Prosecutors’ Relationship Raised in Alaska Misconduct Saga

The Justice Department acknowledged a romance between Alaska federal prosecutors but argued it doesn’t merit retrying a case that defense attorneys claim was mishandled, according to new filings in the saga over a judge’s misconduct that rocked the state’s legal community.

The public admission is just the latest fallout from US District Judge Joshua Kindred’s resignation a year ago over findings that he created a hostile workplace for his law clerks and had inappropriate relationships with female attorneys, including a federal prosecutor.

That matter has prompted defense attorneys with cases before Kindred and involving certain prosecutors to raise potential conflicts of interest. At least one retrial has been ordered.

In a June 30 filing,DOJ attorneys noted the relationship between the former criminal chief in Anchorage, Andrew James Klugman, and Karen Vandergaw, whom Klugman previously supervised.

Klugman had been the attorney of record in a case against Nathan Michael Keays, who was convicted in April 2024 of wire fraud and money laundering. Vandergaw is at the heart of dozens of defense motions related to the controversy seeking to overturn convictions or hold new trials.

Vandergaw was found this year by the Justice Department’s professional responsibility office to have engaged in “intentional professional misconduct” when she continued arguing cases in Kindred’s courtroom while sending him explicit photos of herself. She later said that she felt coerced to do so.

Keays is seeking a new trial, pointing to misconduct by Kindred and prosecutors involved.

In court papers, DOJ attorney Steven Clymer—assigned to Anchorage after the Kindred scandal broke—argued that Vandergaw only worked on a preliminary stage of Keays’ case, and that Klugman’s relationship with Vandergaw didn’t require the judge’s recusal.

“Granting Keays the windfall of a new trial is not a proper response to either Kindred’s wrongdoing or evidence that these AUSAs were deceitful,” the filing reads. “Simply put, Keays has not shown that Kindred had an obligation to recuse or that he (Keays) otherwise is entitled to a new trial.”

Klugman and Vandergaw are on administrative leave while DOJ evaluates the situation for disciplinary conduct, the agency said in the filing.

Klugman and Vandergaw didn’t immediately return requests for comment. A spokesperson for the Anchorage US Attorney’s Office declined to comment beyond the contents of the court filings.

Relationship Timeline

The court filings paint a picture of the timeline of the relationship between Vandergaw, who was married, and Klugman, her former supervisor who lived with his-then fiancee.

They said in a 2024 interview that their relationship was platonic until late December 2023 after moving in together. and after Klugman was no longer the criminal chief, according to the court filings.

However, the Justice Department told the court that concerns the pair had an undisclosed romantic relationship were raised to another leader at the office as early as July 2023. Klugman denied the relationship to US Attorney Lane Tucker later that summer, according to the filing.

The two took five out-of-town trips together, some work-related, beginning in the summer of 2022, including one trip to Seattle where they stayed in the same hotel suite but claimed to have slept in separate beds, the government said.

Both ended their respective relationships with other people shortly after the September 2023 Seattle trip, and vacationed together in a “studio condo” in Hawaii at the end of that year. In December 2023, just after Klugman’s term as criminal chief ended, Vandergaw moved in with him, according to the filings.

Tucker and her top deputy both said that Klugman pushed for Vandergaw to be promoted in 2023 while he was criminal chief, which Klugman denies, according to court filings.

Tucker, who stepped down as US attorney earlier in the Trump administration, said in a deposition that Vandergaw lacked credibility and that Klugman was “untruthful.”

The deposition interview was conducted after Tucker faced scrutiny of her own in response to the Kindred allegations. DOJ settled a whistleblower complaint alleging she was part of a US attorney’s office leadership team that retaliated against Kindred’s former law clerk.

New Trials

The request represents the latest effort by defense lawyers to have new trials ordered. Last year, a federal judge ordered a new trial for an Alaska man convicted of cyberstalking in Kindred’s courtroom, on judicial misconduct grounds over Vandergaw’s involvement in the prosecution.

Defenders also requested a new trial last month for a former nurse convicted of illegally prescribing opioids that led to the deaths of multiple people, citing the judge’s relationship with Vandergaw.

Keays noted in his new trial request that Kindred had testified before the Ninth Circuit’s Judicial Council about the allegations of misconduct during his trial.

“With a judge who perjured himself mid-trial and involvement by two Assistant U.S. Attorneys who are described as dishonest, both the appearance and reality of a fair trial and the impartial administration of justice are lost,” Keays’ attorneys wrote in a June 26 motion.

The case is USA v. Nathan Keays, D. Alaska, No. 3:20-cr-00085, 6/30/25