Fast-forward to Thursday afternoon in Edmonton and things have changed quite a bit. These days it's Jake DeBrusk, now in his second season with the Black & Gold, who is making his mark on the NHL, while his father - retired since 2004 - works as an analyst on the Oilers' television broadcast.
But one thing remains the same since those days in the late '90s: Chara, now 41, is still one of the NHL's most respected - and effective - defensemen.
"It's impressive. I think that's probably the biggest thing I take away from him is just his work ethic, off and on the ice," said Jake DeBrusk. "He's always in the gym. He's one of the first guys in there and one of the last guys out. I think it's just kind of how he prepares for games. He has a set routine, and as a young guy I just try to take as much as I can from him because he's been in the league as long as I've been around.
"Just saying that is impressive. How the game has changed, nowadays the speed of it - for him to be able to adjust, especially at his size, it's very impressive and it's something that we all try to be like."
Chara's longevity is truly something to behold and on occasions like Thursday night it's also something to appreciate. When the Bruins captain takes the ice against the Oilers, it will mark his 900th game with Boston, making him just the sixth player in franchise history to achieve that feat, joining Ray Bourque (1,518), Johnny Bucyk (1,436), Don Sweeney (1,052), Wayne Cashman (1,027), and Patrice Bergeron (969).
"Definitely appreciate it and it's a huge honor, it's a privilege," said Chara, who is in the midst of his 13th season with the Bruins. "It's been, obviously, quite some time, but I've been very proud of being part of this organization and very thankful to have owners like we have; they make it very convenient for me and my family to stay in this organization, in Boston, for as long as we have. It's been great and I'm very thankful."