Conor Sheary Siblings: All About Caitlin and Courtney Sheary

Conor Sheary is an American professional ice hockey winger for the New York Rangers of the National Hockey League (NHL).

Born on June 8, 1992, in Winchester, Massachusetts, he grew up in Melrose, Massachusetts.

The left-shooting forward is known for his speed, hockey sense, and ability to produce offense in a bottom-six or complementary role.

Undrafted out of the University of Massachusetts Amherst, Sheary signed with the Pittsburgh Penguins as a free agent and quickly made an impact, becoming a two-time Stanley Cup champion early in his career.

He has played for several NHL teams, including the Penguins (twice), Buffalo Sabres, Washington Capitals, Tampa Bay Lightning, and now the Rangers, bringing veteran reliability and playoff experience.

Siblings

Conor grew up in a close-knit family in Melrose, Massachusetts, with his parents Kevin and Robin Sheary and his two older sisters, Caitlin and Courtney.

His sister Courtney played college hockey at the University of New Hampshire, while Caitlin also influenced his path and graduated from UMass.

Conor has credited his sisters, particularly the oldest one who played hockey, with inspiring him and pushing him to improve from a young age.

Also Read: Mika Zibanejad Siblings: Get to Know Monir Kalgoum

Career

Sheary excelled at Cushing Academy before committing to the University of Massachusetts Amherst, where he developed into a productive scorer and served as team captain in his senior year.

After going undrafted, he turned pro with the Wilkes-Barre/Scranton Penguins of the AHL and impressed enough to earn an NHL contract with Pittsburgh.

He made his NHL debut in December 2015 and quickly earned a regular role, playing alongside stars like Sidney Crosby.

Sheary contributed meaningfully during the Penguins’ back-to-back Stanley Cup runs in 2016 and 2017, including scoring an overtime winner in the 2016 Finals.

After a strong 53-point season in 2016-17, he was traded to the Buffalo Sabres in 2018, where he played top-nine minutes.

He returned briefly to Pittsburgh before signing with the Washington Capitals, enjoying productive seasons there as a consistent point producer.

A three-year deal with the Tampa Bay Lightning followed in 2023, though his role diminished later, leading to AHL time with Syracuse.

In 2025, he signed with the New York Rangers, adding veteran depth to their forward group.

Over his career, Sheary has appeared in more than 650 NHL games, known for his work ethic and clutch playoff performances.

Accolades

Sheary’s most notable achievements are his two Stanley Cup championships with the Pittsburgh Penguins in 2016 and 2017.

He scored key goals in the playoffs, including an overtime game-winner in the 2016 Stanley Cup Final.

At the college level, he was a captain and one of UMass’s all-time leading scorers.

While he has not won major individual NHL awards, Sheary has earned recognition for his perseverance as an undrafted player who reached the highest levels of the game and contributed to championship teams.