Rupp played high school hockey at St. Edward High School in Lakewood, Ohio and Team Ohio Midget AAA. He was originally drafted in the first round, ninth overall, by the New York Islanders in the 1998 NHL Entry Draft. After remaining unsigned while still playing in the Ontario Hockey League with the Erie Otters, however, Rupp opted to return to the NHL Entry Draft and was subsequently selected 76th overall in 2000 by the New Jersey Devils. Rupp played his first professional season in 2000–01 with the Albany River Rats of the American Hockey League, the top minor league affiliate of the Devils. He later made his NHL debut January 13, 2003 with the Devils, where he helped the team win the Stanley Cup after scoring the Cup-clinching goal. Rupp is the only player in Stanley Cup history to have his first playoff goal be the Stanley Cup winning goal. The following season, in 2003–04, Rupp was traded by the Devils, along with a second-round draft pick, to the Phoenix Coyotes in exchange for Jan Hrdina on March 5, 2004. After the 2004–05 NHL lockout, Rupp was traded with Jason Chimera and Cale Hulse to the Columbus Blue Jackets in exchange for Geoff Sanderson and Tim Jackman on October 8, 2005. Columbus declined to submit Rupp, a restricted free agent, a qualifying offer in June 2006. On July 9, 2006, Rupp signed a one-year, $450,000 contract to return to the New Jersey Devils. After a successful season establishing himself as a gritty hardworking player, Rupp re-signed with the Devils on June 28, 2007, to a two-year contract. On July 1, 2009, Rupp signed a two-year, $1.65 million contract with the Pittsburgh Penguins. While scoring his first career hat-trick on November 30, 2009, against the New York Rangers, Rupp scored his six, seventh and eighth goals for a new career-high just 28 games into the 2009–10 season. On July 1, 2011, Rupp signed a three-year, $4.5 million contract with the New York Rangers. He scored two goals in the 2012 Winter Classic against the Philadelphia Flyers to help the Rangers prevail 3–2. After Rupp scored his first goal, he saluted the crowd in a similar, yet mocking, fashion to how then-Flyer Jaromír Jágr celebrates a goal; the mocking gesture immediately led to a retaliatory confrontation initiated by Philadelphia forward Scott Hartnell. . . During the lockout-shortened, 48-game 2012–13 season, on February 4, 2013, Rupp was traded to the Minnesota Wild in exchange for forwards Darroll Powe and Nick Palmieri. On April 11, 2014, Rupp was suspended by the NHL for four games without pay for a "late illegal check to the head" of St. Louis Blues forward T. J. Oshie.
Broadcasting career
Since retiring in 2014, Rupp serves as both a studio analyst for the NHL Network, and a post-game analyst on Pittsburgh Penguins games for AT&T SportsNet Pittsburgh.
Personal life
Rupp's childhood ice hockey teams included the Parma Heights Wings Municipal Hockey Club, where he started playing at age nine. He attended and played for St. Edward High School, a catholic college preparatory school in Lakewood, Ohio. In just two years playing for the varsity squad at St. Edward, the team won two state championships in 1994 and 1995. After winning the Stanley Cup with the Devils, Rupp travelled to SouthPark Mall in Strongsville, Ohio, to display the Cup and sign autographs for fans in his home state. Rupp is a self professed Born Again Christian who became devoted to his faith after meeting his future wife Christi while playing in the OHL for the Erie Otters. The couple have four children together. Rupp serves as an assistant coach for the Erie Jr. Otters. Rupp was diagnosed with Wolff-Parkinson-White syndrome in 1998.
