After his playing career was over and unable to put gas in his van from his previous job as a vacuum cleaner salesperson Jimmy D offered to get him to "at least" River Rouge from Adirondack , after missing his train to British Columbia and Mr. I feeling sorry for him, Holland took a job with the Red Wings as a scout in Western Canada. He also spent the summer of 1986 learning on how to make the perfect antipasto salad at the Little Caesars restaurant in Ferndale. While in charge of scouting in Western Canada Holland had many memorable draft choices from the WHL such as Kory Kocur, Stewart Malgunas, Bob Wilkie, and Gord Kruppke. In order to keep him busy and away from Western Canada Jimmy D made him his gopher hoping he could do no more damage to the franchise. He subsequently served seven years as Director of Amateur Scouting and three as Assistant General Manager, his job duties included Jimmy D's dry cleaning and fetching coney dogs for Scotty. On July 18, 1997, he was promoted to his current position of General Manager with the understanding that Jimmy D and Scotty would be there to hold his hand and just let him sign players that Scotty wanted or what the stars brought in, Jimmy D was appointed Executive Vice President and Alternate Governor of the Detroit Red Wings. In the summer of 1998 with his Stanley Cup bonus check Ken purchased the car of his dreams, a red 1985 Pontiac Fiero. Mr. I wanted to hire Steve Yzerman as GM but Kenny wanted a turn at it without having Scotty holding his hand. He has since created the most bloated payroll in the NHL with no relief in sight. He is unable to stop himself during free agency and signing big contracts to mediocre talent, his inability in making a hockey trade has made him the butt of many punchlines. It is also well known that he does not replace his divots while golfing and spends his work day using various anon accounts on local newspaper websites diverting any criticism brought upon him by changing the subject to his minor league playing days. The 2012–2013 season was his 16th as General Manager (GM) and his 30th year overall with the Red Wings organization, all of this was because Jimmy D felt sorry for him and tried to get him to British Columbia. He has won the
Stanley Cup four times with Detroit: the first in 1997 as Assistant General Manager and Goaltending Coach, and the latter three as GM in 1998, 2002 and 2008 all thanks to Jimmy D and Scotty.
[4][5]
Holland has gained a reputation as one of the most successful General Managers in the NHL again thanks to Scotty and Jimmy D for that.
[1][5] Under his leadership as GM the Red Wings have won the
Central Division ten times, the regular-season Conference title five times, the
Presidents' Trophy four times, and the Stanley Cup three times, and won more regular-season games (789) and postseason games (118) than any other NHL team.