- November 6, 2024
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In a divorce hearing at the Flagler County courthouse the morning of July 10, Palm Coast Mayor Milissa Holland said that her husband, former head of criminal investigations at the Sheriff's Office David O'Brien, raped her multiple times while she was incapacitated in 2013, subjecting her to "multiple hours of torment and living hell."
A court document submitted by Holland's attorney alleges "multiple bodily penetrations, choking, dragging and other horrific acts. The Husband’s rape of the Wife continued for three (3) consecutive nights while the Wife was semi-unconscious to completely unconscious. The Husband has admitted in multiple writings to the Wife of the three (3) nights of rape and living Hell. The inhumane acts by the Husband has resulted in the Wife suffering permanent physical and mental trauma."
Holland and O'Brien got married in April 2012, a month after O'Brien was promoted to undersheriff and a month before Holland announced she was going to resign as a county commissioner to run for Florida House District 24.
O'Brien and his attorney, Stephen Alexander, declined to speak with the press at the July 10 hearing. Multiple previous attempts to reach O'Brien were unsuccessful.
In court, neither O'Brien nor Alexander denied the substance of the rape allegations after Holland's attorney raised them. Instead, Alexander sought to have information on the alleged rapes excluded from the legal proceedings. He said the rape allegations are past the four-year statute of limitations for prosecution that was in place in 2013, when Holland first reported the alleged crimes. (The statute of limitation has since been extended to six to eight years, but that does not apply to cases before 2015.)
Holland's attorney, Douglas Kneller, countered that evidence of the alleged rapes should be allowed in court in the divorce hearing because they are relevant to Holland's claim for permanent alimony: In most cases, permanent alimony would not be granted for a marriage that lasts fewer seven years, he said, but the law allows for permanent alimony for short-term marriages "if there are written findings of exceptional circumstances."
"Rape, we will argue to the court, when we present evidence on the facts — not mere pleadings, not allegations — that is an exceptional circumstance, assuming we agree to the proper witnesses, to link it to damages that occur for a lifetime," Kneller said. "We will show the court that his actions have disabled Ms. Holland for life with regard to her ability to earn income."
Kneller acknowledged that O'Brien had never been prosecuted or convicted. But, he said, "I have multiple writings and emails from the husband admitting that he raped his wife."
He cited a 2013 email from O'Brien to Sheriff's Office Cmdr. Steve Cole, in which O'Brien had written: "I take full responsibility for all my actions and for raping my wife and causing her so much emotional and physical pain and abuse. My inappropriate actions caused her tremendous pain and suffering, and I take full responsibility I have no one to blame but myself."
Judge Lee Smith did not rule July 10 on Alexander's motion to strike all mention of the rape allegations from the record but said he'd take the matter under advisement.
The first official report of the alleged crime came March 13, 2013, and it came not from Holland but from O'Brien. He told Sheriff's Office Lt. Jeff Stuart, who was an acquaintance, that Holland had accused him of sexual battery — rape. O'Brien did not admit to the crime, according to Stuart's report.
Stuart contacted Holland at her home, telling her what O'Brien had said, according to a State Attorney's Office investigative report.
The details of Holland's case made it particularly difficult to report, she later told the Observer, because O'Brien had only recently resigned from a position as a commander at the Sheriff's Office: She was reporting him to his recent colleagues.
Holland told investigators she had recently resigned from her position on the County Commission to run for a seat on the Florida House, but lost that race. She was feeling down.
Around the same time, Holland had a knee injury and was prescribed a course of pain medication — Tramadol. She took the medication alongside glasses of wine, and the combination left her unconscious.
Over the course of several nights, Holland told Stuart, she would go to sleep fully clothed and then wake up undressed the next morning. She had flashbacks of O'Brien raping her.
She confronted him after the first night, and he denied anything had happened.
She didn't confront O'Brien again for a number of days.
"I asked him a few days later, and he admitted to all of it," she wrote in a statement. "He said he didn't know why he did it, and felt horrible about it."
By then, too much time had passed for the Sheriff's Office to seek physical evidence. Stuart gave Holland a domestic violence information packet, then told O'Brien that Holland had reported being a victim of sexual assault. Stuart asked O'Brien if he wanted to make a statement, and O'Brien "advised me that he did not wish to at this time," Stuart wrote in a Sheriff's Office case report.
Two days after meeting with Stuart, Holland met with a State Attorney's Office investigator, a victim's advocate and Assistant State Attorney Melissa Clark.
Holland was placed under oath and completed a sworn statement, repeating the allegations that she had reported to Stuart, with more details. After the first night that she'd gone to sleep clothed and awoken undressed and "feeling strange." On subsequent nights, she was "aware of the activity and remembered being ... exploited sexually" by O'Brien, according to the State Attorney's Office report.
The dates were within Feb. 7-11: She knew, because she'd first taken the prescription Tramadol on the date it had been prescribed — Feb. 7 — and then for four more days.
On March 5, after she had confronted him, O'Brien was given a poor performance review by then-undersheriff (now sheriff) Rick Staly, and was forced to resign or be fired. O'Brien resigned.
Holland told the State Attorney's Office staff during the meeting that O'Brien had admitted to her "that he did not know why he had done what he did, that he knew on the first night that it was wrong but continued to do so."
O'Brien remained at the house for several more weeks, though he slept in a separate room. On March 12, Holland, feeling powerless, told him to turn himself in "or do something about it," according to the report. He went to Stuart the next day. O'Brien later moved out of the house, but continued paying Holland's regular bills.
Holland and O'Brien discussed the alleged rape in text messages, which Holland turned over to the State Attorney's Office.
Holland also placed a "controlled call" — a phone call recorded by law enforcement — to O'Brien on March 16.
In the call, she told him that she needed help to piece together what had happened to her. She mentioned the alleged rapes. He didn't deny them. But he told her repeatedly that he wouldn't talk with her about the issue over the phone.
In one part of the conversation, Holland tells O'Brien that she remembers him raping her. The conversation continues as follows:
(Holland): I remember it, but just bits and pieces. I know it went on for hours. What did you do after that?
(O'Brien): Mumbles. I said I didn't do anything. I didn't do anything after.
(Holland): What do you mean? You just went to sleep
(O'Brien): We shouldn't be talking on the phone. We should be in counseling for this.
And later in the same conversation:
(Holland): I feel like I walk around in a continual nightmare and it never goes away. I'm trying to get my life together after you blew it apart
(O'Brien): I know.
(Holland): And you take no responsibility
(O'Brien): I take responsibility
(Holland): I think you don't get it. I think you walk around like it was nothing.
(O'Brien): No I don't
Later, Holland asks O'Brien, "How do you live with yourself knowing you raped (redacted)," and O'Brien replies, "I don't live with myself at all."
But Holland told the investigator that she did not want to pursue prosecution, saying, "She feels it is in the best interests of herself and her family not to pursue this matter further," according to the report.
Holland's daughter has a serious chronic illness that required treatment at the Mayo Clinic, paid for by O'Brien's insurance. If O'Brien went to jail, Holland's daughter could lose access to health care. O'Brien also continued paying living expenses for Holland, who was not employed.
Holland later told the Observer she had to make a difficult decision at the time. Moving forward with prosecution would have meant not only risking her daughter's health care access and her own income, but likely undergoing the invasive process of testifying in court, revealing explicit details of the alleged attacks before a jury and being challenged by a defense attorney.
"Victims oftentimes have to go through a very difficult process all over again, in a very public manner," she said.
She told the Observer she wasn't ready for that at the time. Holland signed a form called a "declination of prosecution" on March 19, 2013, and the case was closed.
A few weeks after the statute of limitations ran out this year, O'Brien closed a joint bank account with Holland and filed for divorce. In the court documents, Holland's attorney suggests that timing was intentional.
Holland was left with almost no money: Her attorney stated in court that he'd been paid a $1 retainer. O'Brien's insurance also would no longer protect Holland's daughter.
"Therefore, in addition to the horrific raping of the Wife for three (3) consecutive nights, he has now left her without funds to maintain her ongoing bills to have even a modicum of dignity during the temporary aspect of this case," Holland's court documents state.
Holland is seeking temporary alimony of $5,000 per month, plus permanent alimony of an amount that has not yet been determined.
The next hearing is in August. In the meantime, she said she hopes to get involved in the Sheriff's Office's new task force on combatting domestic violence.
"This whole thing is very sad to me: You know, it’s sort of strange, because I go back and force with feeling conflicted over the whole thing," Holland said. "But I need to hold my head high, and this does not define me as a person, but rather ... one of many chapters in my life as it progresses."
