Sheriff’s Deputy Is Again Sending Controversial Emails To Politicians

Milwaukee County Sheriff’s Office vehicle in Sherman Park. Photo by Jeramey Jannene.

A Milwaukee County Sheriff‘s Office (MCSO) deputy who has already been suspended once for emails he sent to Wisconsin elected officials has once again sent officials a controversial message.

This time, David Willoughby emailed elected officials asking about transgender people using bathrooms that correspond to their gender identity and stating that he thinks it is a “major safety issue.”

This is not the first time Willoughby has courted controversy. In 2012, Willoughby was arrested while protesting at a rally for then-City of Milwaukee Mayor Tom Barrett, who was running against then-Gov. Scott Walker in the gubernatorial recall election.

In 2021, he sent an email, signed “Deputy Willoughby Milwaukee County Sheriff’s Office,” to dozens of local politicians. It included a tweet by U.S. Rep. Rashida Tlaib (D-MI) criticizing law enforcement and asked them to indicate whether they agree or disagree.

For sending that email, he was suspended by the Milwaukee County Sheriff’s Office. Publicly available records from the county’s Personnel Review Board indicate he appealed his suspension to the Wisconsin Employment Relations Commission. He settled his disciplinary case with the county in 2022 and was not discharged from MCSO service. Details of the settlement with the county were not included in personnel review board minutes from March 8, 2022 that reference the settlement of the matter.

Sup. Ryan Clancy, an outspoken critic of law enforcement, provided Urban Milwaukee with a string of emails from Willoughby and himself, showing that on July 27, Willoughby emailed the entire county board attacking the Milwaukee County Parks policy of allowing transgender people to use the bathroom that corresponds to their gender identity and it “is a major safety issue.”

Willoughby was critical of his employer’s alleged decision on how to enforce the policy. “According to the Milwaukee County Sheriff’s Office; [sic] Command Staff, ‘We will not arrest transgendered people merely for their choice of restroom or locker room,'” wrote the deputy.

Willoughby did not sign the email as a sheriff’s deputy this time and, as he had in 2021, sent the emails from a personal account. He defended his previous actions in 2021 by saying they were done on his own time and with his own email account, as reported by Wisconsin Right Now. The head of the sheriff’s deputies union said then that Willoughby was accused of breaking MCSO policy on prohibited speech and expression.

The MCSO policy manual includes a section on “Prohibited Speech, Expression and Conduct” that forbids deputies from engaging in expression “pursuant to official duty” that can “compromise or damage” the MCSO. It also prohibits speech or expression that “while not made pursuant to an official duty, is significantly linked to, or related to, the Milwaukee County Sheriff’s Office and tends to compromise or damage the mission, function, reputation or professionalism” of the agency. It also prohibits any speech that “could reasonably be foreseen as having a negative impact on the credibility of the employee as a witness.” The manual uses “expressions that glorify… unlawful discrimination” as an example of such discrediting speech.

When Willoughby sent his latest emails, it wasn’t just local politicians whose attention he sought. Willoughby also included conservative media members Dan O’Donnell, Vicki McKenna and Mark Belling, as well as the conservative media outlet Wisconsin Right Now and a general email for the TV news station TMJ4.

Clancy forwarded the email to Sheriff Denita Ball the next day. Molly Zillig, MCSO Chief Legal and Compliance Officer, responded. “Be assured that the Sheriff takes this very seriously. This matter is under investigation but as you are aware, pending internal employee matters are confidential. We will be in contact with you in the very near future regarding your concerns,” wrote Zillig.

When reached for comment, James Burnett, director of public affairs and acting chief of staff for MCSO, told Urban Milwaukee that he cannot comment on confidential personnel matters.

In his emails to MCSO, Clancy stated that he has flagged messages from Willoughby in the past and that his concerns about the deputy’s “abusive and harmful rhetoric have gone unanswered.”

“Everyone deserves a work environment free of this sort of prejudice and bias,” Clancy said in an email to MCSO, “but this is much more alarming if the deputy in question has the ability to act on these biases within his professional capacity.”

Willoughby did not respond to a request for comment by the time of publication.