Born in Gander and raised in Riverhead, Harbour Grace, and Bay Roberts, Cleary graduated from the journalism program at the Stephenville campus of the College of the North Atlantic in 1989. On May 2, 2011, Cleary was elected to the House of Commons as a member of the New Democratic Party in the 2011 election. He was defeated in the 2015 Canadian federal election, after which he switched parties to run as a Progressive Conservative in the 2015 Newfoundland and Labrador provincial election and was defeated in Windsor Lake. He was president of the Federation of Independent Seafood Harvesters (FISH-NL) from its founding to its disillusion.