(Photo be Kevin Mathewson, Kenosha County Eye)
KENOSHA, Wis. — The City of Kenosha and former Kenosha Police Officer Joshua T. Sylvester have agreed to a $450,000 settlement with Alessandra Dashawn Doby, a Kenosha woman who accused Sylvester of sexually assaulting her while she was intoxicated and in police custody in August 2022. The settlement ends a federal civil-rights lawsuit filed by Doby, whose attorney, Keenan J. Saulter, previously attempted unsuccessfully to restrict Kenosha County Eye’s reporting about his client. Since making the allegations against Sylvester, Doby has also been arrested in a separate drunk-driving case involving a crash with a Kenosha County Sheriff’s Department jail transport van. Newly reviewed police body-camera transcripts from that arrest document Doby repeatedly berating officers, using racially charged language, threatening violence, and telling officers to kill themselves.
(Racine County Sheriff’s Office)
The $450,000 settlement was disclosed in documents obtained by Kenosha County Eye following the dismissal of Doby’s federal lawsuit. The agreement provides for payment to Saulter Law P.C.’s trust account, with the amount inclusive of attorney fees and litigation costs. The agreement also releases Sylvester, the City of Kenosha, Cities and Villages Mutual Insurance Company, and other covered parties from claims associated with the litigation. It does not specify how much money Doby will personally receive after attorney fees and expenses, nor does it establish which entity will ultimately fund the settlement.
Importantly, the settlement contains an express denial of liability. Neither Sylvester nor the City of Kenosha admits wrongdoing by entering into the agreement. The federal lawsuit is being dismissed with prejudice, meaning Doby cannot bring the same claims again.
(Kenosha County Sheriff’s Office)
(Kenosha County Sheriff’s Office)
Former Officer Accused Of Sexual Assault While Guarding Intoxicated Woman
The allegations against Sylvester date back to August 2022, when he was assigned to guard Doby, who had been taken into custody and transported to Aurora Medical Center in Kenosha. Authorities alleged Sylvester sexually assaulted Doby while she was intoxicated and under his supervision. The incident was investigated after allegations of misconduct surfaced, and investigators reviewed evidence that included footage from Sylvester’s department-issued body-worn camera.
Sylvester was subsequently arrested, criminally charged, and terminated from the Kenosha Police Department. Despite his firing, he later sought to regain his position with the department. Kenosha County Eye has extensively covered the allegations, Sylvester’s termination, his efforts to return to the department, and the subsequent criminal and civil proceedings.
In August 2025, Doby filed a federal lawsuit against Sylvester and the City of Kenosha, seeking damages arising from the alleged assault. The lawsuit accused Sylvester of violating her constitutional rights and sought to hold the city responsible for the alleged misconduct.
The civil proceedings nearly ended earlier this year for reasons unrelated to the merits of Doby’s allegations. In March 2026, Kenosha County Eye reported that U.S. District Judge J.P. Stadtmueller nearly dismissed the lawsuit after Saulter failed to comply with a court deadline for several months. The judge ultimately allowed the case to continue.
The case has now ended through the negotiated $450,000 settlement rather than a civil trial or jury verdict.
Attorney Previously Tried To Gag Kenosha County Eye
The settlement follows an unsuccessful effort by Saulter to restrict media coverage of his client during Sylvester’s criminal proceedings.
In October 2025, Saulter asked Kenosha County Circuit Court Judge Jason Rossell to prohibit Kenosha County Eye and other media outlets from publishing Doby’s identity, seeking to require reporters to identify her as Jane Doe. Doby had already been publicly identified in previous reporting, and Kenosha County Eye opposed the proposed restriction on First Amendment grounds.
On November 3, 2025, Rossell denied the request in open court. The ruling allowed Kenosha County Eye to continue reporting Doby’s identity and the proceedings without the requested judicial restriction.
Saulter’s relationship with Kenosha County Eye became contentious again earlier this month when the publication contacted him for comment about the apparent resolution of the federal lawsuit.
On October 6, Kenosha County Eye asked Saulter whether the case had settled, how much his client would receive, who would be responsible for payment, and whether the agreement contained confidentiality provisions. Saulter did not provide substantive answers to those questions in the correspondence reviewed by Kenosha County Eye.
Instead, Saulter responded to the media inquiry in a manner Kenosha County Eye considers unprofessional. Rather than addressing the questions concerning the use of potentially public funds and the settlement’s terms, the attorney engaged in a contentious exchange with the publication’s editor.
Doby Later Arrested After Crashing Into Jail Transport Van
Doby’s legal troubles did not end with the allegations against Sylvester.
On April 6, 2025, Doby was arrested after allegedly driving while intoxicated and crashing into a Kenosha County Sheriff’s Department jail transport van near 75th Street and 60th Avenue in Kenosha.
The van was transporting an inmate, Spartacus Outlaw, who suffered reported neck and back injuries and was taken to Froedtert Pleasant Prairie Hospital for treatment.
According to the criminal complaint and police reports previously reviewed by Kenosha County Eye, officers found eight empty White Claw alcoholic beverage cans and three miniature Tito’s vodka bottles in Doby’s vehicle. Doby allegedly admitted to drinking and described herself as an alcoholic.
The incident resulted in criminal charges that included operating while intoxicated causing injury, resisting an officer, and disorderly conduct. Doby was subsequently released on no-cash bail.
The arrest was particularly noteworthy because Doby had previously been arrested for operating while intoxicated in August 2022. In that earlier incident, police reported a blood-alcohol concentration of 0.242, more than three times Wisconsin’s standard legal driving limit of 0.08.
Despite that reported level of intoxication, the earlier municipal OWI prosecution was dismissed by the Kenosha City Attorney’s Office. That dismissal meant Doby did not receive an OWI conviction from the earlier case, leaving the subsequent arrest to be handled without a prior OWI conviction from that incident.
Body-Camera Transcript Reveals Threats, Profanity And Racially Charged Language
Kenosha County Eye has now reviewed a 15-page AI-generated transcript of police body-worn camera footage documenting Doby’s conduct during the hospital blood-draw process following her April 2025 arrest.
The transcript portrays an extraordinarily confrontational encounter in which Doby repeatedly cursed at officers and medical personnel, mocked their physical appearances, used racially charged language, and threatened violence.
At one point, Doby appeared to threaten an officer with physical violence, stating, “I should have kicked you in the motherfucking face and took the charge.”
Later, she threatened to break someone’s nose and accept the criminal consequences. She also suggested she would encounter an officer after his shift ended.
Doby repeatedly told officers to kill themselves, including one statement in which she told an officer, “Hey, when you get home tonight, you should think about killing your fucking self. Make the world a better place.”
The transcript also contains repeated uses of the N-word and derogatory comments about white people. Doby repeatedly mocked one officer’s height and another person’s red hair, referring to the latter with insults throughout the encounter.
During the blood-draw process, officers warned Doby that fighting or injuring anyone could result in additional criminal charges. The transcript includes an instruction to stop resisting, as well as Doby repeatedly demanding that officers remove their hands from her.
Medical personnel apparently encountered difficulty obtaining an adequate blood sample, and multiple attempts were discussed. Doby insisted that her blood was difficult to draw and accused those attempting the procedure of incompetence.
At another point, she threatened to spit in someone’s face but suggested she was restraining herself because of the potential consequences.
The AI-generated transcript contains apparent speaker-identification and transcription errors. Kenosha County Eye has therefore treated the statements as preliminary transcriptions of the body-camera recording. Although the transcript documents threats to kick officers, the written material alone does not conclusively establish whether a kick was physically attempted.
Could The $450,000 Settlement Become Evidence In Sylvester’s Criminal Case?
The substantial civil settlement could also become an issue in Sylvester’s criminal proceedings if his defense attorneys seek to question Doby about a possible financial interest in the allegations.
Wisconsin law generally permits attorneys to explore a witness’s potential bias, prejudice, or financial interest when challenging credibility. Wisconsin Statute § 906.16 allows evidence of witness bias, while § 904.08 provides exceptions permitting settlement evidence to be introduced for purposes other than proving liability, including demonstrating potential bias.
Sylvester’s attorneys could potentially argue that Doby’s pursuit of substantial financial compensation created an incentive to maintain or embellish her allegations. However, Doby initially made the allegations in 2022, years before the settlement was reached, and the settlement does not establish that her accusations were fabricated.
The defense could seek to introduce the existence of the civil settlement or question Doby about her financial interest. Whether the jury would be permitted to hear the actual $450,000 amount would be a separate question for the trial judge. Wisconsin courts have recognized circumstances in which the existence of a settlement may be relevant to credibility while its monetary amount is excluded.
The civil settlement also does not determine Sylvester’s criminal guilt or innocence. The criminal case involves a different burden of proof, and the settlement expressly disclaims any admission of wrongdoing.
Settlement Ends Federal Lawsuit, But Questions Remain
The settlement brings an end to more than a year of federal civil litigation and a controversy that began with Sylvester’s arrest and termination more than four years ago.
The agreement provides for payment within 30 days after the required executed release and documentation are received. It also includes standard provisions resolving claims against the defendants and other released parties.
Although the agreement identifies Cities and Villages Mutual Insurance Company among the released parties, the documents reviewed do not establish precisely how the $450,000 payment will be divided among the city, its insurer, or other sources.
The settlement also leaves unanswered how much of the $450,000 will ultimately go to Doby personally and how much will be retained for legal fees and litigation expenses.
Kenosha County Eye will continue following the criminal proceedings involving Sylvester and Doby’s separate OWI-related case, including any future court rulings concerning the admissibility of the civil settlement.
5 Responses
A bunch of dumbasses all around.
Failure wanna be cop who should’ve been labeled a sexual predator. No department should ever hire him.
Dumb drunk girl. She was a victim and had every right to burn everyone involved. But no one bothered to get her help to stop boozing? Her settlement will mostly go to her lawyer and she’ll drink the rest.
Spartacus Outlaw is a crazy name for an inmate
Someone made advances to that??? Unreal.
Good article!!
With that thing?..