He lived in Connecticut and Washington, D.C., before moving to Beverly, Massachusetts, in 1989.
[3] In 1990, Henry challenged incumbent Frances Alexander for the 6th Essex District seat in the Massachusetts House of Representatives.
Alexander was considered one of the most likely incumbents to be defeated, however the race became close after Henry made several misstatements about his educational and professional background, which included claiming he was an accountant when he really was a bookkeeper.
[5] In 1992, Henry was the only incumbent Republican to face a primary challenger.
He lost to Democrat Michael P. Cahill in the general election 12,750 votes (65.5%) to 6,706 (34.5%).