Oscar Ray Bolin Jr and Rosalie Martinez: Hybristophilia Series

Dr. Ari Gartin, Ph.D., Clinical and Forensic Psychologist

Oscar Ray Bolin Jr. was a convicted serial killer whose crimes shocked the state of Florida and gained national attention. Born in 1962, Bolin was sentenced to death for the brutal murders of three young women in the Tampa area in 1986: Natalie Holley, Stephanie Collins, and Teri Lynn Matthews. His crimes included kidnapping, sexual assault, and homicide, with each case displaying signs of premeditated violence and sadistic control. Bolin had a history of violent behavior and was also linked to a fourth murder in Texas. Despite multiple retrials, which briefly vacated his convictions due to procedural errors, final juries reaffirmed his guilt, and he received three death sentences in Florida. Bolin's convictions were supported by strong forensic evidence, including testimony from his brother-in-law, a bloody towel with his fingerprint, and the testimony of a witness who claimed he had confessed. His appeals were repeatedly denied over the years, and he ultimately spent nearly three decades on death row.

What set Bolin apart in the public imagination, however, was not only his crimes, but the woman who fell in love with him. Rosalie Martinez was a well-known public figure in Tampa, working as a mitigation specialist for the Hillsborough County Public Defender’s Office. She was married to a prominent attorney and had four daughters. Yet in 1995, she was assigned to Oscar Bolin’s case and began investigating his conviction. Throughout reviewing evidence and meeting with Bolin, Rosalie became convinced he was innocent. Moreover, she became emotionally entangled. In 1996, she made the radical choice to divorce her husband and marry Oscar Bolin in a speakerphone ceremony while he was incarcerated on Florida’s death row.

Rosalie’s childhood remains less publicly documented, but her adult life before Bolin was marked by affluence, professionalism, and a high level of community standing. Her pivot toward Bolin represents a striking departure from her previous identity. She has spoken about feeling emotionally starved in her prior marriage, and described Bolin as someone who gave her the kind of passionate attention and emotional reverence she had never experienced. Despite the horrific nature of his crimes and the weight of the evidence, she believed he was a victim of a broken justice system. She saw herself not only as his wife, but as his advocate and voice—a woman uniquely positioned to fight on his behalf.

Their marriage, held on October 5, 1996, occurred via speakerphone from her home. Just three days later, Bolin received yet another death sentence in court. Despite the legal setbacks and eventual execution, Rosalie remained devoted to him throughout his incarceration. She described their relationship as deeply emotional and intimate, even without physical contact. She visited regularly, wrote to him often, and advocated tirelessly in media interviews, asserting his innocence to the public. The paradox between her fierce belief in his redemption and the gruesome realities of his crimes was a tension she carried until his death.

Oscar Ray Bolin was executed by lethal injection on January 7, 2016, at Florida State Prison. His execution was delayed slightly that evening to allow the U.S. Supreme Court to review a last-minute appeal, which was ultimately denied. Rosalie Martinez was reportedly in attendance, continuing to insist on his innocence until the end. After his death, Rosalie largely retreated from public view. While she continued to work in legal and mitigation-related fields, she no longer maintained the same level of visibility she once had during her marriage to Bolin. Her story remains one of the most striking modern examples of emotional entanglement between a death row inmate and a professional advocate.

Rosalie’s story has been widely debated as a textbook case of hybristophilia, also known as the paraphilic attraction to those who commit violent crimes. But it is also layered with psychological complexity. Her attraction to Bolin cannot be reduced to a fetish alone. It involved emotional identification, savior fantasies, trauma reenactment, and likely a deep-seated need to feel uniquely needed and seen. Her background as an investigator and her access to court documents only deepened her sense of purpose and righteous alignment with Bolin’s cause. For her, it wasn’t just love—it was a mission.

Clinically, this case also sheds light on a recurring phenomenon within correctional environments: the emergence of romantic or sexual relationships between offenders and those who work within or around the justice system. Research and forensic case reviews have documented numerous instances in which inmates develop emotional or sexual connections with counselors, guards, attorneys, or investigators. These relationships often stem from complex transference dynamics, trauma bonding, and the illusion of emotional intimacy within a controlled environment. The offender may idealize the staff member as a rescuer, while the staff member may feel emotionally validated or powerful in the presence of someone who appears vulnerable despite a violent past. These relationships blur ethical lines, complicate professional boundaries, and in cases like Rosalie's, alter the trajectory of lives and legal cases entirely.

Copyright © Gartin, 7/6/2025