TORONTO – John Tavares is leaping into the great unknown.

The biggest free agent of the NHL’s salary cap era has decided to pass up more security, more money, more tax breaks and more sunny days in January. He’s taking the road less travelled to come home and help the Toronto Maple Leafs try to end a Stanley Cup drought that spans generations.

Talk about a stunner.

There was considerable skepticism inside the hockey industry that Tavares would ever test the open market after spending nine seasons with the New York Islanders. Even as the possibility grew in recent days, many identified the San Jose Sharks as the front-runner for his services.

And yet there Tavares was ringing in a life-changing Canada Day by signing a $77-million, seven-year deal with the Maple Leafs instead.

It says a lot about how far the organization has come that they emerged as the successful bidder at the end of a thorough, heart-wrenching courting process. Tavares had his pick of the litter. He could have played anywhere he wanted and been paid a fortune to do so.

Toronto offers him the chance to live close to friends and family and cement a legacy that couldn’t be had anywhere else. It’s been 51 years since the city hosted a Stanley Cup parade. Imagine if a 27-year-old born in Mississauga and raised in Oakville – a man who was once a child star for the Toronto Marlboros in the GTHL – managed to change that by joining a promising young core and pushing them over the top?

The allure was simply too much for Tavares to pass up.

He and his agents at CAA Sports were blown away by the presentation the Leafs made earlier this week at their Beverly Hills headquarters. Team president Brendan Shanahan, general manager Kyle Dubas and head coach Mike Babcock were all in the room and Dubas, in particular, made a huge impression with his confident, well-articulated delivery while outlining the organization’s plans.

They were the first of six teams to make a pitch – followed by the Islanders, Sharks, Bruins, Stars and Lightning – and emerged victorious after Tavares returned to his off-season home in Toronto for three days of soul-searching and reflection.

It was a difficult, emotional process for a guy taken first overall by the Islanders in 2009. This sport doesn’t have any history of players with his stature choosing to walk out the door in the prime of their career. New York pushed hard to retain him – new GM Lou Lamoriello had dinner with Tavares and agent Pat Brisson before taking the job in May and maintained an active dialogue right up until the end – but the star centre couldn’t ignore the fact he’d have a better opportunity to win with any of the other teams in his final six.

That resonated deeply with Tavares, who appeared in just 24 playoff games with the Islanders. His tenure with that organization is a story of missed opportunity – one that saw management consistently fail to put a strong enough team around him, including, perplexingly, last season while he played out the final year of his contract and inched closer to free agency.

Facing another playoff-less spring, Tavares spent the last two months preparing for the biggest decision of his professional life. It included numerous meetings and conversations and saw his agents prepare a 77-page booklet that included a deep dive on every organization with a serious shot at landing him.

They left no stone unturned.

An enticing part of the Leafs pitch to Tavares was that he’d be given the opportunity to play with Mitch Marner, according to sources, which is a not-insignificant fact when you consider he’s ninth in points per game league-wide since 2012 despite never having a winger anywhere close to that calibre. He helped make a lot of money for guys like Matt Moulson and P-A Parenteau over the years.

Tavares was also lobbied in recent days by Auston Matthews, the 20-year-old Leafs Alpha dog who was among the players to reach out to him directly during his free-agent window. Those close to Matthews say he’s thrilled to welcome another star to Toronto and isn’t worried about how it might impact his ice time or whether he’s granted the captaincy because he wants to win a championship and believes that he and Tavares can accomplish “special things” together.

Clearly, the feeling is mutual.

What is perhaps most surprising is that Tavares is electing to jump back into the fishbowl at a time when he could have instead chosen the quiet life. The opportunity to chase the Stanley Cup is just as good in San Jose and Tampa, for example, and he would have been afforded a more warm, laid-back environment to do it.

However, it is in a quote from his draft night where we can gain a better understanding about how he’s ended up here now. Back in June 2009 at the Bell Centre, Tavares told reporters: “I’ve got a great passion and heart for the game, and I’m very determined and focused on where I want to be and what I want to be.”

This is a guy who wants to win Stanley Cups and play his way into the Hockey Hall of Fame – not toil away in mediocrity, or anonymity, on the path of least resistance. Remember that he once gained entrance to the Ontario Hockey League a year earlier than everyone else and immediately scored 45 goals in 65 games for the Oshawa Generals.

And so at the start of a life-altering summer where he’s due to be married, Tavares carefully surveyed his options and couldn’t shake the idea that a hockey career is short and the chance to do something this special might never be in his grasp again.