A left shot who can play on either side, the 5-foot-8, 175-pound Sheary is a swift-skating winger who is strong on the forecheck and isn't shy about shooting the puck. He has been fairly durable for his size and has been occasionally deployed on the second power play unit. He will likely be in the mix for a third- or fourth-line role in Washington.
Sheary becomes the third former Penguin to migrate to Washington this year; he follows forward Daniel Sprong (obtained in a Feb. trade with Anaheim) and defenseman Justin Schultz (signed as a free agent in Oct.). Both Sheary and Schultz were members of the Penguins' back-to-back Stanley Cup championship squads in 2015-16 and 2016-17.
The 28-year-old Sheary played four seasons of collegiate hockey at UMass (Amherst), signing an amateur tryout agreement with AHL Wilkes-Barre/Scranton at the conclusion of his senior year. He got into two regular season games with the Baby Pens at the tail end of that 2013-14 season, but really opened eyes with six goals and 11 points in 15 Calder Cup playoff games that spring.
Sheary signed a free agent deal with WBS for the 2014-15 season, posting 20 goals and 45 points in 58 regular season contests, and adding five goals and a dozen points in just eight playoff games. This performance in his first full pro season earned him his first NHL contract; the Penguins signed him on July 1, 2015.
After starting the '15-16 season in the AHL, Sheary was promoted to Pittsburgh where he made his NHL debut in Boston on Dec. 16, 2015 (four days after Pens Mike Sullivan was promoted from WBS to Pittsburgh as Pens head coach) in his home state of Massachusetts. Two nights later in Pittsburgh, he notched his first NHL goal against the Bruins' Tuukka Rask, adding an assist.
Sheary totaled seven goals and 10 points in 44 games with the Pens in his first taste of NHL action, averaging just under 10 minutes a night. He added four goals and 10 points in 23 playoff contests, helping the Pens to the first of their two consecutive Cup titles. The last of those four playoff goals was an overtime game-winner in Game 2 of the Stanley Cup Final against San Jose on June 1, 2016, the first overtime game-winner by a rookie in the Cup Final in 30 years.
Sheary broke out with a 23-goal, 53-point season in just 61 games as a sophomore in 2016-17, his first full NHL campaign. He netted 21 of those goals at even strength, adding two goals and seven points in 22 playoff games.
Since peaking at 23 goals with the Pens in 2016-17, Sheary has seen his scoring totals decline each year. Playing a career high 79 games in 2017-18, he finished with 18 goals and 30 points. At season's end, he was shuffled off to Buffalo along with blueliner Matt Hunwick in exchange for a fourth-rounder in the 2019 NHL Draft.
With the Sabres, Sheary totaled 14 goals and 34 points in 78 games in 2018-19. Last season, he had nine goals and 19 points in 55 games with Buffalo before being returned to the Pens in a deadline deal for Dominik Kahun. Sheary had a goal and four points in an eight-game stint with Pittsburgh before the pandemic hit, and he collected two assists in four playoff games with the Penguins last summer.
Over the course of his five-season NHL career, Sheary has totaled 72 goals and 150 points in 325 regular season games, adding six goals and 21 points in 61 Stanley Cup playoff contests.
