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Born in Exeter, New Hampshire, Masefield found a passion for acting at age 12 and is known for the short films "Mountebank" (2017), and "Gourd and Evil" (2016) which took home the Audience Choice Award at the Cat Fly Halloween Film Fest 2017 (Asheville, NC). He portrayed young Michael Skakel in the Oxygen channel special "Murder and Justice: The Case of Martha Moxley". Masefield was also featured in a National Ka-Dunks candy commercial (2018) and was one of the kids in Steve Martin & The Steep Canyon Rangers': "Strangest Christmas Yet" music video. He lives with his family (all actors) in Western North Carolina.