[6] From the 1988-1989 through the end of the 1991-1992 season, Keenan coached the Chicago Blackhawks,[7] nearly to the pinnacle of hockey in 1992, losing the Stanley Cup to the Pittsburgh Penguins.

His time with the Blackhawks placed a heavy emphasis on physical play, with, for example, Mike Peluso accruing a remarkable 408 PIM in only 63 games in Keenan's last year as coach.

Prior to the 1993 season, he was also a candidate for the Detroit Red Wings head coaching job that eventually went to Scotty Bowman.

On May 22, 2009, after two consecutive first round playoff losses, Keenan was fired as head coach of the Calgary Flames; he had one year left on his contract.

He's also an analyst on MSG Hockey Night Live with Trautwig, Duguay, Maloney, Ken Daneyko, and Butch Goring.

[13] On April 30, 2014, Keenan's Metallurg team won the KHL championship with a game seven victory over HC Lev Praha.

On March 16, 2017, Keenan was announced as the new head coach of HC Kunlun Red Star, the KHL's first Chinese based team.

Owner Bill Wirtz did not want to lose Sutter, especially since Keenan had stated, in July 1992, that he wished to focus solely on his duties as general manager after the 92–93 season.

Keenan was even willing to publicly criticize Wayne Gretzky after he acquired the superstar in an early 1996 trade with the Los Angeles Kings.

Gretzky refused to consider re-signing with St. Louis during the 1996 off-season and opted instead to finish his playing career with Keenan's former team, the Rangers.

Keenan's resignation came shortly after he dealt Florida Panthers' franchise goaltender Roberto Luongo along with defenceman Lukas Krajicek and Florida's 2006 sixth-round draft pick (Sergei Shirokov) to the Vancouver Canucks for struggling forward Todd Bertuzzi, goaltender Alex Auld, and defenceman Bryan Allen.

It was speculated that Keenan had lost a power struggle with head coach and longtime friend, Jacques Martin, over personnel decisions.

That system was discontinued when he became the New York Rangers head coach and used Mike Richter as the regular starting goalie.