A former Anchorage police officer convicted of fraud is seeking a new trial, arguing he was treated unfairly because of a secret relationship between two federal prosecutors in the case, including one at the center of a scandal that ousted the presiding judge.
Former U.S. District Court Judge Joshua Kindred resigned in July of 2024, days before the release of a report by the Ninth Circuit Judicial Council detailing his sexualized relationships with two prosecutors in the Alaska U.S. Attorney’s Office, including one who sent him nude photos.
At the U.S. Attorney’s Office, which prosecutes some of the highest-level crimes in the state, the report triggered a review of dozens of cases for conflicts of interest. Defense attorneys have argued, at least once successfully, that Kindred’s close relationships with the prosecutors meant he was susceptible to bias against their clients.
Now, ex-Anchorage cop Nathan Keays’ motion for a new trial points to professional misconduct by the former head of criminal prosecutions in the U.S. Attorney’s Office, who had not previously been tied to the scandal.
According to Keays’ motion for a new trial filed this June, one of the main prosecutors in his case – U.S. Attorney’s Office Criminal Division Chief James Klugman – had engaged in a secret, romantic relationship with Assistant U.S. Attorney Karen Vandergaw, the same prosecutor who had previously sent Kindred nude photos and who also worked on the Keays case in a limited role.
Several months before his resignation, Kindred had presided over Keays’ trial. Keays and a friend from high school who worked at ConocoPhillips were charged with embezzling more than $3 million from the oil company. A jury convicted Keays on wire fraud and money laundering charges in April 2024.
The U.S. Attorney’s Office does not dispute that Klugman and Vandergaw were in an inappropriate relationship, according to a filing in response to the motion for a new trial.
In the filing, the federal government’s top attorneys in Alaska describe Klugman and Vandergaw – their own prosecutors – as dishonest.
Klugman did not respond to a request for comment for this story. Neither Kindred or Vandergaw could be reached for comment.
The prosecutors’ 204-page filing in the Keays case details what Department of Justice investigators learned about the relationship between Klugman and Vandergaw.
The filing says Klugman and Vandergaw had traveled together on official business four times, including to an arson investigation training in Huntsville, Alabama in July of 2023.
It was around that time that a senior official in the U.S. Attorney’s Office heard rumors that Klugman and Vandergaw were involved in a “romantic or unusually close personal relationship,” the prosecutors’ filing says. When then-U.S. Attorney S. Lane Tucker asked Klugman if he was in a romantic relationship with Vandergaw, he denied it.
But Vandergaw also went with Klugman when he flew to Seattle to argue in an appeal in September of 2023, even though Vandergaw wasn’t working on the case, according to transcripts of interviews between Klugman and the Department of Justice’s Office of Professional Responsibility, which are included in the prosecutors’ filing.
Klugman admitted he and Vandergaw shared a hotel suite in Seattle on that trip, but he said they slept in different beds.
One of the investigators said it seemed odd that Vandergaw took time away from her family and work to travel with Klugman, since she could’ve watched the argument online.
“No, I don't find that strange at all,” Klugman replied, according to the transcript. “I mean watching something in person is very different than watching it on YouTube.”
Back in Anchorage, Klugman broke up with his fiancé, who had to find a new place to live, and Vandergaw told her husband she wanted to end their marriage, the prosecutors’ filing says.
According to the filings, Vandergaw had also initially lied to the Department of Justice investigators when they asked her if she had any improper interactions with Judge Kindred. Later, after the separate Ninth Circuit Judicial Council report came out, the investigators circled back to Vandergaw, who admitted she had exchanged nude photos with Kindred, saying she lied because she was afraid of Kindred.
Tucker, the U.S. Attorney at the time, later told the investigators she thought both Vandergaw and Klugman had been dishonest.
“I wouldn't trust her to do anything. I don’t think she’s honest,” Tucker said of Vandergaw, according to the filing.
“Tucker opined that Klugman is ‘not truthful . . . and does not have candor,’” the filing says.
Attorneys representing Keays, the former police officer convicted of fraud, say the prosecutors’ dishonesty – along with Kindred’s lies under oath before the Ninth Circuit Judicial Council and his compromised position while still on the bench – led to an unfair trial for Keays.
“A new trial is a reasonable, middle-ground approach that protects Mr. Keays’ constitutional rights to a fair trial and impartial judge, the public’s confidence in the judicial system, and the government’s discretion in its prosecutions,” Keays’ attorney wrote.
That’s where the U.S. Attorney’s Office disagrees.
“There is no evidence that Kindred, Vandergaw, or Klugman were dishonest in
connection with the prosecution of Keays or that any falsehoods prejudiced Keays or
influenced his case,” the federal prosecutors’ filing says.
Klugman and Vandergaw have since gotten engaged and were on administrative leave, facing possible disciplinary action, at the time of the prosecutors’ filing in late June.
Whether Keays will get a new trial remains to be seen.
Another defendant convicted in federal court, former nurse practitioner Jessica Spayd, is also asking for a new trial related to Judge Kindred’s misconduct. In 2023, Kindred sentenced Spayd to 30 years in prison after she was convicted of illegally over-prescribing opioids through her Eagle River pain clinic, resulting in the deaths of five people, according to federal prosecutors.
