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Judge Henry is a fourth generation Texan, born and raised in the Houston area. After leaving active-duty in 1995, he moved back to League City where he has resided since then.
 
Judge Henry graduated from the University of Houston in 1987 and was commissioned a 2nd Lieutenant in the Air Force in May 1989. After completion of Undergraduate Space Training, he was assigned to the 1st Space Operations Squadron in Colorado Springs, CO. Follow-on assignments included staff positions at Officer Training School, Squadron Officer College and at the 560th Flying Training Squadron - The Chargin’ Cheetah’s at Randolph AFB, San Antonio, TX.
 
In 1995, Judge Henry transferred to the Air Force Reserve and retired in March 2010. In 2013, he started a Veterans Court Diversion Program in Galveston County to provide additional support and assistance to troubled vets who get into a run-in with the law. The program is the first veterans court in the United States that is completely staffed by veterans. In 2014, the Texas Veterans Commission named Judge Henry as being "one of the greatest veteran advocates in the whole State of Texas".
 
In 2010, he was elected in a landslide victory as the first Republican County Judge in Galveston County's history. After years of irresponsible spending and having the second highest public debt per capita in the State of Texas, he came in and kept to his campaign promises of ushering Galveston County into a 'New Era'. Judge Henry has cut the county tax rate each year he's been in office and has reduced the public debt by close to 40%. Under his leadership, the county has reached its lowest tax rate in over 15 years - not seen since the year 2000.
 
Judge Henry is also a successful businessman. He built an aviation company in Galveston County, Talon Air Services, which is an authorized vendor of aircraft parts to the United States Government and once praised by the Presidential Helicopter Squadron for its fast response to supply a critical item. He also owns one of Galveston County's largest breweries, Galveston Bay Beer Company, in Dickinson.
 
Judge Henry is the father of five children, Austin, Taylor, Jessica, and two-year old twin girls, Brinkley and Hartley. He is a commercial pilot, motorcycle rider, and family man. When he's not being County Judge or running one of his businesses, Judge Henry enjoys spending time at home hanging out with his family.