KENOSHA, Wis. — Kenosha Alderman Anthony Kennedy, a liberal Democrat who has held office for nearly two decades, invoked his elected title in a direct email to Liberal Judge Jason Rossell (D), seeking favorable consideration for longtime friend and fellow Democrat Andrew Allen “Andy” Berg, 48, of Kenosha. Berg, also known as “Sgt. Hard,” faces two separate drug-related prosecutions, including a newer case charging 22 criminal counts while he was already on bail, yet Kennedy’s appeal drew a procedural reminder and a thank-you from Rossell.

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The October 22 correspondence is now part of the public record in Berg’s newer felony case. That same day, Rossell signed paperwork recusing himself because of familiarity with Berg arising from his time as chief judge—an explanation that raises questions about his earlier involvement in Berg’s criminal proceedings.

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Kennedy sent his email at 6:06 a.m. from a personal Yahoo account and copied Clerk of Circuit Court Rebecca Matoska-Mentink. He signed the message with his name, his position as “10th District Alderman,” and the slogan, “SERVING THE COMMUNITY… WORKING FOR YOU!”

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That signature placed the standing of Kennedy’s public office behind his personal appeal. He approached the judge as a longtime elected official advocating for a political friend facing serious criminal allegations.

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“I am writing to you on behalf of Andy Berg,” Kennedy wrote. “I have known Andy for nearly 15 years, during which time I have considered him a friend, a colleague, a dedicated elected official, and an outstanding community advocate.”

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Kennedy described working alongside Berg on initiatives involving veterans, food pantries, pumpkin donations to schoolchildren, and community fundraising. He said he had “deeply admired Andy” and had been proud to call him a friend and County Board colleague.

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The alderman acknowledged that his assessment of Berg had changed. He wrote that “the person Andy has become is far different from the individual I once knew,” adding that he did not intend to excuse Berg’s behavior or the charges.

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Nevertheless, Kennedy urged consideration of Berg’s potential for rehabilitation. He described “a redemptive journey back to his better nature” and said counseling and guidance could help him become productive again.

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“It is my fervent prayer that our community will extend the same support to him in his time of need as he has provided to others in theirs,” Kennedy wrote. He concluded by thanking Rossell for considering his reflections.

The timing is central to the concern. Character letters emphasizing a defendant’s good qualities and rehabilitation are ordinarily associated with sentencing, when a judge weighs punishment after a conviction, rather than the beginning of a contested prosecution.

Berg’s newer case had been filed just over a month before Kennedy’s email. No conviction or sentencing in that case prompted the alderman’s appeal, and the allegations had not been tested at trial.

Several political and courthouse insiders who spoke with KCE said Kennedy knows better. They viewed the early intervention, combined with his use of his aldermanic title, as an attempt to influence the judge’s treatment of his longtime friend.

The email did not expressly request dismissal of charges or Berg’s release. It nevertheless delivered an elected official’s favorable assessment directly to the judge, with neither the prosecutor nor defense attorney shown among its recipients.

Kennedy, a self-described “bleeding-heart liberal,” made his appeal amid allegations extending well beyond an isolated incident. Berg’s newer prosecution followed an earlier case involving 13 felony charges, including drug-delivery offenses and firearm straw purchasing.

As KCE reported September 17, the newer case brought 22 counts, including methamphetamine and cocaine delivery, prescription-drug offenses, maintaining a drug trafficking place, and 11 felony bail-jumping counts. Prosecutors argued that Berg had returned to serious drug activity while already on bail and requested $300,000 cash bail.

Kenosha County Court Commissioner Daniel “Catch & Release” Kellum instead kept cash bail at $75,000. The newer bail-jumping allegations stemmed from conduct prosecutors said violated conditions imposed in the earlier prosecution.

Berg’s repeated arrests have also imposed substantial financial consequences on his family. His father previously posted $75,000 cash bail in the earlier case, committing a significant sum while the criminal allegations remained unresolved.

According to KCE’s reporting, Kennedy has also appeared at traffic stops involving friends facing arrest and attempted to throw his political weight around. His intervention for Berg raises a similar concern about the use of public standing to seek favorable treatment for personal associates.

Rossell replied at 9:08 a.m., addressing Kennedy as “Alderman Kennedy.” His response concentrated on the administrative work created when someone emails a judge about a pending case.

“By emailing, instead of using mail, the Court system employees have to then receive the email from the court, scan, file and then provide copies to the parties in the case,” Rossell wrote. He instructed Kennedy to submit future case-specific correspondence through the clerk’s office or mail it to the courthouse.

Making the exchange part of the court record was the appropriate step. Political and courthouse insiders who discussed the matter with KCE nevertheless believed Kennedy should have received a firmer response about directly approaching the judge on behalf of a defendant.

Rossell instead closed with, “Thank you for your continued public service.” In KCE’s view, that courtesy reflected political deference when the circumstances called for a clear statement that an alderman’s friendship with a defendant carries no special weight.

Rossell’s decision to step aside raises an additional and potentially more consequential issue. He had already exercised judicial authority in Berg’s earlier prosecution before identifying familiarity with Berg as grounds for recusal in the newer case.

In January, KCE reported that Rossell declined to shield alleged victims’ identities, including a minor’s, leaving those identities publicly accessible. That was a consequential judicial decision involving the privacy of people identified as victims in Berg’s earlier case.

The October 22 assignment paperwork offered a brief explanation for his departure from the newer case: “Judge Rossell recuses as he is familiar with the DE due to Judge’s time as Chief Judge of District 2.” It identified disqualification under Wisconsin Statute 757.19(2)(g).

That explanation demands more detail. If the same familiarity existed when Rossell made the earlier ruling affecting alleged victims’ identities, why did it require recusal now but apparently did not prevent him from acting then?

Wisconsin’s judicial conduct rules require recusal when the circumstances known to a judge would cause reasonable, informed observers to question the judge’s impartiality. Whether that requirement applied earlier depends on the nature and timing of the circumstances, along with any disclosure or waiver.

If disqualifying circumstances were already present, Rossell should have addressed them before making consequential rulings. His later recusal raises a serious potential judicial-conduct issue, although the available documents do not establish that misconduct has been formally found.

The supplied assignment form does not explain the underlying familiarity, when Rossell recognized it as disqualifying, or whether it affected his earlier involvement. It also does not identify Kennedy’s email as the reason for recusal, so the fact that both occurred October 22 does not establish that one caused the other.

The paperwork states that a tab was pulled for Branch 4, pending approval from District 2. It lists a December 4 status conference as the next scheduled proceeding.

Kennedy’s decision to invoke his aldermanic title for a political friend is documented in his own email. Rossell’s explanation for stepping aside now requires the same transparency: the public deserves to know why familiarity with Berg required recusal after the judge had already participated in his earlier prosecution.