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Harold Gregory Sentenced to 33 Years for Murder of Girlfriend

May 23, 2023

(Bethel, AK) –Today, 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 for the 2019 beating death of his girlfriend, Cheryl Sakar. This sentencing was a result of a partial plea agreement allowing Judge Peters to sentence Gregory to between 20 and 45 years to serve for his plea of guilty of one count of murder in the second degree.

Gregory admitted, and Judge Peters found, that an aggravating factor applied to his case given that it was a crime of domestic violence. Sakar’s family spoke to the court at sentencing and the court heard testimony from four witnesses. Harlan Waskey testified about finding Sakar injured in the home she and Gregory shared and his efforts to assist her. He described that Gregory continued to drink with his friends as Waskey tried to help Sakar. Medical Examiner Norman Thompson testified about the external and internal injuries to Sakar that he observed during the autopsy. Alaska State Trooper Sergeant Elondre Johnson testified about the investigation into the case and the crime scene. He also described Gregory’s admissions that he had previously gotten drunk and assaulted Sakar and said that if she was hurt, he was likely the cause of her injuries. The court also heard an audio recording of a message Sakar left on her brother’s phone, seeking help as Gregory assaulted her.

Sakar’s family spoke to the court at sentencing. Michael Pepperling, Sakar’s brother, testified about the prior domestic violence he knew Gregory committed against Sakar, and the family’s efforts to convince Sakar to report those assaults to law enforcement. Her sister, Roxanne Ausdahl, told the court about Sakar’s life, her daughter, what a good sister and mother she was, and how they tried to get Sakar out of the domestic violence relationship with Gregory. Ausdahl stated “That is not love. That is not how you treat someone you love. That is not love, that is domestic violence.” Pepperling spoke directly to Gregory, stating “No matter how much time you get you are lucky. You get to have a life. You taking her life away, she doesn’t get to have a family. She doesn’t get to see [her daughter] grow up.”

Prosecutor Bailey Woolfstead asked the court to impose a 45-year sentence, focusing on the defendant’s numerous prior unreported assaults of Sakar under similar circumstances, the severity and number of her injuries, and Gregory’s failure to seek assistance while. Sakar died over a period of time. The defense asked for the minimum 20-year sentence.

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. Judge Peters recognized that Gregory was controlling and manipulative of Sakar and that Sakar was a vulnerable victim who had been repeatedly assaulted by Gregory and found an aggravated sentence was appropriate.

The case was prosecuted by Former Bethel District Attorney R. Christopher Knowles and Assistant Attorney General Bailey Woolfstead of the Office of Special Prosecutions Rural Prosecution Unit.

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Department Media Contacts: Communications Director Patty Sullivan at or (907) 269-6368. Information Officer Sam Curtis at or (907) 269-6379.