Getting Too Close in Close Quarters
In the last 25 years, prison breaks have been facilitated by a prison tailor, a dog trainer and a psychologist, among others. They have a common denominator: An alleged "romantic" relationship between a female worker and a male inmate (or inmates).
A 2023 Department of Justice report found that "Two-thirds of those who engaged in [prison staff-on-inmate] sexual misconduct were female."
Dr. Gilmartin, a clinical psychologist and author of Emotional Survival for Law Enforcement: A Guide for Officers and Their Families, notes in the report that whereas a police officer's interaction with a criminal is often brief and can lead them to see an offender as only their crime, "C.O.s [corrections officers] see inmates for long periods of time in fairly intimate settings that can be highly emotional."
In his work, Gilmartin discovered that most corrections officers who have been manipulated by prisoners had impeccable records—and poor social connections. Generally, he found C.O.s identify more with their job than with other aspects of who they are, and when they're on a roller coaster of adrenaline-fueled work hours and a hobbyless, depressive home life, they're mentally fragile.
Longtime and even top prison employees develop risk not only for burnout, but for manipulation—especially if they're stressed over low pay, long hours and poor working conditions, says Gary Cornelius, a retired first lieutenant of the Fairfax County, Virginia sheriff's office who trains correction officers. Sharing things like marital status or criticizing a fellow officer to an inmate might be signs of a slippery slope.
Inmate-Officer Relationships Start Small
Cornelius's book, The Art of the Con: Avoiding Officer Manipulation, specifically addresses how officers can be coerced into illegal behaviors—and it starts with inmates seeing which officers will do them small favors, he tells A&E. Before helping him escape, Vicky White had reportedly given Casey White special privileges, such as extra food.
To outsiders, prison rules restricting treats and the like can sound Draconian. But Dr. Gilmartin says officials must look at everything prison workers do and assume the worst-case scenario is true—because sometimes it is.
Joyce Mitchell, a civilian prison employee who famously helped two convicted murderers escape a New York prison in 2015, had cozied up to guards by bringing in baked goods, earning special treatment and meals for the men she helped escape. At her request, guards had put the men in adjoining cells and handed frozen hamburger meat to one prisoner without putting it through a metal detector, according to CNN.
Beyond gifts, Cornelius lists some "inappropriate staff-offender involvement red flags" as flirtatious banter, an employee spending unusual amounts of time with one inmate and employee assistance in an inmate’s financial, legal or personal affairs.
Prisoners Have Nothing but Time
A criminal planning an escape tends to be someone serving a longer sentence, says Dr. Gilmartin. "If you're doing two years, and you got 20 months under your belt, you're not gonna bust out," he says. "But if I'm going away for life—what do I have to lose?"
Cornelius concurs that prisoners like these have nothing but time. "They have 365 days a year, 24 hours a day to plan these things," he says. This means a manipulative offender can slowly build up trust before pushing for help with an escape. Vicky White and Casey White allegedly had a "special relationship" for two years prior to the prison break.
Manipulative Offenders Target the Lonely
When it comes to romantic entanglements with prisoners, inmates often have a long time to survey their prey target the lonely, according to Cornelius. "We all have a need for emotional feedback," he says.
"People are only motivated by unmet needs," says Dr. Gilmartin.
It certainly was the case for Toby Dorr (then Toby Young), a dog trainer in a lonely marriage, who smuggled convicted murderer John Manard out of a Kansas correctional facility in a dog crate in 2006.
Manard "told me how nice I looked and acted like he cared about what kind of mood I was in," Dorr told Anderson Cooper during an interview on Anderson Cooper 360. "It was kind of like pouring water on a dying plant."
In an essay for Today, she called her 12 days on the run with Manard "wonder-filled" while acknowledging that if she had not been "so broken, so desperate…it wouldn't have happened."
"Seeing [a prisoner's] humanity is healthy—with a healthy employee," says Dr. Gilmartin. "It is not healthy with an unhealthy employee. There's this transference reaction because they don't have a vibrant, emotionally supportive relationship or social network at home. This is their only relationship."
Even the experts can be surprised by who this applies to. Dr. Gilmartin says he was personally shocked to learn that a female officer he worked with had been in contact with an offender's mother 23 times before he escaped custody.
