Joey Smallwood was born at Mint Brook, near Gambo, Newfoundland, to Charles and Minnie May Smallwood. His grandfather, David Smallwood, was a well-known maker of boots in St. John's. Growing up in St. John's, as a teenager Joey Smallwood worked as an apprentice at a newspaper and moved to New York City in 1920. In New York he worked for the socialist newspaper The Call. Joey Smallwood returned to Newfoundland in 1925, where he soon met and married Clara Oates. In 1925 he founded a newspaper of his own in Corner Brook.
In 1928, he acted as campaign manager for the Prime Minister of the Dominion of Newfoundland, Sir Richard Squires. He also ran as a Liberal candidate in Bonavista in 1932 but lost. During the Great Depression, he worked for various
