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Like the error too that caught out Canadian Mike Douglas who was disqualified from the men's competition for removing his runner blade covers too late. Three minutes too late.
According to skeleton's rules, all runners for sleds have to be exposed to the air 45 minutes before competition.
"My good buddy and close friend and teammate Mike had a heart-wrenching day with his DQ at the start and my heart bleeds for him and his family," said Montgomery.
But he had to put that upset and Hollingsworth's finish out of his mind and focus on his own task at hand - bringing home gold.
"When you get to the line you're not thinking about anything but first of all the start and then the next inch in front of your nose as you go down the track," he said. You get beyond that, is when you get into trouble."
Friday night's drama, said Canada's assistant chef de mission Steve Podborski, was what got the crowd in motion.
"There's more Canadian flags up there and hoarse voices than I've seen in many a long year!" said Podborski, who was there to support Canada's athletes.
"It's really what makes sport so compelling," he said of Friday's competition.
"You know, for us it's a wonderful, joyful moment (to watch Montgomery win gold)."
But then there's the agony of Hollingsworth's day, he added.
"Here you have a bad moment, and your soul is right there.
"It can be very painful but it's pure."
Whistler's Jim Charters was at the event and was later walking through the village waving his big Canadian flag.
"What a wonderful thing. It's great to have something happen up here in Whistler," he said,
"Great for the community, great for Canada and good for him."