Players considered undersized constantly look for the right opportunity to prove themselves. Sheary found that chance with the Pittsburgh 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, Massachusetts, 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 collegiate career, with 104 points (38 goals, 66 assists) in 138 games. He was UMass' captain during his senior season in 2013-14, when he led the team with 28 points (nine goals, 19 assists) in 34 games.

Sheary 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 45 points (20 goals, 25 assists) in 58 games.

Sheary signed a two-year, entry-level contract with the Penguins on July 1, 2015. After starting the season in the AHL with 36 points (seven goals, 29 assists) 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 Dec. 12.

Sheary made his NHL debut Dec. 16, 2015, against the Boston Bruins, and had his first NHL goal and assist in his second game two nights later, also against the Bruins. He eventually landed in a top-line role playing wing alongside Sidney Crosby for a good portion of the second half of the season.

Sheary finished his rookie season with seven goals and 10 points in 44 games, and matched that point total in the postseason, scoring four goals in 23 games. Sheary scored twice in the 2016 Stanley Cup Final against the San Jose Sharks, including the winning goal in overtime in Game 2.

Sheary scored an NHL career-high 53 points (23 goals, 30 assists) in 61 games in 2016-17 and had seven points (two goals, five assists) in 22 playoff games to help the Penguins win a second straight Stanley Cup.

NOTES & TRANSACTIONS

• Signed as a free agent by Pittsburgh, July 1, 2015.
• Traded to Buffalo by Pittsburgh with Matt Hunwick for a conditional pick in 2019 NHL Draft, June 27, 2018.
• Traded to Pittsburgh by Buffalo with Evan Rodrigues for Dominik Kahun, February 24, 2020.
• Signed as a free agent by Washington, Dec. 22, 2020.