[3] Henry was born in Milford, Connecticut and grew up on his parents' farm in the White Hills section of Shelton, CT.

Henry had his first major success in 1993 as a member of Team Honda, where he claimed the 125 East Supercross and the 125 National Championship.

[2] In 1994, he repeated as champion in the nationals, beating riders such as Steve Lamson and Ryan Hughes while battling a severe stomach ailment.

He moved to the premier 250cc division for 1995, where he was immediately competitive, winning Supercross mains and outdoor overalls, before a devastating injury at Budds Creek, Maryland ended his season.

While he raced and led the early part of the 1997 Supercross season on a YZ250, Henry complications from a hand injury forced him to withdraw during the middle of the series.

Tragedy would strike Henry yet again that summer, as he suffered two broken wrists at Budds Creek, mere feet away from the jump where he had his earlier injury.

He would go on to defeat Jeff Emig, Jeremy McGrath, Ezra Lusk, Kevin Windham, Mickael Pichon, and Greg Albertyn, earning five overall wins in one of the most competitive seasons ever to take the 1998 250cc National Championship at Broome Tioga Sports Center.

Henry also won a 2005 Grand National Cross Country enduro race in his first attempt on a stock Honda 450.