Players considered undersized constantly look for the right opportunity to prove themselves. Sheary found that chance with the Penguins and proved to be an integral piece of the 2016 Stanley Cup championship season.

Sheary played high school hockey at Cushing Academy in Ashburnham, Mass., which has also produced NHL players such as Keith Yandle and Zach Bogosian. But at 5-foot-8 and 175 pounds, Sheary was passed over in the NHL Draft, so he headed to the University of Massachusetts-Amherst.

Sheary had a solid four-year college career, with 38 goals and 104 points in 138 games. He was UMass' captain during his senior season in 2013-14, when he led the team with 28 points in 34 games.

After college, Sheary immediately joined Wilkes-Barre/Scranton of the American Hockey League on a tryout contract and appeared in the final two games of the regular season before showing his potential in the postseason with six goals and 11 points in 15 games. He remained with Wilkes-Barre/Scranton for the 2014-15 season on an AHL contract and finished with 20 goals and 45 points in 58 games.

Sheary signed a two-year, entry-level contract with Pittsburgh on July 1, 2015. After starting the season in the AHL with seven goals and 36 points in 30 games, he was called up to the Penguins on Dec. 15, 2015, joining head coach Mike Sullivan, who had started the season as head coach of Wilkes-Barre/Scranton before being promoted on Dec. 12.

Sheary had his first career goal and assist in his second game (a 6-2 loss to the Boston Bruins on Dec. 18, 2015) and eventually landed in a top-line role playing wing alongside Pittsburgh captain Sidney Crosby for a good portion of the second half of the season.

Though he finished his rookie season with seven goals and 10 points in 44 games, he matched that point total in the postseason, scoring four goals. Sheary scored twice in the Stanley Cup Final against the San Jose Sharks, including the winning goal in overtime in Game 2.