AM 890 and Serving the Kenai Peninsula
Play Live Radio
Next Up:
0:00 0:00
Available On Air Stations

Harold Gregory sentenced to 33 years for murder of girlfriend

Krysti Shallenberger
Crooked Creek

On Tuesday, May 23, Bethel Superior Court Judge Nathaniel Peters sentenced 33-year-old Harold Gregory of Crooked Creek to 45 years with 12 years suspended and 33 years to serve.

“The Harold Gregory case is a homicide that occurred in August of 2019. And Harold Gregory murdered his girlfriend, Cheryl Sakar. In the home that they shared in Crooked Creek,” Prosecutor Bailey Woolfstead said.

Woolfstead is the Assistant Attorney General of the Office of Special Prosecutions Rural Prosecution Unit.

Gregory’s case didn’t go to trial, but his sentencing was a result of a partial plea agreement allowing Judge Peters to sentence Gregory to serve between 20 and 45 years for his plea of guilty to one count of murder in the second degree. Although this was a sentencing, witnesses did testify in this case.

“And homicide cases are always difficult because a person is lost; there is a person who's gone. And in this case, it was Cheryl Sakar, someone who was a mother to her now 16-year-old daughter and a sibling, sister to her three siblings, and a friend to so many people in Crooked Creek, and a co-worker, and someone that people really loved. And there's always a lot of emotion that goes on with that, of course, because she was someone who really mattered and who's now gone from that community,” Woolfstead said.

According to the National Institute of Justice, almost 85% of American Indian and Alaska Native women have experienced violence in their lifetime. That’s more than four out of every five Alaska Native women. Gregory admitted to beating his girlfriend Sakar many times before.

“And despite her familiy's pleas for her to report any of these prior domestic violence incidents to the police, Miss Sakar didn't. And she didn't, as she told her family, because she loved him. And they lived together and they were dependent on each other,” Woolfstead said.

Sakar would call her brother, Michael Pepperling, sometimes when she was being abused by Gregory to come pick her up. Sakar even called Pepperling on the night she died.

“And the court heard in the sentencing a voicemail that was left on her brother, Mr. Pepperling's, phone of her begging for Mr. Gregory to stop, to stop hurting her. And Mr. Gregory can be heard continuing to assault her,” Woolfstead said.

At sentencing, Gregory did apologize to the Sakar family and he apologized to the court.

“He never denied his involvement in the case. From day one, when troopers arrived, what he said was that he was intoxicated to the point of blackout. That he could not remember what had occurred the night before. But that if anything happened to her, it was probably him because he blacked out and assaulted her in the past,” Woolfstead said.

In handing down the sentence, Judge Peters recognized the completely senseless and avoidable nature of the crime. He recognized that Gregory took responsibility for his actions and apologized to Sakar’s family. Peters recognized that Gregory was controlling and manipulative of Sakar, and that Sakar was a vulnerable victim who had been repeatedly assaulted by Gregory. The judge found that an aggravated sentence was appropriate. The prosecutor hopes that this delivers a message.

“If there is anything that can come out of this, I would encourage others who are in similar situations to Miss Sakar to report when things occur to them. Because, as Miss Sakar’s sister, Miss Ausdahl, said at the sentencing, that's not love, that's domestic violence. And to reach out to organizations like Tundra Women’s Coalition here in Bethel that can come up with things like a safety plan,” Woolfstead said.

Woolfstead also said that there are things that advocates can do to help people in these situations if shelters aren’t an option or available, whether it’s creating future safety plans or calling a hotline.

The National Domestic Violence Hotline is available 24/7; the number is 800-799-7233. The Bethel Tundra Women’s Coalition Crisis Line is 1-800-478-7799

Editor's note: In a previous version Cheryl Sakar was referenced as Gregory's wife when in fact they were not married.

Francisco Martínezcuello is the KYUK News Reporting Fellow and a graduate of UC Berkeley School of Journalism. He is also a veteran of the United States Marine Corps.