A 26-year-old Coupeville man is being held in jail without bail after he was accused of viciously beating his girlfriend, who recently gave birth to his child, less than a year after he was charged with raping and assaulting a different woman, according to court documents.

Bailey Rosenthal appeared in Island County Superior Court Tuesday. Judge Carolyn Cliff found probable cause existed to believe he may have committed the crime of assault in the second degree, a domestic violence crime.

Much of the discussion in court concerned Rosenthal’s alleged history of violence against women, both past convictions and the case that hasn’t gone to trial. Deputy Prosecutor Michael Safstrom noted that Rosenthal has a juvenile criminal history, which he felt was relevant when considering release conditions. Records show that Rosenthal was charged in juvenile court with domestic violence in five cases, including one in which he was accused of stomping on his former girlfriend’s stomach while she was pregnant.

This week, Safstrom asked the judge to set bail at $100,000 on the new charge and to revoke bail on the case from 2025.

In the older case, prosecutors charged Rosenthal on Feb. 25, 2025 with rape in the third degree, assault in the second degree with sexual motivation, two counts of assault in the third degree and unlawful imprisonment. Safstrom summarized the allegations in the case as “a prolonged, vicious campaign of physical violence, intimidation, sexual assault and dehumanization of the victim.”

During Rosenthal’s preliminary appeared in Feb. 21 of last year, the prosecutor asked Judge Christon Skinner to set Rosenthal’s bail at $70,000, largely based on the danger he presents to the community. The defense attorney suggested $25,000 bail.

Skinner, however, set Rosenthal’s bail at $2,500 cash or a $20,000 bond; Rosenthal promptly posted the cash bail and was released.

During the hearing this week, Rosenthal’s attorney, Meghan Lacey of Seattle, acknowledged that the bail in the 2025 case was very low and agreed that it would be appropriate to increase, but she argued against revoking it altogether — which she described as an extreme solution. She pointed out that Rosenthal hadn’t missed any court hearings or tried to contact victims. She also emphasized that Rosenthal wasn’t accused of assaulting strangers.

“If he were ordered to live with a specific person and, frankly, perhaps not live with a female or a partner of any kind, as both of these situations were women he lived with, I think that that should ameliorate the court’s concerns,” she said.

Lacey also said Rosenthal has a job in construction and has three children who need his financial support.

Cliff agreed with the prosecutor, finding that Rosenthal willfully violated the terms of his release in the 2025 case by allegedly committing another crime. She set Rosenthal’s bail at $100,000 in the new case and revoked bail in the older.

In the new case, a caller reported to police on Jan. 5 that she was worried her friend was abused by her boyfriend, Rosenthal. She reported that her friend sent her photos of her face, which appeared to be extremely bruised, with a request that the caller save the photos and not contact her because she needed a few days to leave the residence.

Deputy Austin Parrick with the Island County Sheriff’s Office went to Rosenthal’s home in Coupeville and spoke to the woman, who came to the door holding a 2-month-old baby. The deputy noted the extent of the young woman’s injuries, “her face badly blackened, yellow and bruised, both eyes black and nearly swollen shut. Obvious knuckle marks to her forehead and bruising throughout.”

The woman did not cooperate with police and said that she got into a physical altercation with Rosenthal when he tried to stop her from self-harm; she said they struck each other, but the deputy noted that the only visible marks on Rosenthal was an injury to a knuckle, the report states.

“The amount of force necessary to restrain an individual from harming themselves would not result in injuries to a person’s face to the extent of what was observed on (the victim),” Parrick wrote.

The case filed in 2025 involved events that allegedly occurred in 2022.

On one night, Rosenthal allegedly entered the woman’s bedroom with clenched fists, closed the door and said, “You don’t know what you’ve done. You’re in for a horrible time,” a report by Deputy Michael Sadler states. Rosenthal allegedly assaulted her, forced her to take her clothes off, made offensive remarks about her body, spit on her, prevented her from leaving and took her cell phone, the deputy wrote.

In addition, Rosenthal allegedly told her to crawl out a window and then threw water and cat litter at her, telling her she was lower than him, the report states.

On another occasion, Rosenthal allegedly raped her twice at their home, the deputy wrote. He put a pillow over her face so he couldn’t hear her sobbing and begging him to stop, the report states, which made it difficult for her to breathe.

In addition, Rosenthal was accused of strangling the woman, punching her, punching a hole in the wall, cutting up her mattress and ripping a rearview mirror off her car, the report states.