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Smallwood was born at Gambo, Newfoundland, on December 24, 1900. When he was only five months old his family moved to St. John's. Smallwood dropped out of school before graduating; when he was fifteen years old he apprenticed as a printer at a newspaper in St. John's before becoming a reporter. In 1920 he moved to Halifax, then to Boston and New York City, gaining more experience as a newspaper reporter. After travelling to England in 1926 he returned to Newfoundland.
In 1946 Newfoundland had a National Convention to decide whether to enter Canada or remain a colony of Britain. Smallwood, or "Joey" as he came to be called, believed that Confederation was the right choice for Newfoundland. He became involved in politics to convince his fellow Newfoundlanders to join Canada, and he was a member of the team sent to Ottawa to check out what Canada might offer Newfoundland to join. He became leader of the Liberal party in 1949, and remained premier for almost a quarter of a century. After retiring twice, only to come back twice, he finally retired for good in 1977. Besides politics, Smallwood's main interest was the history of Newfoundland. He started the Encyclopedia of Newfoundland, but died on December 18, 1991 before it was finished.