Skyler/Skylar Ittner sentenced for assaulting Sheriff at 2024 Last Chance Stampede

A man identified in court filings as Skyler Ittner and in courtroom captions as Skylar Dexter Ittner pleaded guilty to felony criminal endangerment and was given a three-year deferred sentence by Lewis and Clark County District Court Judge Kathy Seeley on Feb. 26, 2026. The hearing took place in Helena; Seeley accepted the plea and ordered no early termination of the deferred sentence.

Court documents filed in the case describe the 2024 altercation at the Last Chance Stampede at the Lewis and Clark County fairgrounds as beginning when Ittner was arguing with a fair vendor and refused repeated requests to leave. According to those documents, Sheriff Leo Dutton approached and asked Ittner to leave; when Ittner refused the sheriff used his body to push Ittner away from the booth, Ittner stepped into the sheriff, and both men went to the ground. Deputies moved to detain Ittner, and while Sheriff Dutton was on the ground Ittner allegedly punched him, producing noticeable swelling.

The case was originally filed as a felony assault on a peace officer. Prosecutors took that charge to trial in May of last year, and that trial ended in a hung jury. Ahead of the Feb. 26 hearing prosecutors amended the charge to felony criminal endangerment; Ittner entered a guilty plea to the amended charge and was sentenced under the deferred disposition.

Judge Seeley imposed a three-year deferred sentence with conditions that include completing all probation requirements, paying court fees, and remaining law-abiding. The deferred sentence carries an explicit no-early-termination term. If Ittner fails to meet those conditions, the judge may vacate the deferred disposition and sentence him on the felony criminal endangerment charge, which carries statutory exposure of up to 10 years in state prison and a $50,000 fine.

Courtroom photographs from Feb. 26 show the defendant seated before Judge Kathy Seeley for the change-of-plea and sentencing hearing, and a video of the plea change and sentencing was recorded at the proceeding. The record available in court filings lists Sheriff Leo Dutton as the law-enforcement victim and records the swelling to the sheriff described in the charging materials.

The disposition leaves prosecutors the option to pursue incarceration if the deferred sentence is revoked, while the deferred term requires ongoing supervision and court fees for three years. The differing spellings of the defendant’s first name in court captions and filings appear in the record and should be resolved in official court documents for any future enforcement or appeal.