(File Photo by Kevin Mathewson, Kenosha County Eye)
[Content Warning: This article contains graphic descriptions of alleged sexual assault.]
KENOSHA, Wis. — Alessandra Doby is suing the City of Kenosha and a now-fired police officer in federal court, alleging she was sexually assaulted in a hospital room while handcuffed, intoxicated, and in police custody.
(Kenosha County Sheriff)
The civil rights lawsuit, filed on August 18, 2025—exactly three years after the alleged assault—accuses former Kenosha Police Department officer Joshua Sylvester of committing a prolonged sexual assault against Doby on August 18, 2022. The suit also claims the city failed to prevent the abuse and should be held liable for his actions.
The filing date is significant: it falls on the final day of the three-year statute of limitations for federal civil rights lawsuits under Section 1983 in Wisconsin.
“Horrific and Vile” Assault Allegedly Captured on Camera
After crashing her vehicle into a tree in Kenosha’s White Caps neighborhood, Doby—whose blood alcohol content was later measured at 0.242—was taken by ambulance to Aurora Medical Center. There, Sylvester was assigned to monitor her in custody while she sobered up.
According to police reports and court filings, Sylvester used this time to isolate and sexually exploit Doby over several hours. Surveillance and body-worn camera footage allegedly shows him exposing himself, digitally penetrating Doby, and adding himself as a contact in her phone to send nude photos of her to his personal device.
The camera reportedly captured moments when Sylvester covered the lens with his hand while moving his body close to hers. In one instance, investigators say footage shows his hand thrusting between Doby’s legs, followed by visible vaginal secretions, which he wiped on a hospital linen.
Doby, who was 24 at the time, was handcuffed, severely intoxicated, and under police guard. Her attorneys argue she was incapable of consent due to her condition and custodial status.
Defense: She Was “Erotic” and Initiated It
Sylvester has pleaded not guilty and denies the allegations. In a court affidavit filed by his defense attorney, he accuses Doby of initiating inappropriate behavior and acting in a sexually provocative manner.
The affidavit claims that Doby exposed herself, fondled her breasts, and spread her legs intentionally during the hospital encounter. It further suggests she was fantasizing under the influence of alcohol, pointing to what the defense describes as her “erotic, continuous behavior.” Sylvester’s attorney argues that this could explain the presence of her DNA on his body-worn camera and raise questions about memory distortion due to intoxication.
The affidavit also characterizes Sylvester’s contact as an effort to stop Doby from masturbating. However, law enforcement investigators—who reviewed hours of video—ultimately found probable cause for sexual assault and described Sylvester’s behavior as predatory and deliberate.
He was arrested and charged with second-degree sexual assault by a law enforcement officer and misconduct in public office. He was fired by the Kenosha Police Department on August 23, 2022. His criminal trial is scheduled to begin October 13, 2025.
Lawsuit: City Shares the Blame
Doby’s federal complaint argues that the City of Kenosha is liable for Sylvester’s actions, citing a failure to supervise, train, or screen officers adequately. The lawsuit includes claims of unlawful search and seizure, cruel and unusual punishment, and gender-based discrimination.
The city is being sued under both federal civil rights law and Wisconsin’s indemnification statute, which requires municipalities to cover judgments against employees acting within the scope of their duties.
Doby is seeking compensatory and punitive damages exceeding $75,000, along with attorney’s fees.
City Prosecutor Quietly Downgraded Her OWI Case
Weeks after the hospital incident, Kenosha city prosecutor Christine Genthner amended Doby’s OWI 1st charge—stemming from that same night—to a non-criminal traffic offense. Instead of proceeding with an operating while intoxicated citation, Genthner allowed Doby to plead no contest to “Failure to Maintain Control of Vehicle to Not Cause Accident,” which carried only a $313 fine and four demerit points.
The unusual plea agreement effectively shielded Doby from an OWI conviction and the license revocation that typically accompanies an OWI, prompting speculation that the move was designed to reduce liability as the facts of Sylvester’s misconduct emerged.
(Kenosha County Sheriff)
New Drunk Driving Case in 2025
In April 2025, Doby was again arrested—this time criminally—after rear-ending a work-release van at a red light. One passenger was injured. Police said she appeared intoxicated, tried to flee, and resisted officers during a court-ordered blood draw.
Nine empty White Claws and three empty vodka bottles were found in her SUV. Doby now faces three misdemeanor charges: OWI causing injury, resisting an officer, and disorderly conduct. The OWI causing injury charge carries up to one year in jail.
Her attorneys maintain that past criminal behavior does not excuse what they describe as a constitutional violation committed by an officer while she was in police custody.
Trial Could Bring Major Payout
If a jury finds in her favor, the City of Kenosha could face a significant civil judgment. The case, now underway in U.S. District Court for the Eastern District of Wisconsin, accuses both Sylvester and the city of violating Doby’s constitutional rights under color of law.
The case remains active.
12 Responses
Classic case of he said, she said.
There’s literally footage of it. Not only from the body cam but from the hospital. Come on idiot
No he said she said. Idiot thought his body cam was off and it wasn’t.
Have we seen the footage?
Do you need to? Are you into women being sexually assaulted?
I think we all know the answer to that.
Yea, we must back the blue no matter what they do!
back the glue. pardon me i mean blue
No one knows what you meant
More like a classic case of DEI hiring practices.
Has this a hole been charged?