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.

[1] Cleary also earned a reputation as a steadfast Newfoundland separatist, such as in May 2008, when he wrote "I don’t want to seem ungrateful, but now that we’re rolling in the cash it may be time to consider breaking away from the country of Canada.”[2] When The Independent went out of business he went on to host Nightline, a VOCM radio call in program.

Cleary first entered politics when he became the New Democratic Party (NDP) candidate in the riding of St. John's South—Mount Pearl in the October 2008 federal election.

His candidacy led to some controversy for him and NDP leader Jack Layton for comments Cleary had written only a couple of years before when he was a journalist.

Cleary had referred to NDP supporters as a "small pocket of aging granolas and artsy-fartsies" and that they were "a mainstream party that wouldn't win an election if Jackie Layton was given a 100-seat head start.

[16] He won the Progressive Conservative nomination but was defeated in the general election by Liberal incumbent Cathy Bennett.

[21] On December 3, 2019, Cleary announced the disillusion of FISH-NL after it failed to gain the necessary 4000 signatures after a second membership drive to trigger a ratification vote.