There is nothing like having a familiar face when transitioning to new surroundings. Mike Sullivan made sure to sign a two-time Stanley Cup champion he coached before, for his debut with the New York Rangers in the 2025-26 NHL season. As Sidney Crosby and the Pittsburgh Penguins visit The Big Apple, they might face a former teammate.

After a deflating 2024-25 NHL campaign, former teammate of Crosby in Pittsburgh, Conor Sheary wants to showcase his worth in the city where dreams are made. He definitely passed the eye-test during his professional tryout (PTO) with Sullivan’s Rangers, as he is earned himself a contract.

“Conor Sheary signs a one-year deal with the New York Rangers, converting his PTO into a job,” as stated by insider Chris Johnston on X (formerly Twitter).

Bare minimum

Sullivan and the Rangers signed Sheary to a league minimum deal at one-year, $775,000. While far from breaking the piggy bank, the deal gives Sheary a chance to redeem himself after spending most of last season in the AHL.

Conor Sheary hoists the Stanley Cup

After appearing in 57 games during the 2023–24 campaign with the Tampa Bay Lightning, Sheary played just five NHL outings the following season. However, reuniting with Sullivan—who coached him and Crosby to back-to-back Stanley Cups in Pittsburgh—might be just what the 33-year-old needs to revive his career in the majors.

All the emotions

Sheary signed a two-way contract, meaning he can be moved up and down the organization throughout the season. Most likely, he will start with the AHL’s Hartford Wolf Pack but could occasionally make his way onto the NHL lineup.

Being on the ice at Madison Square Garden for the season opener against the Penguins would have been a very special moment for Sheary—his first league appearance since February 6 and only his second in 2025—facing many familiar faces on the visiting team’s bench.