The Total Tutor Neil Haley will interview Back to Back Stanley Cup Champion Conor Sheary Live From Macys. In addiiton, Neil will interview selected fans from the event.

On March 13, 2016, Sheary recorded his first multi-goal game, scoring 2 goals against the New York Rangers at MSG against goaltender Henrik Lundqvist. He would then record his first career playoff goal vs Lundqvist on April 21, 2016. On June 1, 2016, Sheary scored the game-winner, in overtime, to win against the San Jose Sharks 2–1 in the Stanley Cup Finals. On June 12, 2016, Sheary won the Stanley Cup with the Pittsburgh Penguins in a 3–1 victory against the San Jose Sharks.

In the 2016-17 NHL Season, Sheary continued to play alongside Sidney Crosby for the entire year, getting 23 goals and 30 assists for 53 points. Sheary got his first 3-point game on January 16, 2017, against the Washington Capitals. The Penguins won the game 8–7 in overtime, with Sheary scoring the overtime winner.