The "brothers" - who have a group Snapchat named "The Billet Brothers" - have been inseparable. Khenan and Craig attended all of Jarry's games with the Oil Kings - watching him win a Western Hockey League title and Memorial Cup - and made trips to watch him in Wilkes-Barre/Scranton.
But during the Penguins' western Canadian road trip, the entire family had a chance to watching Jarry practice at Rogers Place and then defeat the Edmonton Oilers the following evening.
"It's cool to see his development from juniors to the American Hockey League to the NHL," Khenan said. "We went down to Wilkes-Barre a few times to watch him and see some practices. We got to see his practice (in Edmonton).
"It's really cool to see him live his dream out in the NHL."
Though Jarry has a reserved personality - "I don't really speak too much. I just keep quiet, keep to myself" - underneath hides a confident and aspirational young man. Even in his youth, Jarry believed that he would make it to hockey's highest level.
"I remember when he was young playing in juniors we talked about him playing in the NHL," Craig said. "He said, 'Boys, I'm going to make it.' Seeing him now, especially the way he's been playing, is insane."
The family always knew Jarry had what it takes to make it to the big show, but watching him take on the Oilers in person in late December was still a surreal experience.
"I still can't quite believe it, frankly," Ernie admitted. "People that I work with are always going, 'He lived with you?!'
"It's been an exciting run. We always knew he had the talent, but the NHL level is a lot different than the junior level. We've always been there to cheer him on."
And the family is elated to see how far Jarry has come from those early puppy days, maturing into a man living out his dream in the NHL.
"He's made a lot of sacrifices being a junior player, the stuff these guys miss out on as young men," Lori said. "Now it's all paying off for him. I think that's the best part of the whole thing. That's why I'm so proud of him."