The undrafted free agent forward had to choose which NHL team to sign with, and Jason Botterill and Tom Fitzgerald convinced him to join Pittsburgh on an AHL-only deal.
Now, three years later, Sheary is a two-time Stanley Cup champion who just agreed to terms with the Penguins on a three-year, $9 million contract. The decision to join the Penguins was clearly the right one for the 25-year-old.
"My career has kind of been a whirlwind," Sheary admitted with a laugh. "Just going from three years ago, to think that I'd be signing this contract is something I never would have imagined. I was fortunate enough to pick the Penguins as the team I wanted to play for and they were obviously giving me every opportunity to prove myself, so I'm happy with that."
Sheary was also happy they were able to get the deal done before his arbitration hearing, which had been scheduled for Aug. 4.
"I'm very excited with the term and the contract that I got," Sheary said. "I was glad we were able to work it out before arbitration. I think it took maybe a little longer than I expected. It took a big chunk out of my summer. But I was glad to get it done because it was a little stressful thinking about it. it'll be nice to kind of sit back and enjoy the rest of the summer."
He said that his parents and sisters couldn't have been happier for him to get the process done.
"They were all excited," he said. "I think they kind of knew how stressful it was for me and what I was going through. I think they were probably relieved as well. They think it's a good contract. I've had many conversations with all of them and I think we're all just pretty happy to get the deal done and be in Pittsburgh again."
He added that while a one-year deal had been discussed, they ultimately decided three would be best.
"I liked the three-year term," he said. "We talked as well about a one-year term, but I think the three-year term worked out better for myself where I could have a little security and put a three-year body of work together where I can play hockey and not worry about a contract every year. I was very happy with that."
His deal came after teammates Brian Dumoulin and Justin Schultz signed their respective deals earlier in the summer, and Sheary said the three of them have been exchanging a lot of texts - and a few chirps.
"We're all pretty close friends," Sheary said. "We definitely have congratulated each other. We've said some inside jokes with each other about how much money Schultzy is making or whatever it may be. But it's all in good fun and I'm happy for those guys as well."
The team success has obviously been there for that group. Individually, Sheary wants to keep improving areas of his game he thought were weaknesses and continue doing whatever he can to help the team win.
"I want to stay consistent with my play and trying to improve on each year," he said. 'I don't want to have any slumps or anything like that. I want to make sure I prove myself year in and year out. Hopefully this year I can just keep improving and stay consistent throughout the year and hopefully we can have another good year as a team."
