Sylvester was born in Glen Norman in Glengarry County. He spent his early years there and one of his first endeavours was to operate a service station in Alexandria on the Armouries’ Hill close to the present high school.

That was the beginning of his career as a garage operator and car salesman. In 1960, he moved to Cornwall where he opened a garage and became the American Motors dealer.

In 1966 he began his musical career when under the tutorship of Rev. John McPhail, he began singing with the Cuthbert McDonald girls and played locally for dances, weddings, concerts, etc. When their band broke up, Sylvester formed his own group. Sylvester changed the format and added singing to the already popular music and encouraged the people to dance when he sang. This was the start of show band style music in Glengarry. The band was so popular at the concerts that it was soon in demand in Glengarry, Ottawa and Toronto.

Sylvester and The Clansmen performed at fundraisers, wedding receptions, nursing homes, Glengarry Highland Games, St. Raphael’s Galarama, local concerts, the Glengarry nights at the NAC. They also released two records.

The Clansmen: Pipe Major John T. MacKenzie, Clara MacLeod, Thwyla MacDonald, Darryl McLeod, John Job, Sylvester MacDonald, Jack Smith and Lyle MacMillan.

Sylvester was always generous with his talent and played locally until 1989 when because of ill health he gave up taking bookings. He has played only occasionally since then. He hasn’t given up singing entirely; he has organized St. Andrew’s and St. Patrick’s concerts at his home parish and sings every Saturday at evening mass.