The former Islander volunteers as an assistant coach with the Long Island Royals, an under-16 hockey team coached by Hockey Hall-of-Famer Pat LaFontaine. A close friend and veteran of multiple triathlons, LaFontaine was happy to join Webb.
But he had a problem with the time commitment. A ride like that, which travels approximately 550 miles, usually encompasses up to nine days.
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What began as a laughable idea, though, is now a stark reality.
On Monday, LaFontaine and Webb will leave from the Hockey Hall of Fame in Toronto on a bike ride that will end a mere 48 hours later at the NHL Store in New York City.
The ambitious trip, which will raise awareness and money for LaFontaine and Webb's respective charities, as well as dementia and Alzheimer's research, has already drawn equal parts support and disbelief from former teammates.
"I just got off the phone with Brad Isbister. He says we're crazy," Webb told NHL.com. "Dave Scatchard is very supportive of the ride but still thinks we're crazy. Just about everybody we've talked to thinks we've gone off the rails. But we have a game plan and if we follow it properly, success should follow."
For Webb and LaFontaine, that game plan has been calculated down to the last calorie.
A team of about eight people will travel alongside them, helping to track caloric intake, heart rate, and other important variables. They'll even be playing music from an accompanying van. "I just hope Webby likes 70s music," joked LaFontaine. "If we have to listen to anything else, it could be a brawl out there."
With a live blog documenting their entire trip, the duo might seem an unlikely one considering how different the fleet-footed LaFontaine and tough-as-nails Webb were as players. It was actually LaFontaine who first got the former enforcer on a bicycle seven years ago, when he took Webb and then-Islanders defenseman Adrian Aucoin on a 100-mile "century ride." The results were mixed.
"Webby didn't bring the right nutrition. He didn't have breakfast, he thought 'this is going to be easy, I'm a hockey player.' He started getting really hungry about 60 miles in. I remember telling him, 'don't worry, the deli is just around the corner,'" said LaFontaine. "Then we get there and the deli is closed. You would have thought he was playing against the Rangers or something. He lost it, he just snapped."
Despite that bumpy first ride, Webb pursued bike riding full force and has embarked on a ride from Long Island to Peterborough, Ontario each of the past two summers. That ride, which generally takes between eight and nine days to complete, would form the basis for this project, which is raising funds for a number of causes, including both Webb and LaFontaine's personal charities.
LaFontaine's charity, Companions in Courage, has helped to build countless recreational areas, also known as "Lions Dens," in hospitals across North America. But following a tragic summer for the hockey world, Webb and LaFontaine have also decided to donate part of the funds raised to Alzheimer's and dementia research.
"There has been a lot of tragedy in our game. We'll honor those we've lost. That's something we'll be thinking about. I pray for the families and the children of those fathers. It's just tragic," said LaFontaine. "Obviously I have some strong feelings on head injuries, having gone through them myself."
It's definitely a departure from the daily NHL grind, but both men will draw on their considerable hockey experience as they embark on what should be their most draining adventure yet.
"I think sustaining your NHL career is similar to a long bike ride," said Webb. "It's not just about the start and it's not just about the finish. It's about the whole journey."