As the U.S. Department of Justice prepares to monitor Wyoming’s general election operations Tuesday, it is appointing Secretary of State Chuck Gray’s former No. 2 office staffer to oversee the job.
Jesse Naiman, of Cheyenne, went from working as a senior assistant in the Wyoming Attorney General’s Office to being deputy secretary of state in late 2022.
That was when 80% of the secretary of state executive team quit in the days after Gray’s election to the position.
Naiman’s predecessor, Karen Wheeler, who worked in the office for 37 years, was part of the exodus.
It’s unclear how long Naiman remained with Gray’s office. The Albany County Republican Party billed him as the deputy SOS as recently as August 2025.
Naiman's name and SOS email address appear July and August 2025 exchanges that George Powers, a critic of and litigant against Gray, received as public records.
The heavily redacted emails show that Naiman edited a letter to the DOJ in July 2025, when Gray's office was reportedly giving the federal agency an already-public version of Wyoming's voter rolls.
Naiman is copied on a later, August email in which Gray's policy chief Joe Rubino sought input from the state attorney general.
In August 2025, Gray's office gave the DOJ a more expansive version of the voter rolls, containing sensitive information like driver's license numbers and partial Social Security numbers.
In late 2025 or early 2026, Naiman went to work for the U.S. Attorney for Wyoming, a post helmed by the former, briefly serving state Sen. Darin Smith.
Naiman has been prosecuting federal cases since at least April of this year, court records show.
He did not immediately return a voicemail request for comment.
Smith’s office announced Thursday that Naiman will lead the efforts in coordination with the DOJ’s “nationwide election monitoring program” for the election Tuesday.
“Ensuring election integrity, supporting free and fair elections, and protecting the right to vote for U.S. citizens across Wyoming is a key priority of our office,” said Smith in the statement.
Naiman is tasked with overseeing election day complaints, the statement says.
“Working in consultation with Justice Department Headquarters in Washington, D.C., his responsibilities include addressing voting rights concerns, election fraud allegations, and threats of violence directed at election officials or staff,” says the statement.
It notes that DOJ has deployed election monitors since the passage of the Voting Rights Act of 1965.
“This long-standing initiative serves to deter and combat poll intimidation, discrimination, fraudulent voting practices, and threats targeting poll workers and election personnel,” the statement says.
Monitoring
DOJ election monitors visited Laramie County polling sites Aug. 18, to the surprise and consternation of Laramie County Clerk Debra Lee, who cast the operation as disruptive and ill-noticed.
Gov. Mark Gordon also raised the alarm, casting the incident as federal overreach.
Lee sought a legal opinion from Wyoming Attorney General Keith Kautz on the monitors’ authority to occupy election spaces.
Kautz concluded that state law bars them from the operation, absent an agreement, court order, or consent decree. Because disrupting elections is a crime, the sheriff could also get involved if needed, Kautz noted.
Lee announced Wednesday that in light of Kautz’s opinion, the federal monitors will be barred from coming within 100 yards of the polls. She said they’ve agreed to that, and to only interview voters who consent to be interviewed.
This story has been updated to reference public documents from George Powers.
Clair McFarland can be reached at clair@cowboystatedaily.com.
