The first baseman from Mississauga, Ont., drove the ball into the second deck behind right-centre field at Target Field for his first homer of the high-school level competition.
"I just got my head on that baseball and my barrel got through the zone," said Naylor. "I felt really good on that one."
Despite the strong start Naylor eventually lost 7-4 to Luken Baker, a catcher/right-handed pitcher from Conroe, Tex.
"It was a little nerve-racking at first but I got through it after my first home run," said Naylor. "It was just amazing hitting in front of everyone, all the big leaguers, all the fans."
Naylor and Baker went to bat during the television commercial breaks of MLB's home run derby, keeping the sold-out crowd entertained. It also gave Naylor a chance to solicit advice from the major league players on the field, including fellow Canadian Justin Morneau, a first baseman with the Colorado Rockies.
Morneau, from New Westminster, B.C., won MLB's home run derby in 2008.
"We just discussed how I should go about taking swings, how patient I should be," said Naylor. "I asked him how the derby went in 2008 and what his mentality was when he went in it.
"I asked him tonight how many he was going to hit and he said 'I'm just going to start with one and work my way up.'"
Morneau, who used to play for the Twins, received a standing ovation from the Minnesota crowd when he was introduced before the competition. He hit two home runs in the first round of the National League bracket and was eliminated by eventual finalist Todd Frazier of the Cincinnati Reds in a tie-breaker round.
The Oakland Athletics' Yoenis Cespedes was the winner of the MLB home run derby.
Naylor was just appreciative of the opportunity to compete.
"You're never going to get this experience again," said Naylor. "Hopefully it comes again, but this is rare for some people. I'm blessed to be in this situation right now, to be here and to be experiencing everything I am. I got to hang out with major leaguers today and I talked to a few of them, took pictures with a lot of them. I even saw them hit. You don't get to do that every day.
"Just be thankful for every opportunity."
— By John Chidley-Hill in Toronto