Kammala jumla mai zuwa: Detroit Red Wings sun zabi Kennedy a zagaye na huɗu (na 80th gaba ɗaya) na
1988 National Hockey League (NHL) Tsarin shigarwa. An raba lokacinsa na farko tsakanin Red Wings a cikin NHL da ƙaramar ƙungiyarsu ta Adirondack Red Wings na American Hockey League (AHL). A matakin NHL, Kennedy ya zira kwallaye biyu kuma ya kara da taimako bakwai a wasanni 20. Kennedy ya shafe shekaru hudu masu zuwa yana tsalle tsakanin AHL da NHL a cikin kungiyar Red Wings. Winnipeg Jets sun sami Kennedy daga Red Wings bayan kakar wasa ta 1993-94. Kullewar NHL yana nufin cewa Kennedy bai yi wasa da Jets ba kafin Calgary Flames ta karbe shi a kan 'yanci. Kennedy ya shafe shekaru biyu a Calgary, sannan Flames sun yanke shawarar kada su sabunta kwantiraginsa a 1996, jim kadan bayan bayyanar da cin zarafin jima'i. Ya sanya hannu a matsayin 'yan wasa kyauta tare da Boston Bruins don kakar 1996-97 amma kuma ya yi aiki tare da Providence Bruins, Boston ta AHL affiliate. Lokacin 1996-97 shine kamfen na karshe na Kennedy a cikin NHL amma daga baya ya sake fitowa a cikin kakar 1998-99 tare da Manitoba Moose na Ƙungiyar Hockey ta Duniya da ta ɓace yanzu. Kennedy ya kuma buga wa EV Landshut na Deutsche Eishockey Liga a Jamus a lokacin kakar wasa ta 1998-1999.