Joey Smallwood was born in 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 an underground newspaper of his own in Corner Brook.