million contract on Feb. 5 that runs through 2024, for an $11.634 million average annual value. It's impossible not to trace the ripples around the NHL from this decision. It's as if someone dropped a boulder worth 14.6 percent of the current salary cap in the middle of a previously serene lake.
His contract affects the crop of restricted free agents this summer, both in their negotiations with their own teams and in the salary structures for potential offer-sheet poachers.
"We had to presume that with Connor [McDavid] being locked up, and with Auston as the next big deal, that it would have influence on the marketplace," Matthews' agent, Judd Moldaver, told ESPN this week. "So it's like Spider-Man: 'With great power comes great responsibility.' Ultimately, my job is his happiness, but there's no question his deal is going to be looked at [by other players]."
It affects Mitch Marner, his Leafs teammate and pending restricted free agent, whose contract will follow that of Matthews. "We don't talk about it much. It's not something that comes up much," said Matthews, who said he wasn't concerned that his decision would impact Marner's deal.
"When we do talk, it's not even hockey-related. It's a big thing in the media, but it's not something either of us stress too much in our minds. We just want to go out there and play hockey. We have agents for that stuff."
It obviously affects the Maple Leafs the most, because whatever contract Matthews signed would influence everything from their cap management to their personnel decisions. This is what made Matthews' negotiation different from that of McDavid's: The latter is an extraterrestrial talent whose team was going to pay him anything he asked to build around him, for he is the franchise; the Leafs, at least in the eyes of general manager Kyle Dubas and team president Brendan Shanahan, see Matthews as a franchise player but not as the franchise. Keeping him, and keeping him away from offer sheets, was vital. But it wouldn't come at the expense of the contender they were constructing.
The term that Matthews and his representatives -- agents Moldaver and Jeff Jackson of Wasserman (which also represents McDavid) as well as his father, Brian Matthews -- wanted was philosophically different from what the Leafs were determined to get.
"Of course, he coveted an eight-year term. He's committed to the Toronto Maple Leafs, and that would have been something he would have loved to have seen through," Moldaver said. "But we got to a point where, based on the complicated cap puzzle the Leafs have and in a hard-cap system, it became increasingly obvious that an eight-year term to serve his interests and the Leafs' interests just wasn't going to be right. And this was discussed amicably. Essentially, we looked at everything from three to eight years."
The three-year option was a nonstarter because that would have been too much risk for Matthews and too high an average annual value for the Leafs to cover that risk. The eight-year term would have also yielded a cap hit that was too high, as it would have gobbled up additional unrestricted free-agent seasons.
"This is just the nature of the way deals are in hockey. If you want the longer term, you're also taking out more of their prime. The AAV rises. Certainly, that was the intention from the beginning on Auston's side. They were focused on that," Dubas said. "We're trying to balance keeping this together with contending and not having to delete parts from it. We're very grateful they were willing to move off their desired term and maintain some flexibility."
So the term became five years. Matthews sold it as "a lot of guys have done five years before," which isn't necessarily accurate. Every first overall pick from 2008 through 2016 has signed a second contract of six or more seasons, save for two: Nail Yakupov, who is no longer in the NHL, and Steven Stamkos of the Tampa Bay Lightning, who signed a five-year deal worth 11.66 percent of the cap in 2011 before following it with an eight-year deal in 2016 to avoid free agency, worth 11.64 percent of the cap (a trajectory that Matthews seems to be on).
But here's the thing about first overall picks: Many of them are still on lousy or average teams after three seasons, which is to say that none of them signed their second contracts after their team signed the premier free agent on the market to a seven-year deal worth $77 million, as the Leafs did with John Tavares.
"Business trends change. Circumstances change. There are soon going to be 32 teams. Everyone has the same goal. But their business, the current status of their team -- if they're in a rebuild, if they're close to winning a championship -- and their marketplace influences how they run things," Moldaver said. "The Leafs have a puzzle, no doubt, [when] a superstar player in John Tavares signs as an unrestricted free agent."
So Dubas and the Leafs presented the puzzle thusly to Matthews: Five years keeps the team together with a window to win the Stanley Cup. That's where your piece fits best.
"We want to give ourselves the maximum number of chances we can to make a real good go at it," Dubas said.
Every good general manager understands his player's pressure points, and the one Matthews has isn't all that unique: He wants to win. Badly.
"In terms of the term, we considered everything. The Leafs were classy to deal with, but of course you're negotiating hard. Our job is to serve Auston's interest. He wanted a great deal, and our mandate was to give him as such. But the most important thing to him is that he wants to win. So his real only mandate was, 'Hey, let's do a great deal that helps the team as much as possible,'" Moldaver said. "As skilled as he is, I think Auston Matthews' greatest asset is his desire to win. Not to just talk about it, but to do it."
Could he have gotten eight years and still won in Toronto? "If Auston would have done an eight-year deal too, I don't think it would have decreased the chances of the team being successful, in a certain version of things. But in the reality of where they were at, it just made sense," Moldaver said.
There's no predicting if the Leafs will win the Stanley Cup within a six-year span -- this postseason and the next five years of Matthews' deal. There's really only one certainty after that: Matthews' contract will end with him facing unrestricted free agency in the summer of 2024.
Some pundits felt that term made this contract a loss for the Leafs. "I'm amazed that it's five years. I don't know how this makes sense for anybody in the management side. Five ... I want to know how they're going to keep him after five years," Brian Burke, former Maple Leafs general manager, said on Sportsnet. "If that's the price tag that he's got to buy one year of [unrestricted free agent] status, I don't know, given the tax structure in Ontario, how this guy stays one more day after five years. I really don't."
It has been noted that with this five-year contract, followed by a maximum eight-year deal, Matthews will make an incredible amount of money, while the Maple Leafs would be paying for his prime years rather than paying for ones after it, as they would have with two consecutive eight-year deals. The conspiratorial among us might wonder if this 13-year plan might be something the two sides discussed during these negotiations.
Both Moldaver and Dubas said there was no discussion at all about the next Matthews contract.
"It's our complete intention that Auston will spend his entire career with the Maple Leafs. The execution of that has two dimensions," Dubas said via email.
"First, we need to build our program in all regards into a consistently elite one, across all areas, in order to maximize our team potential and the potential of each individual athlete. Second, Auston needs to continue to do all he can to reach his potential on and off the ice as he has in his first 2.5 seasons. We have had no discussion at all about his next contract. We will enjoy the next number of seasons working together, rather than divert our attention to something so far in the future."
For Matthews, the contract talks are in the past. The terms are settled. He and his representatives feel it's a deal that's both beneficial to him and, ultimately, beneficial to him lifting the Stanley Cup in the near future for the Maple Leafs.
"In the end, you're measured on championships," Matthews said. "And that's what I want to bring to this team."