Despite excelling in the minors, York found it difficult to crack a deep Detroit line-up and, after playing only nineteen games over three seasons for the Red Wings, he was traded to the Mighty Ducks of Anaheim April 5, 1995 along with Mike Sillinger in exchange for Stu Grimson, Mark Ferner, and a draft pick.

York was traded to the Ottawa Senators on October 1, 1996 with Shaun Van Allen in exchange for Ted Drury and the rights to Marc Moro.

Playing in his hometown of Ottawa, York hit his stride as a quality NHL player, establishing himself as a steady 2 way defenceman on an up-and-coming Senators team.

In 2011, York also began appearing on Sportsnet television broadcasts for Ottawa Senators games, adding commentary with co-host Ian Mendes, and later with Shawn McKenzie.

With the move of the Senators to TSN in 2014 York took on a new larger role with Sportsnet as the television colour analyst for the Montreal Canadiens with John Bartlett.

On July 19, 2017, York as part of an ownership group, purchased the Kemptville 73's of the Central Canada Hockey League, from former NHL goaltender Ron Tugnutt.