Confidential report criticizes fired Dubuque County prosecutor

By: - October 17, 2022 11:05 am

A confidential investigation into former Dubuque County prosecutor Richard Kirkendall (inset) concluded the lawyer was “hostile” to his boss, calling him a liar and a “monumental jerk” before being fired for insubordination. (Photo illustration by Clark Kauffman/Iowa Capital Dispatch. Inset photo from Facebook video)

A fired Dubuque County prosecutor’s claim that he was cleared of wrongdoing appears to be contradicted by a confidential investigator’s report detailing the lawyer’s conduct.

Former Assistant Dubuque County Attorney Richard Kirkendall, who is now running for county attorney, has stated publicly that the county fired him in March for insubordination. But he has also suggested that the firing was politically motivated and that an investigation into his conduct cleared him of wrongdoing.

However, the investigator’s confidential report to the county, written five months ago and recently obtained by the Iowa Capital Dispatch, details the manner in which Kirkendall emailed colleagues about an alleged inappropriate relationship between the Dubuque County attorney, C.J. May, and the county’s victim witness coordinator.

In the email, Kirkendall acknowledged that such a relationship between May and the victim witness coordinator, Ali Newsom, may not exist. But he went on to criticize May for it and suggested it was a potential liability for the county.

Kirkendall’s email could prove costly to the county. Lawyers for Newsom recently filed a claim with the county seeking $750,000.

Kirkendall now hopes to replace his former boss, May, as Dubuque County’s top law enforcement official. May was defeated in the primary election, and Kirkendall is now running as an independent against Democrat Sam Wooden and Republican Scott Nelson.

The investigator’s report details several instances in which Kirkendall was hostile and argumentative in his dealings with May, calling his boss incompetent, a liar and a tyrant.

The investigation into Kirkendall’s conduct was conducted by attorney Amy Reasner at the request of the county. The 16-page report states that it is to be kept confidential due to attorney-client privilege, with the client being the county.

Kirkendall: The ‘public deserves’ to know findings

In her report, Reasner is critical of Kirkendall’s attitude and actions in the county attorney’s office but says Newsom’s complaint alleging he had harassed her was not substantiated.

In her report, Reasner states that the Iowa Civil Rights Act and county policy protects certain classes of people, such as women, from harassment, but noted there’s no evidence Kirkendall acted the way he did because Newsom is a woman. In addition, the county doesn’t have anti-bullying or “respect in the workplace” polices that might apply to the situation, Reasner stated.

Kirkendall said Friday he has not seen Reasner’s report and cannot comment on it without seeing it in its entirety.

However, in a May 11 Facebook video, Kirkendall announced the completion of the investigation and suggested the report, which he hadn’t seen, had cleared him of any wrongdoing.

“That investigation has not turned up any wrongdoing by me,” Kirkendall says in the video. “I do have questions about the investigation still. I have not been able to see the investigator’s report. Dubuque County is refusing to release that. I hope that it does become public at some point. I think there’s probably a lot of interesting information in there about how the county attorney’s office operates. I think the public deserves to know that.”

Kirkendall said on Friday that the county still has not shared the report with him.

Kirkendall called boss a liar, a jerk and a tyrant

Part of Reasner’s investigation centered on an email Kirkendall sent to May on March 18 and then forwarded to six fellow assistant county attorneys, writing, “In case this is my last email … it’s been a pleasure working with all of you.”

In the email, Reasner said, Kirkendall “launched into an allegation that Mr. May’s ‘relationship’ with Ms. Newsom appears to be inappropriate and exposes the county to liability.” In the email, Kirkendall also provided his colleagues with his own “scathing review” of Newsom’s work performance, Reasner noted. “Mr. Kirkendall also denigrates Mr. May’s workload and then calls him a liar,” Reasner added.

In the email, Kirkendall wrote to May:

“Your relationship with Ali is a liability for the county, too. Even though you are – as you say – her supervisor, you fraternize with her regularly – who else from the office has gone on your boat with you alone? – and you text her at all hours of the day and night … If Ali were to bring a complaint of sexual harassment against you and the county would anyone be surprised? Whatever the truth is, the relationship appears to be inappropriate. You will splutter and take umbrage, but you lie – you lied just this week when I confronted you about the immature texting about me, witnessed by multiple independent witnesses and which Ali was kind enough to confirm.”

The “immature texting” cited by Kirkendall appears to be a reference to Newsom texting May an emoji of a person vomiting. It was allegedly sent during a work meeting immediately after someone had paid Kirkendall a compliment.

In his March 18 email, Kirkendall went on to tell May, “I will not be at your meeting on Monday – I am much too busy,” and he called the planned meeting a “waste of time.” He ended the email by telling his boss, “You should save your harassment for those who still care to kowtow to you.”

Report: Kirkendall taped discussions with May 

Reasner’s report states that Kirkendall tape-recorded some of his meetings with May.

One of the tapes, in Kirkendall’s view, documents an instance in which May unfairly accused him of not liking Newsom because he had personal feelings for her predecessor. In her report, Reasner said she listened to the tapes three times and found that “Mr. May said no such thing directly.” Reasner stated that “Kirkendall hears the implication only because is looking for the offense.”

In one meeting, Reasner reported, Kirkendall called May “a monumental jerk” and objected to May’s request that he be copied on certain emails. She reported that it is “patently obvious” from the recordings that Kirkendall “refused to admit that if Mr. May wants to be copied on emails … then that’s what Mr. Kirkendall needs to do … It is also patently obvious that, over time, Mr. Kirkendall’s communications with Mr. May became increasingly hostile and rude.”

As part of her investigation, Reasner looked not only at Newsom’s harassment complaint, but at Kirkendall’s subsequent claim that May had orchestrated Newsom’s complaint, that it was politically motivated, and that the investigation into his conduct was in retaliation for his announcement that he intended to run for county attorney. Reasner found those complaints were not substantiated.

Kirkendall had served as an assistant county attorney from 2018 until he was placed on administrative leave, and then fired, in March. He announced his being placed on leave to the media and said at the time it was in retaliation for his decision to seek election as county attorney. May denied the claim that Kirkendall was fired for political reasons, KCRG reported.

Kirkendall asked bargaining unit for ‘solidarity’

At some point after he was placed on leave, Kirkendall sent a text message to his former colleagues in the prosecutor’s office, saying, “I’m not sorry about anything I’ve said to CJ, and frankly more and worse needs to be said. It is not a good feeling getting walked out of the building. 0/10 would not recommend, but it is still better than giving in to a petty tyrant.”

While facing disciplinary action, Kirkendall also sent an email to members of his bargaining unit.

In that email, he stated “one of you decided to print out my last email and give it to Ali.” He went on to write, “As a member of this union, I ask for solidarity always.” He told the union members, “If you do have anything negative to say about my workplace performance, I hope that you feel comfortable saying it directly to me.”

Reasner made note of that email in her report, adding that one bargaining unit member said they felt it was an attempt at intimidation and another said they wished Kirkendall had never sent it.

The conflict between Kirkendall and his boss, May, dates back at least to November 2020, when the two exchanged emails over what May considered Kirkendall’s “insolent” behavior.

“You take issue with insolence,” Kirkendall wrote to May. “I take issue with rank incompetence … I take issue with a management style that prioritizes your ease over the well-being of your employees.”

In May 2021, Kirkendall filed a grievance against May, alleging the county attorney had created a hostile work environment. As part of that grievance, Kirkendall asked that May deliver to him a written apology “for past disrespect.”

In a Facebook post after the report was shared with the county, Kirkendall posted another critique of May, stating, “CJ May has squandered the human capital in the county attorney’s office. The toxicity and dysfunction in the office today are his legacy.”

County employee was working a second job

Reasner’s report also sheds light on why Newsom’s predecessor, Caitlin Vrotsos, left the job of victim-witness coordinator.

The report indicates May was unhappy that Vrotsos was working a second job as an instructor at the University of Dubuque. The university job took Vrotsos out of the county attorney’s office during the middle of the workday and May objected to the arrangement.

“These are legitimate personnel concerns about expending county taxpayer dollars,” Reasner wrote in her report.

May did not return several calls to his office over the past two weeks. Darvin Curtiss, a Dubuque County lawyer who asked Reasner to perform the investigation for the county, declined to comment on the matter. Iowa Capital Dispatch was unable to reach Newsom.

Newsom’s $750,000 claim against the county was made public on Aug. 29, just before the Dubuque County Board of Supervisors went into a closed session to discuss legal matters.

While the board was still in open session, County Supervisor Ann McDonough announced the county had received a note “from a law firm in Minnesota representing Ali Newsom who has made a $750,000 claim” against the county.



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Clark Kauffman
Clark Kauffman

Deputy Editor Clark Kauffman has worked during the past 30 years as both an investigative reporter and editorial writer at two of Iowa’s largest newspapers, the Des Moines Register and the Quad-City Times. He has won numerous state and national awards for reporting and editorial writing.