He was nine years old when they played in the 1993 playoffs and a teenager when Brendan Shanahan, from Clarkson's neighbourhood of Mimico, was traded to Detroit.
Now he has an up-close look after signing with his hometown Leafs.
"They're a team that's close by," Clarkson said of the Red Wings. "Any time you have an organization or a team that's close, you always have that playoff-type feeling."
It was the hope for HBO's "24/7" and the Winter Classic, that the Leafs and Red Wings would rekindle their old rivalry now that they're division rivals for the first time since 1998. But it will take more than just an internationally televised regular-season game to drudge up a lot of hostilities between Toronto and Detroit.
"Maybe the '24/7' and maybe the Winter Classic can help with all that," Red Wings coach Mike Babcock said. "To have a rivalry to me, what you do is you meet in the playoffs, you have two really good teams, you have hard series and you build up some animosity for one another. That hasn't been possible."
Forget about the playoffs. It hasn't been possible because until their Dec. 22 meeting at Air Canada Centre, the Leafs and Red Wings hadn't played a regular-season game against each other since Jan. 7, 2012.
Just over a dozen players remain from that meeting. Clarkson is one of the new participants, but he doesn't think the rivalry has deteriorated of late.
"I don't think from playing each other a ton over the last couple years, I don't think it's gone away," Clarkson said. "I think it's coming back. With them coming back and playing each other more, especially with (the Winter Classic) that's coming up, I think that rivalry's there and it's going to continue to grow and grow over the next couple of years."
Clarkson did his part to grow the hard feelings when he went after Red Wings forward Todd Bertuzzi during their game in Toronto.
"He shot the puck at our water bottle when it was on the ice, and I didn't like that," Clarkson said. "I just think that's part of the way both of us play, just kind of battling hard out there together."
That scene played out on "24/7," full of colourful language. It might've been the highlight of the show's third episode, which was supposed to showcase the rivalry going into Wednesday's game.
For television, that's all well and good. Leafs coach Randy Carlyle doesn't care about trying to manufacture a rivalry now that his team and the Red Wings are in the Atlantic Division together.
"I'm more concerned about winning hockey games than building a rivalry," Carlyle said. "I think when you ask every coach, the rivalry is something that develops when you have competitive teams and you play a number of times against one another.
"Obviously there's a long history between Toronto and Detroit, but with this coaching staff we're trying to make sure that we can provide a consistent brand of hockey, which we haven't been able to do."
The Leafs are 4-5-2 in their past 11 games, including a shootout victory over Detroit. The Red Wings are also 4-5-2 in that same span, going into their game Monday night at the Nashville Predators.
Nazem Kadri grew up a Leafs fan in London, Ont., about halfway between Toronto and Detroit. It was easier for his family to get tickets to Red Wings games growing up, so he went to see some games at Joe Louis Arena.
Now the Leafs' second-line centre, Kadri is also new to this rivalry but figures there's one way for the bad blood to heat up this season.
"Obviously Detroit being so close to us (in the standings) it definitely makes things a little more competitive," Kadri said.
Through Sunday's games, the Leafs and Red Wings were tied with 45 points and both sitting in wild-card positions in the Eastern Conference.
Daniel Alfredsson knows all about having a rivalry with the Leafs from his time with the Ottawa Senators. The Battle of Ontario got a spark with a 2004 playoff series, which might be what it takes for Toronto and Detroit.
"I think it's great that these two teams are in the same division now, and we're going to start to play each other a lot more," Alfredsson said. "But also I think you need to play each other in the playoffs to really create that heated rivalry as we had."
— Follow Stephen Whyno on Twitter at @SWhyno.
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