As a defenceman, McKenny played in the National Hockey League from 1966 to 1978, mostly for the Toronto Maple Leafs, in addition to a short tenure with the Minnesota North Stars.
After retiring from playing hockey, McKenny settled in Toronto where he began a career in broadcasting, most notably working as a local television sports reporter on Citytv from 1984 until 2010.
When the league folded in 1963, McKenny transferred to the Ontario Hockey Association's Toronto Marlboros who won the Memorial Cup in 1964.
[3] He struggled to stick with the Maple Leafs for several years, attributed to a poor attitude, possibly his alcoholism[1] and his antipathy towards the high-pressure style of coach and general manager Punch Imlach.
On May 15, 1978, McKenny was traded to the Minnesota North Stars for cash and future considerations (the rights to Owen Lloyd), playing in only ten games before retiring from the NHL.
After hockey, McKenny returned to Toronto and began attempting to break into the broadcasting industry, selling advertising and volunteering on the weekends at radio stations CHUM-AM and CHUM-FM.
He soon landed a gig as a colour commentator for Canadian-Italian Hockey League (CIHL) games at St. Mike's Arena, working Friday nights alongside play-by-play announcer Brad Diamond on local station CFMT-TV branded as "Multilingual Television".
[8] During their on-camera banter before and after the sports segments, lead anchorman Gord Martineau usually addressed McKenny by his nickname "Howie".
[1] In later interviews, McKenny talked about having to borrow US$70,000 from friends in order to immediately cover the U.S. airlift and hospital costs due to not having his Canadian medical insurance information on him.
air time) was McKenny's last with Citytv as the station refocused its sports coverage solely around the younger anchor Kathryn Humphreys.