He has previously played for the Columbus Blue Jackets, Philadelphia Flyers, Pittsburgh Penguins, and Vancouver Canucks in the National Hockey League (NHL).

In the 2014–15 season, with the role of enforcer declining in importance in the NHL, Sestito appeared sparingly in only 3 games with the Canucks before he was reassigned to their AHL affiliate, the Utica Comets.

[12] Though Sestito was technically a member of the Penguins' 2017 Stanley Cup winning squad, he was ultimately not permitted to hoist the trophy after being a healthy scratch for the entirety of the team's playoff run.

[14] On December 18, 2018, Sestito agreed to attempt a comeback, signing a professional tryout contract with the Toronto Marlies of the AHL, after he was approached by the club to add a physical presence.

[15] During his NHL career, Sestito was referred to as a "talentless thug"[16] and infamously as a "boxing hobo on skates" by ESPN commentator Keith Olbermann.

[17] While with the Canucks, Sestito made headlines after accumulating twenty-seven combined penalty minutes while officially receiving only one second of total ice time in a game against the Los Angeles Kings on January 13, 2014.

Sestito's teenage sister, Victoria, subsequently attacked Olbermann via Twitter, claiming that "the $7,268 for 1 second of work" was "probably just a little bit more than your liberal left wing ass makes."

[20] Canucks' General Manager Jim Benning stressed that his club needed players who could play in the opposition's end and contribute with more than an occasional fight.

[22] In late 2014, Sestito received criticism for tweeting that police were justified in the shooting death of an 18-year-old unarmed African American man named Michael Brown.