Keena Allen’s office could belong to a beloved school principal or guidance counselor, its shelves packed as they are with mementos, a ceramic cross and decades of awards and certificates.
But Allen’s crisp, green uniform and the title on her office door — director of inmate services — quickly make it apparent that Allen deals not with troubled students in detention, but with troubled adults in the detention center — the jail, the joint, the slammer, or, as the facility is affectionately known by locals, the Stock Island Hilton.
“Ms. Allen,” or “Director Allen,” as she’s known at work, is a sweet badass whose eyes smile brightly behind her COVID mask — until someone downstairs crosses a line.
“I learned long ago that I’ll never know someone’s whole backstory or the whole situation that brought them here,” Allen said. “I don’t look up their cases and I don’t judge them. That’s not my job. I treat them like the human beings they are, with the same level of respect they show me.”
Allen joined the Monroe County Sheriff’s Office as a corrections deputy in 1990 after completing a tour in the U.S. Army. (See? Badass.)
“Back then, we were still in the old jail on Whitehead Street,” Allen recalled. “That was like the old-time prisons, with the clanking doors, bars and some crowded dormitory-style units.”
Two particular inmates stand out in her memory from the early days, when she was a new deputy at the old jail.
“One guy’s nickname was ‘Razor Face,’” Allen said. “He had tried to cut someone with a razor, but instead got his own face all sliced up. He was trouble, always angry, always in lockdown. And that was scary in the beginning for me.”
Allen remembers another inmate, a “frequent flyer,” who returned regularly for being drunk in public.
“He was a big, burly, homeless man,” she said. “And he’d get drunk and arrested every once in a while so he could come in and get a shower, a shave and a couple meals, like the old ‘three hots and a cot’ scenario. He was always good to me. He followed my rules and always did what was expected of him. He reminded me of the old gentle giant cliche.
“Then, once we started entering fingerprints in the Integrated Automated Fingerprint Identification System (IAFIS), it turned out he was wanted for murder in California and had been hiding out as a homeless guy in Key West,” Allen said, shaking her head at the memory.
Overcrowded and crumbling, the old jail closed in 1994, when the current detention center opened on College Road, next door to the sheriff’s office headquarters.
Sheriff Rick Ramsay was making the rounds in the detention center on Feb. 9 and poked his head into the conference room while Keys Weekly was speaking with Allen.
“She’s fantastic,” Ramsay said. “Always up. Always smiling. Always bright. I swear, she never seems to have a bad day. We’re lucky to have this woman.”
So are the inmates whose programs and services Allen directs, everything from their mail, phone calls, visitation, laundry and library access, to AA and NA meetings, the successful fatherhood initiative, religious services and kosher meals for Jewish inmates — “actual Jewish inmates,” Allen clarifies, “not the folks who try to game the system by claiming they’ve converted to Judaism just to get a kosher meal.”
After working for years as a detention deputy inside the jail, Allen was promoted through the ranks to records supervisor, records director and finally to director of inmate services.
“I work with an amazing team of people, and we all came up through the ranks together and have worked together in the trenches, so we know what each other is dealing with,” Allen said. “I simply love my job; I always have. I only have three years left until retirement, but who knows? I may wait a year after retirement, and then come back.”
Allen has seen classmates from Key West High School get fingerprinted and booked into the jail. She’s had the children of her friends in the jail and some of her own friends as well.
“I’m not here to judge,” she said. “The courts do that. And I always remind myself that we’ve all likely done something at some point that could have landed us here. We’re all human and we all deserve respect when we give it.”
