Gregory got his start in journalism delivering his hometown newspaper, the Norwich Bulletin, as a teenager, reading the front page articles on dark winter mornings as he passed under streetlights. Greg worked as a photojournalist at a weekly newspaper group in Connecticut for three years before attending the University of Montana to study journalism and Spanish. He interned at the Portland Press Herald in the summer of 1995 and the Boston Globe the following year. He was hired at the Press Herald in 1997 and over the past 20 years, he has photographed throughout Maine, covered the aftermath of the 9/11 attacks in New York City, twice embedded with Maine Army National Guard troops in Iraq, covered the aftermath of Hurricane Katrina in Louisiana and the 2010 earthquake in Haiti. In 2004, Rec was named Journalist of the Year with columnist Bill Nemitz by the Maine Press Association for their work in Iraq. After only ten years at the Press Herald, he won the Master Photographer award from the New England Society of Newspaper Editors, an award usually reserved for veteran photographers.