What Would Make a Woman Want to Marry a Serial Killer?

The small town of Starke in Bradford County, Florida, is best known for the three prisons that surround it. One of those, Florida State, houses 400 death row inmates. It is where the serial killer Ted Bundy died in the electric chair, and Aileen Wuornos by lethal injection.

In the visiting area outside, one hot and humid morning, a few women stand waiting to spend time in a visiting room with their loved ones. “Death row” is an ugly corridor with cells facing each other down a concrete walkway. There is no air-conditioning in this section of the prison and the temperature can reach 40° in summer. The inmates are alone in their cells for up to 23 hours every day, eating a diet of tinned vegetables and soya. Cases of scurvy have been reported.

Rosalie Bolin, a legal advocate on behalf of death row inmates, is here to visit a rapist and serial killer of women. But this man is not her client. Oscar Bolin is her husband.

They married in 1996 and said their vows over the phone. She wore a wedding dress and sat in her apartment and he wore his prison-issue orange boiler suit in his death row cell.

What drives women to become romantically involved with men who commit heinous crimes? I had travelled to Florida to Rosalie Bolin’s picturesque lakeside home, six miles south of the prison, to find out.

Bright, articulate and immediately likable, Rosalie is a passionate campaigner against state execution. It was in this role that she first met Bolin. He had been a drifter, a carnival worker and a long-distance trucker, had dealt in drugs and had pleaded guilty to a vicious gunpoint rape in 1988.

While Bolin was in prison for that crime, he was arrested for the murder of a 26-year-old bank cashier, Teri Lynn Matthews, who had been beaten, raped, strangled and dumped by the roadside in 1986. Soon, investigators discovered compelling evidence linking him to at least two other, similar murders the same year, of 25-year-old Natalie Holley and 17-year-old Stephanie Collins, who had been stabbed and beaten over the head. Police suspect he may be responsible for many more killings. Yet Rosalie tells me: "Oscar no more committed those crimes than I did." She accepts that he is a rapist, but avoids speaking of it.

In 1994, Rosalie was employed as a mitigation specialist for the Hillsborough County Public Defender’s Office, a job that involved examining death row cases for any evidence that would convince a jury to spare a prisoner’s life. In this role, she met Oscar Ray Bolin at the county jail, where he was awaiting retrial for one of the murders of young women.

Rosalie, who was married with four young daughters, felt that her role in life was to do everything she could to save prisoners from state execution. “The first time I was exposed to the death penalty was in tenth grade, when I was asked to write a paper on capital punishment,” she says. “I was appalled. They tell us 'don’t kill' but the state does just that. I walked into Oscar’s cell and he asked me, 'Who are you?' and I told him, 'I was sent here to help. I am your guardian angel.' He had real attitude and I was intrigued.”

The prison guard told her that Bolin was a convicted serial killer, but she decided he was innocent. “I have looked in the eyes of thousands of killers and there is a look, a toxicity, something behind those eyes. It is a sort of darkness. Oscar did not have that demeanor.”

Two weddings

Having been appointed officially as Bolin’s mitigation specialist, Rosalie left the jail with her head full of the man she was determined to help. “I didn’t quite admit it to myself at the time, but it was an immediate attraction. I can’t describe it. I sat on his bed and stayed there for eight hours. I left breathless.

“I was very fascinated by him. I ordered his file and they delivered dozens of boxes. I started going every day to see him.”

For some time, Rosalie had not been happy in her marriage to the lawyer Victor Martinez. The couple lived the life of socialites in their Tampa Bay home, often entertaining politicians and celebrities. “I wore Jimmy Choo [shoes] and always looked like I stepped out of a magazine,” Rosalie says.

Her first wedding could not have been more different from her second. When she married Martinez in 1979 in Tampa, more than 1,000 guests drank champagne and ate seafood at a luxurious hotel. She was 19, her groom 21.

After their marriage, Martinez trained as a criminal defence lawyer and Rosalie as a court reporter. After becoming pregnant she decided she could not stand doing that work any longer, “because the poor get no justice and the rich get all the justice.” She became an advocate for death row prisoners in the early 1990s.

But her outwardly perfect marriage quickly crumbled as she spent more and more time with Bolin, ostensibly helping him with his case. “People picked up on what was going on with Oscar and I because his face would change when I walked in the room,” she tells me.

During one court hearing, Bolin looked over at her and mouthed, “I love you.” A court reporter noticed. Then came the rumours that she had been caught having sex with Bolin in his cell, which she has denied. “The Christmas before I married Oscar I was hosting a party for the governor of Florida and 500 others, and someone asked me why I was sitting alone,” she tells me. “I said, ‘Because I am invisible.’ They were eating my food and drinking wine, and causing a mess that I would have to clean up the next day.

“I was a great mother and wife. I did everything I was supposed to do. But if I had stayed in that life I would be dead by now. I would have killed myself.”

What caused the breakdown of her marriage? “Victor had stopped telling me he loved me years before. One morning he said to me, ‘If you go to Oscar’s trial this morning, I will divorce you.’ I was like, ‘Do what you want to do.’”

When Rosalie arrived at court, one of the reporters present handed her a yellow sticky note. It read: “Victor Martinez has filed for divorce.” “I have to tell you that I snapped,” she says. “I went to the defence table and I threw the note at Oscar and said, ‘Are you going to marry me now, you fucker?’ He said: ‘Where’s the preacher?’” They married 30 days later.

Rosalie keeps several photos of the two of them in her home. In them, she looks vibrant. Bolin, who is now 50, wears his prison-issue jumpsuit, its bright orange glow contrasting with his pallid complexion.

By the French windows in the living room I notice a wooden box. It is inscribed with the name, birth and death dates of a man Rosalie affectionately refers to as “Mr Winkles”, who was executed on death row. He had raped, tortured and murdered several prostituted women he picked up on the streets. The prison asked her to take Winkles’s ashes home after he was executed, because nobody had claimed them. She tells me that he protects her home, as “no one would dare try to get past him”. She thinks it is a cute story. I find it repulsive.

There are also many photographs of her four grown-up daughters and her grandchildren dotted around her home. Rosalie’s marriage to Bolin came at a heavy cost: she gave up custody of her children. “The press crucified me for that, but I did it to protect them.”

I ask her what the children think of her marrying a serial killer. “Oscar has been the safest stepfather they could have had,” she replies. “I have never had other men in my house, or exposed them to sexual perversions. He would never harm those girls.”

She shows me a short film that her daughter Katherine made for her graduation in response to that same question—how Rosalie’s marriage to a serial killer had affected her children. Katherine was granted permission to interview Bolin in prison, and it is clear that, despite her obvious love for her mother, she has been adversely affected by Rosalie’s choices. In the film, Katherine asks Rosalie whether she realizes how hard it was for her and her sisters, coping with both a broken home and their mother’s notoriety. They both cry.

Sexless unions

There are an estimated 100 women in the U.K. involved with men on death row in various states in the U.S., according to research conducted for Death Row Dates, a TV documentary screened in the UK in 2010 on the Crime and Investigation Network. The U.S. Federal Bureau of Prisons does not keep statistics on how many marriages take place in its jails, but in 1987 the U.S. Supreme Court ruled that prisoners had a constitutional right to marry. The comedian Catherine Tate satirised women who marry men on death row with a sketch in which a British woman travels to Texas to marry a cannibalistic serial killer. “He only ate a bit of one of them,” she says, as she justifies her love for him, “when he was a student.”

Women involved with men on death row trot out explanations for why their marriages are not so different from the rest—that most marriages are loveless and sexless, anyway; that many couples do not spend much quality time together. They often tell you, as a “joke”, that at least men on death row do not cheat on their wives.

“People say we are unable to have a proper relationship because we can’t have sex,” Rosalie says. “But what if your husband is disabled, or in the military? Oscar has never been mean to me or talked to me ugly, or flirted or written another woman.”

She says that she identifies with Bolin, comparing her life as an unhappy socialite with his own as a neglected and abused child, violent criminal and now death row inmate. “I felt his isolation, his confinement, his loneliness. It affected me because I felt the same way,” she says.

Rosalie Bolin is far from the only woman to feel fascinated by, and attracted to, an inmate. There are at least 40 websites devoted to finding pen pals for prisoners in the U.S., such as writeaprisoner.com, friendsbeyondthewall.com, and convictmailbag.com. Some charge for their services and most allow you to specify in detail what kind of pen pal you desire—for example, the age of the prisoner and the crime committed. Many also have a specific “death row” category.

During my time in Starke, I began to see these women similarly to the white female sex tourists in Jamaica on whom I once did some research. The class privilege is all too apparent, as is the eroticization of “otherness” and the image of the caged beast looking for its savior. It is easy to tell the “death row divas” from the veterans. The women who have been with the men from before their convictions often appear to be poor and suffering from mental and physical ill-health. The tourists are sweet-smelling, well dressed and, invariably, white. They talk of having “rescued” men whom no one else wants.

Take Corrine. She is from Zurich and met her husband, a much younger African-American death row inmate, through a pen pal scheme eleven years ago. They married a year later.

Three times a year, Corrine flies from Switzerland to Jacksonville, Florida, and then travels the hour and a half to Starke where she has recently bought a tiny house, just minutes from the prison. Her husband, who, another visitor tells me, committed a cold-blooded murder and has served 17 years on death row, had a troubled upbringing. “I have learned not to speak to others about my circumstances,” says Corrine, a delicate-looking and attractive woman who recently retired from her university administrator’s post, “because people just don’t understand.”

At Florida State Prison, Rosalie walks the gauntlet through the concrete paths and barbed wire to see Bolin. A television antenna marks the spot above the death chamber, in the middle of the grey building. Just opposite is the area on the roadside marked for protesters and the media. As I discover, to see a man on death row you need to get there early. There are 26 visiting slots for 400 inmates.

In spite of the media portrayal of women who marry men on death row as unhinged, these women seem well adjusted, with good social skills. “Women who get into relationships with death row prisoners often have much in common with those who spend their lives creating shrines to and writing to celebrities,” says Dr Lorraine Sheridan, a forensic psychologist with the Sellenger Centre for Research in Law, Justice and Social Change at Edith Cowan University in Joondalup, Western Australia.

“These women have a relationship, in their perception, with an exciting, high-status person,” she tells me. “The death row romances take this a step further, in that they are able to have a reciprocal ‘celebrity’ relationship. There’s also the factor of having nabbed an ultra alpha male, one who has carried out the greatest of violent acts.”

On the way back to the guest house where I am staying, Rosalie and I pass a car with a number plate emblazoned with the slogan “Choose Life” and a picture of a couple of cute children playing together. I ask various people in the town if they think that the death penalty contradicts their religious beliefs. No, they tell me. The Bible says, “Thou shall not commit murder:” execution is a proper punishment for such heinous crimes.

Safe and protected

I also meet Sandra, a high school teacher from southern Florida who is in town to visit her boyfriend. Jim has been in jail since 1998 on a life sentence for murder and on death row since 2006, when during an escape attempt he killed two people, including a prison guard. In school term time, Sandra sees Jim every other weekend, and has recently bought a house near the state penitentiary.

They met before he committed his crimes when she was his boxing promoter, married to another man. There is more than 30 years’ age difference between the couple.

“He is extraordinarily bright, gifted and a brilliant writer. He has been incarcerated most of his life from children’s homes to youth detention,” Sandra says. “Most of them have. If I could swap my life for his I would.”

The phenomenon of women falling for dangerous criminals, or “hybristophilia,” as clinicians call it, is not uncommon. Since his arrest, the child rapist Josef Fritzl, who locked his daughter Elisabeth in a basement in Austria for 24 years and fathered seven children by her, has received hundreds of letters from women around the world.

Although a feeling of safety is inevitable when the men are on death row and will never be released alive, there have been tragic cases. Jacquelynne Willcox-Bailey’s 1999 book Dream Lovers: Women Who Marry Men Behind Bars includes the story of two middle-aged Christian sisters, Avril and Rose, who left long-term “boring” marriages for men in prison. One man had been convicted of several minor thefts; the other man had killed his previous wife. The thief killed Avril with hammer blows to the head a week after his release and the other husband ended up back in prison after attempting to cut off Rose’s ear and pull out her teeth with pliers.

Even for those not at risk of physical harm, the effects can be tough. After Rosalie married Bolin, life became very stressful for her and she soon went into a deep depression. “The press would follow me everywhere. I had the girls half the time. I gave [Martinez] custody so they were not disrupted and so they had the privilege that they were used to. I had no money.

“The day I married Oscar, the only people there for me were my parents, and yet I could fill courtrooms with the people that I have helped. I turned around and I was completely alone. I think they were afraid, because I went so against the establishment that if they had stuck around they would have been considered crazy as well.

“I could have walked away from Oscar a thousand times. I am loyal to Oscar because if I am not loyal to him I can’t be loyal to anyone. Oscar grew up in hell. If he did not have me he would have no one.”

According to Dr. Sheridan, women such as Rosalie feel that they have the love and protection of the individual, but in an utterly safe manner, and it can feed a woman’s sense of worth, particularly if, like Rosalie, she had suffered from low self-esteem in the past. “The woman can adopt a high-status role, particularly if she takes up a ‘my husband is innocent’ campaign,” says Sheridan, “thereby gaining power and fame for herself quite easily.”

I read a number of the cards and letters from Oscar Bolin. The prose is typical of love letters from prison—over-the-top schmaltz and declarations of undying love, self-illustrated and festooned with love hearts and roses. “When I see Oscar he always says I look beautiful. I am the love of his life,” Rosalie says.

Of human bondage

What I found in Starke was complicated. The women I met who are involved with death row inmates have obviously suffered from low confidence. Yet there is something grotesque about the way they objectify these men in cages and are able to exercise absolute control over them. They can have unlimited romance from letters, phone calls and visits. The inmates are grateful to the women and know that if they step out of line the contact may end. The women can be both rescuers and rebels and they know where the men are every minute of every day until they die.

Life is significantly better for Bolin since he married Rosalie. Every month she sends him $300 to buy better food, toiletries and other “luxuries”. She has paid for his various education courses. On every social visit, she takes $50 to buy them both food and drinks.

Towards the end of my stay in Starke, Rosalie began to open up more about the negative effects on her life of her decision to marry Bolin.

“I thought that if I made a big deal and I was his wife that they were going to listen [to the facts of his case] but it was in reverse. They were more interested in our love connection than me believing in his innocence. I married him because I wanted to make them listen. I had such a good professional and personal reputation but the minute I married Oscar, snap!”

I ask Rosalie about the future and if she ever fantasizes about a life on the outside with Bolin. “If Oscar was released tomorrow we would have a wonderful life. We would leave America. Oscar would be an inspirational speaker and a mentor for young people. Oscar has a lot of insight about how one wrong move can change your life. If we can get along in the most adverse of situations we can get along any place.”

Like the other women I met on my trip, Rosalie sees herself reflected in the face of her death row dandy. The class privilege of these women is clear—they overempathize with the inmates, narcissistically comparing their experiences of being unloved and isolated with that of men being treated like caged animals waiting to be killed by the state. They consider their unhappy marriages to be on a par with the often brutal backgrounds of these men and barely even stop to consider the pain of the killers’ victims or the victims’ families.

“Marrying Oscar was definitely a ‘fuck you’ gesture, but I fell in love with him because he was the person in the foxhole with me,” Rosalie says. “I was a prisoner in a different way and he was the one person who understood me, and he is the love of my life.”

As Oscar recently said, “If they opened these doors tomorrow and set me free, but I couldn’t have her, I would rather stay in here.” Rosalie believes him.