Career
He is currently playing with the Binghamton Senators of the American Hockey League (AHL) as a prospect for the Ottawa Senators of the National Hockey League (National Hockey League). Rupert was selected by the Toronto Maple Leafs in the 6th round (157th overall) of the 2012 National Hockey League Entry Draft. Rupert played major junior hockey with the London Knights of the Ontario Hockey League (OHL), earning 58 goals, 136 assists, and 279 penalty minutes, in 224 career games with the Knights.
He helped his team to capture the J. Ross Robertson Cup as league champions for both the 2011-2012 and 2012-2013 OHL seasons.
On April 10, 2014, the Toronto Maple Leafs signed Rupert to a three-year, entry-level contract. In the 2015-2016 season, and in the midst of his second professional year within the Leafs organization, on February 9, 2016, Rupert was included in a blockbuster nine-player deal that focused around Dion Phaneuf moving to the Ottawa Senators.
