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News
 May 27, 2026

Roosevelt County Candidate's Eligibility For Sheriff Position Questioned, Complaint Filed in District Court

This story is credited to the Northern Plains Independent a weekly newspaper based out of Wolf Point, Montana. 

https://www.northernplainsindependent.com/

By Darla Downs and Bill Vander Weele

One of the two candidates seeking the position of Roosevelt County sheriff may not be eligible to hold the office, according to information gathered by the Northern Plains Independent.

Wesley Headdress’ qualifications for holding the office is in question because he was convicted of felony theft in Fort Peck tribal court in 2020. Because there are only two candidates for county sheriff, the race isn’t part of the June primary election. The office will be decided during the general election in November.

According to Montana Code Annotated 7-32-2133, a person is not eligible for the position of sheriff at the time of election or appointment unless the individual has not been convicted of a crime for which the person could have been imprisoned in a federal or state penitentiary.

Headdress signed a declaration for nomination and oath of candidacy form with the Roosevelt County Clerk and Recorder’s office on Feb. 19. The form includes a signature by him that he meets the qualifications for the sheriff’s position.

Roosevelt County resident and Northern Plains Independent publisher Darla Downs filed a complaint against Headdress in District Court on Friday, May 22, requesting that Headdress be declared ineligible to be elected sheriff, the election administrator remove Headdress from the ballot and that the election administrator disregard any votes cast for Headdress for sheriff.

Headdress said on social media on Saturday that he was withdrawing from the election and that he has applied for Wolf Point’s athletic director position.

Wolf Point Superintendent of Schools Dr. David Perkins told this newspaper that there are four or five applicants for the athletic director position and that there is no concrete timetable for hiring a new athletic director.

The felony theft charge, according to documents filed on March 13, 2019, in the Fort Peck Assiniboine and Sioux Tribes Tribal Court, occurred when Headdress advised the Fort Peck Tribal Council that he was going to auction off ceremonial guns purchased for the Veterans Affairs Department using a Chinese auction. During this time, Headdress subsequently sold eight guns purchased by Tribal Resolution #26-2819-2013-08 to various members of the community, but never deposited the money into any Fort Peck Tribal account and kept the money for himself. The guns were purchased for $12,799.92 from Scheels Sports in Billings and the Fort Peck Tribes issued a payment invoice. Headdress sold the rifles and the total amount of funds he kept without depositing in the Fort Peck Tribes account was $8,400.

On March 13, 2020, Headdress was adjudged guilty of violating 7.320 of the comprehensive code of justice. The sentence was 90 days flat suspended for 90 days of probation and he was ordered to pay restitution in the amount of $8,400 by June 11, 2020.

In addition, Montana Code Annotated reads that a person is not eligible to hold the sheriff’s position unless the individual is eligible to receive and disseminate criminal justice information through the Criminal Justice Information Network. An elected or appointed sheriff who fails to obtain access to the criminal justice information network forfeits office for failure to satisfactorily meet the qualifications required of a sheriff.

Montana’s Criminal Justice Information Network’s guidelines note that a security waiver is required whenever a terminal agency discovers an individual has a felony arrest, even if the disposition is missing, deferred or dismissed, or a felony conviction, even if the disposition is missing, deferred or dismissed, or has three or more misdemeanor convictions in the last 10 years excluding dismissed records.

Jason Baker is the other filed candidate for Roosevelt County sheriff. Long-time sheriff Jason Frederick announced earlier this year that he would not seek re-election.

Link to District Court Complaint Affidavit

Link to Criminal Complaint

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