Bossy was educated at Pain Court, Ontario, and worked for many years as a farmer, and a traveling fertilizer salesman for Canada Packers.
He served on several Kent County School Boards in the late 1960s, and was also a member of the Royal Canadian Legion and Knights of Columbus, was active in RC Parish Council in both home parishes in Dresden and Chatham, performed as part of a local dance band specializing in polka music.
The Liberals were defeated in the 1984 federal election, and Bossy lost to Progressive Conservative Elliott Hardey by over 5,000 votes.
[3] The Liberals formed a minority government after this election and Bossy was appointed as parliamentary assistant to the Minister of Housing in 1987.
[4] The Liberals were defeated in the 1990 provincial election, and Bossy too, losing his legislative seat to New Democrat Randy Hope by almost 4,000 votes.