Home » The Enterprise: North York’s First Newspaper

Patricia Hart, surrounded by a cheerful crowd, at her 1968 book signing, Gladys Allison Library, North York (Photo: Bill Chambers)
Patricia Hart, surrounded by a cheerful crowd, at her 1968 book signing, Gladys Allison Library, North York (Photo: Bill Chambers)

The Enterprise: North York’s First Newspaper

North York’s first newspaper was founded November 11, 1926 in Willowdale. Called The Enterprise, it was established by Robert Rankin, a printer, and Thomas Osbourne, a linotype operator. They thought the market was ripe for a community paper, as North York transitioned from a rural community to an urban one. The four-page weekly paper was first produced, in what used to be a store, just north of Yonge and Sheppard.

The paper was given the colorful nickname of The Squeak. There are two versions as to why. One is that Osbourne said the first paper was so small it looked like a squeak of a newspaper. The other was explained by Bert Long, the managing editor from 1938 to 1959, “It was affectionately called The Squeak mainly because The Enterprise wasn’t a sophisticated newspaper – it was more folksy,” he said. “You couldn’t paint the front door green without it being noted in the newspaper and if your neighbours went as far as Burlington for the weekend it was sure to be in the paper next week.”

Osbourne sold his interest to Rankin two years later, in 1928. The following year, the stock market crashed ushering in the Great Depression. The paper’s circulation held steady, supplemented by free distribution, but advertising shrivelled. Barter replaced cash. Services and goods were exchanged for printing and advertising. During the Depression, William Stowe, a printer, who did some of the paper’s printing, became Rankin’s new partner.

In 1938, Rankin sold his interest to brothers William A. and George Dempsey, owners since 1921 of the general store at the corner of Yonge and Sheppard streets. At the time, the advertising rate was $0.20 a column inch, and a year’s subscription $1.00 or $0.20 an issue. Stowe sold his interest in 1940 to the Dempseys.

The Dempseys hired Bert Long, who had sold advertising for The Enterprise. Besides being the editor, Long did proof-reading, collected accounts, wrote editorials, did reporting and page layouts. All this for a salary of just $12.50 a week. Moreover, he was expected to pay his car expenses. He worked a 60-hour week.

The Dempseys dissolved their partnership in 1948, with William Dempsey choosing The Enterprise. In 1959, when Long left the paper to work for the North York school board, William’s son Douglas became editor. In 1960, The Toronto Daily Star acquired The Enterprise. Douglas Dempsey and his brother Herb, organized a new company with The Toronto Star called Newsweb Ltd., which specialized in offset newspaper printing. In 1970, Metro Mirror Publishing Ltd. bought The Enterprise.

Sample Stories (1946)

June 20, 1946: The Bell Telephone Company’s Customers Suggestion Corner for Rural Telephone Service: One customer writes: “Devise some means so that if neighbours must listen in, they can at least repeat correctly what they heard.”

July 25, 1946: With the addition of another highway patrolman there will now be five provincial policemen patrolling the Yonge Street highway between Toronto and Barrie.

July 18, 1946: Department of Health, Township of North York
About Laughter: Never laugh at your children but be sure to laugh with them. A hearty laugh, by whipping up the blood and expanding the lungs, heightens the laugher’s general sense of well-being. Carl E. Hill, M.D., Medical Officer of Health

Reeve George Mitchell of North York Township warns residents of this municipality to stop using water for their lawns and gardens or go without water from 5 p.m. until 10 p.m.

By Susan Goldenberg, Director, North York Historical Society

Originally published in the March-May 2015 North York Historical Society Newsletter