Rychel, who was 14 and 15 then, saw up close what he would be playing for in the next four years, what it would take to get it and how it would feel to win it.
Kerby is now in a position to lift that Cup because his father traded him to the Guelph Storm in December. Warren Rychel, who played 406 NHL games for Los Angeles, Colorado, Anaheim and Toronto, has been the Spitfires co-owner and general manager since 2006.
Kerby's trade was a moment of life reflecting art, or life reflecting a television commercial.
Tampa Bay Lightning forward Steve Stamkos and Jordan Eberle of the Edmonton Oilers acted this past season in a soft-drink commercial. Stamkos portrays a player who is traded by his father for Eberle.
Kerby Rychel wasn't as stunned as Stamkos was directed to be. Kerby wasn't even surprised even though he was Windsor's captain. He'd had a front-row seat on the business of running a hockey team.
The Spitfires were decent, but didn't have all the pieces for a run to the top of a tough Western Conference in the Ontario Hockey League. Kerby was the kind of asset that could be parlayed into multiple future assets, which Windsor desperately needed.
The OHL had fined Windsor $400,000 in the summer of 2012 and also stripped the Spitfires of three future first-round draft picks and a pair of second rounders for "unspecified recruitment violations."
"I kind of knew I was going to get traded," Kerby said. "I kind of just knew with it me being my last year and all the sanctions the Spitfires had. They didn't have too many assets to upgrade. It's part of the business and it kind of worked out for both teams.
"They can rebuild now and I think they're going to be a force to be reckoned with in the upcoming years."
For eight draft picks and an 18-year-old winger, Guelph received Kerby, a first-round pick of the Columbus Blue Jackets, and fourth-year defenceman Nick Ebert, a Los Angeles Kings prospect.
It wasn't the first instance of a high-profile hockey father trading his son in 2013. Former Toronto Maple Leaf and current Kingston Frontenacs GM Doug Gilmour dealt Jake to the Niagara IceDogs last summer.
Warren made a trade to get both his son and Ebert from Mississauga midway through their rookie OHL seasons. It was a straightforward meeting between father and son when Kerby was dealt to the Storm.
"He brought me into his office and said, 'We've traded you to Guelph and it's a good opportunity for you. This being your last year in the league, it gives you a good opportunity to win,'" Kerby recalled.
"We kind of did a good job throughout my time in Windsor to keep the player and GM hat on. From Day 1, we had a talk and said he's my dad away from the rink and he's my GM at the rink. We definitely made it work. Players respected me in the room and no one looked at me differently, special treatment or anything like that."
Kerby Rychel's arrival enhanced a Guelph offence that already boasted multiple offensive weapons. The Storm were the highest-scoring team in the Canadian Hockey League — the umbrella league of the Western, Ontario and Quebec leagues — with 340 goals.
At six foot one and 205 pounds, Kerby is a combination of skill and muscle. The 19-year-old from Tecumseh, Ont., played for Canada at this year's world junior championship and posted 90 points in 58 regular-season games.
He led the OHL in playoff points with 11 goals and 21 assists in 20 games.
In the OHL championship series against North Bay, Kerby scored twice in the final 30 seconds of Game 5 to clinch the win and book a trip to the Memorial Cup.
He also scored Guelph's first two goals of the Memorial Cup in a 5-2 win over the Edmonton Oil Kings.
"I didn't only get brought here to score goals," Kerby said. "They have a lot of guys who can do that. I like to think I can play a well-rounded game, play hard and do some of that dirty work you can call it.
"It probably is my last year and to win a Memorial Cup is one of the hardest trophies in sports to win. It would definitely be a really special moment for sure."
Storm head coach Scott Walker, a former NHL defenceman with Vancouver, Nashville and Carolina, played against Warren Rychel during their careers.
"Warren was a competitor and I think you see that in Kerby," Walker said. "Block shots, take hits, give hits at all costs."
Kerby is one of several players at the 2014 MasterCard Memorial Cup with close family ties to the NHL. Guelph's Brock McGinn is the brother of Colorado Avalanche forward Jamie McGinn and Tyler Bertuzzi is the nephew of Detroit Red Wings Todd Bertuzzi.
On the Edmonton Oil Kings, defenceman and captain Griffin Reinhart is the son of former Calgary Flames defenceman Paul Reinhart. Forward Henrik Samuelsson is the son of NHL veteran Ulf Samuelsson, who is now an assistant coach of the New York Rangers. Mads Eller is the younger sibling of Montreal Canadiens forward Lars Eller.
Former Maple Leaf Tie Domi's son Max is a London Knights left-winger. Val-d'Or Foreurs top scorer Anthony Mantha is the grandson of Andre Pronovost who played 11 seasons with Montreal, Detroit and Boston.
"It's definitely an advantage to have and they can teach you a lot of things," Kerby said. "You can always turn to them for advice."