08/01/2026
Santa Rosa County's âMilton Hiltonâ
In the late 1970s, conditions at the old Santa Rosa County Jail in Milton, Florida, had deteriorated to the point that U.S. District Court Judge Winston Arnow ruled in 1978 that the facility violated constitutional standards due to squalid conditions. The ruling stemmed from a federal lawsuit filed against the county (and related actions involving the state Department of Corrections), which had rewritten jail standards. The decision forced the county into a multi-year, multimillion-dollar effort to replace the jail.
On a Friday in the summer of 1983 (with the first prisoners expected by mid-August), contractors turned over the keys to the new multimillion-dollar facilityânicknamed the âMilton Hilton.â Santa Rosa County Sheriffâs Capt. Ron Boswell remarked that prisoners would âhave little to complain about.â The $3.6 million complex was designed to meet roughly 50 court-mandated improvements in inmate living conditions. Features included air conditioning, separation of different classes of inmates, three hot meals a day, smoke detectors, and other upgrades.
The new jail was a buff-colored building elevated on concrete pilings over what had been a portion of Oak Street behind the County Courthouse. Patrol cars could drive underneath to unload prisoners at a downstairs booking station. It initially held about 60 cells; some inmates would temporarily double up until the old jail was renovated the following year to add roughly 40 more cells. The state Corrections Department delayed full clearance until the county hired and trained enough officers (eight new ones were scheduled around the handover). Sheriff Jim Powellâs department planned public tours and an open house so taxpayers could see how their money had been spent.
Despite the modern design and optimistic rollout, significant flaws became apparent almost immediately. The pod-style layout (pods AâF with a central observation tower) and the exterior window design proved vulnerable. Multiple escapes followed, undermining confidence in the facility. One of the most notable involved Anthony Braden Bryan (Anthony B. Bryan), a bank robber and murderer.
On May 27, 1983, Bryan robbed a bank in Grand Bay, Alabama, with a sawed-off shotgun and went on the run. In August 1983, while with Sharon Cooper, he kidnapped and murdered 60-year-old night watchman George Wilson in a crime that began in Pascagoula, Mississippi, and ended with Wilsonâs body in Santa Rosa County woods. Bryan was arrested later that month. While held in the new Santa Rosa jail awaiting trial, he escaped in July 1984 by slowly chiseling mortar from around his cell window (concealing the work with toothpaste, toilet paper, and food coloring between checks), then using bedsheets to climb out. He remained free until recaptured in Colorado in October 1985. Bryan was later convicted of first-degree murder and related charges and sentenced to death; he was executed by lethal injection in Florida on February 24, 2000.
Local accounts note that the escapes, enabled in part by design shortcomings, contributed to political consequences for Sheriff Jim Powell. The old jail, once renovated, was reused for female inmates, trustees, and solitary confinement. The âMilton Hiltonâ name stuck as an ironic label for the expensive new facility that had been meant to end years of legal and physical problems.
