(Lawyer’s Website)
KENOSHA, Wis. — A federal civil-rights lawsuit filed by Alessandra Doby against the City of Kenosha and fired police officer Joshua Sylvester was nearly dismissed just over a week ago after her attorney failed to meet a court-ordered deadline for months.
(Kenosha County Sheriff’s Office)
Doby alleges Sylvester sexually assaulted her while she was intoxicated in a hospital bed at Aurora Medical Center in August 2022 after she crashed her vehicle and was taken into custody. She filed a federal lawsuit on Aug. 18, 2025 — exactly three years after the alleged assault and the final day allowed under the statute of limitations for federal civil-rights claims.
(File Photo by Kevin Mathewson, Kenosha County Eye)
But the case quickly stalled after it was filed.
On Oct. 29, 2025, U.S. District Judge J.P. Stadtmueller ordered Doby’s attorney to file an amended complaint by Nov. 12, 2025. That deadline passed without a filing.
More than three months later, on Feb. 20, 2026, the judge issued an order noting the missed deadline and directing the plaintiff to explain why the lawsuit should not be dismissed for failure to prosecute.
Doby’s attorney, Chicago-based lawyer Keenan J. Saulter, responded by asking the court not to dismiss the case and cited personal circumstances for the delay.
Just over a week ago, Stadtmueller allowed the lawsuit to continue but issued a stern warning. In a March 2 order, the judge gave the plaintiff one final chance to file the amended complaint by March 6 and stated that no further extensions would be granted. The judge also ordered Saulter to obtain local counsel admitted to practice in the U.S. District Court for the Eastern District of Wisconsin.
Court records indicate Saulter does not appear to be admitted to practice in that federal district, which is why the judge ordered him to associate with a local attorney.
Earlier Attempt To Gag Kenosha County Eye
The procedural problems come months after Saulter unsuccessfully attempted to silence media coverage of the case.
In October 2025, Saulter asked Kenosha County Circuit Court Judge Jason Rossell to issue a gag order barring Kenosha County Eye and other media outlets from publishing Doby’s name during Sylvester’s criminal trial.
Doby sought to be referred to as “Jane Doe” despite being the plaintiff in a federal lawsuit seeking damages from the City of Kenosha and despite facing her own criminal charges in a separate drunk-driving case.
The judge ultimately denied the request, allowing Kenosha County Eye to continue reporting on the case.
Prior to the motion, Kenosha County Eye contacted Saulter in good faith to explore whether a reasonable balance could be reached between transparency and privacy during the trial. Saulter declined to engage in any discussion.
His refusal to negotiate, combined with the unsuccessful attempt to silence coverage, led observers to conclude the gag-order request was largely performative and amounted to little more than legal grandstanding.
Sylvester Criminal Trial Still Pending
Sylvester, a former Kenosha police officer, was fired shortly after the alleged hospital incident and later charged with second-degree sexual assault by a law enforcement officer and misconduct in public office.
His criminal trial is now scheduled to begin June 1, 2026.
Doby Facing Her Own Drunk-Driving Case
At the same time Sylvester is awaiting trial, Doby is facing criminal charges stemming from a separate 2025 crash in which prosecutors say she drove drunk and rear-ended a work-release transport van, injuring another person.
If convicted, the charge would represent her second drunk-driving offense.
However, court records show Doby’s earlier 2022 OWI case — the arrest that led to the hospital encounter with Sylvester — never resulted in an OWI conviction.
Instead, then-City of Kenosha prosecutor Christine Genthner amended the charge to a non-criminal traffic violation, allowing Doby to plead to failure to maintain control of a vehicle to avoid an accident.
The unusual plea agreement resulted in only a forfeiture and demerit points rather than the license revocation and other penalties typically associated with an OWI conviction.
Genthner, who has since retired from the City Attorney’s Office, has never publicly explained the decision. At the time, critics alleged the deal was intended to discourage Doby from filing a lawsuit against the city.
That theory ultimately proved incorrect.
Doby filed her federal civil-rights lawsuit anyway on the final day allowed by law.
City Potentially Facing Large Liability
If the case ultimately proceeds to trial and a jury finds in Doby’s favor, the City of Kenosha could be responsible for paying damages because Sylvester was acting as a police officer at the time of the alleged assault.
For now, the lawsuit remains active — though it came dangerously close to being dismissed just over a week ago after the plaintiff’s attorney failed to meet a court-ordered deadline for months.
3 Responses
Man I wish you could bet on Kalshi who the next article is going to be about. I see a familiar face in the jail bookings. I have a feeling a new story is coming…….
oh for sure…… Kalshi, Id like to make a wager that its a KUSD employee
Nobody is assaulting this lady.