Now, as McDavid skates toward being the top pick in the NHL draft, he lives by the idea that Bobby knows best. Orr is there to help him deal with the pressure of being hockey's "Next One" and anything else that comes up on or off the ice.
"I'm very lucky to have him around in my life," McDavid said. "He's been a great support guy for me that I can go to if I have any questions or any concerns. He's been through it all, he's done anything that a hockey player wants to do. He's done it all. If there's one guy you can go to talk to, he's a pretty darn good guy to go to."
McDavid isn't the first prospect to lean on Orr. He's the agent for past No. 1 picks Taylor Hall and Aaron Ekblad, and the Orr Hockey Group represents over 30 NHL players.
Orr knows McDavid is a kind of unique talent who "comes along once in a while," so his role is even more heightened this time. With all the pressure and expectations on the shoulders of an 18-year-old, Orr just wants McDavid to keep loving hockey.
"The big thing with Connor and any of the young kids: Don't ever lose the love and passion for the game," Orr said Thursday at the CHL prospects game, where he's coaching McDavid. "This game can be a job. I never looked at it as a job, I loved to go to practice, I loved to play. ...
"What Connor's gone through the last few years, it really is incredible how stable he has stayed. A lot of that has to do with his family, too. That's the thing: Some kids get the kind of pressure put on them, they just lose that love and passion for the game."
That doesn't sound like a problem for McDavid, who never seems to take playing hockey for granted.
"I love the game so much and I work hard at it and I have a lot of fun with it," he said. "There's something about playing in junior and being with your buddies all the time and going through that run, it's hard not to fall in love with it."
McDavid, who's in his third season with the Erie Otters of the Ontario Hockey League, doesn't see Orr often. But the two speak on the phone and text message each other to stay in touch.
That's a typical player-agent relationship, but for McDavid, it's even more special. Consider the source.
"When Bobby Orr talks, you're listening," McDavid said. "You're making sure that you're doing what he says. If you want success, he's a great guy to kind of follow."
Don Cherry, a friend of Orr's dating to his time coaching the Hall of Fame defenceman on the Boston Bruins, sees an off-ice benefit for McDavid in this relationship.
"I think with all the publicity, this is how you handle it," said Cherry, the other coach in the CHL prospects game. "The PR and stuff like that, Bobby can help him that way, among many other things. Being a celebrity and how to handle it."
McDavid has been in the limelight for a few years already and handles the attention about as well as anyone that age can. Surrounded by a handful of reporters and cameras Thursday, the Newmarket, Ont., native brushed the attention off as easy compared to the hoopla of the world juniors.
The best advice that Orr gives McDavid is almost fatherly. It doesn't hurt to come from the greatest defenceman to play the sport, but it's not too hockey-specific.
"He's just checking up on me, making sure that I'm doing all the right stuff, always reminding me to sleep more and get my rest," McDavid said. "As a teenager you've got a lot of stuff going on all the time. It's hard to find a couple extra hours of sleep. He's always reminding me and making sure I'm doing that."
Orr said the same thing to Ekblad, and probably Hall before that. The 66-year-old believes kids don't rest these days and preaches that it's very important.
"He wants to be on the ice," Orr said of McDavid. "He has a love and passion for this game, and that's where he's the happiest."
Having McDavid on the ice next season is going to make one NHL team very happy. There's a reason a few of the league's worst teams are willing to slip to the bottom of the standings this year in order to increase their odds of getting McDavid.
Asked if he thought McDavid would make an immediate impact as a professional, Orr said he knew it would happen at some point but didn't want to guarantee when. As much skill as McDavid has, there's work he must do before moving to the next level.
"He knows to play in the NHL next year he's got to get stronger," Orr said. "He doesn't put himself in positions a lot to have to battle too much. He plays kind of a different game, but he has to get stronger like all these kids."
Physical strength will come with another summer in the gym and time as McDavid grows. As for mental strength and commitment to hockey, that has grown the more he plays.
"If you're starting to lose the love of the game, it means you're not going to work as hard," McDavid said. "You're playing the game that you fell in love with as a kid, and now I guess you're just doing it on a bigger stage."
This time next year, McDavid will be on the biggest of stages in the NHL. And Orr isn't worried about him not being ready on a personal level for that challenge.
"Not only is he a wonderful player, he's a wonderful young man," Orr said. "He's going to represent our game so well for a long, long time."
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