An Orcas Island man with a long list of criminal convictions faces no less than a year in prison following a late November altercation with deputies and assault of his live-in girlfriend.

On Dec. 9, Brian Kelly Nelson Bernstine, 30, pleaded guilty in San Juan County Superior Court to one count of third-degree assault, a Class C felony, and to one count of fourth-degree assault, a gross misdemeanor. Bernstine, identified as a Woodinville resident in court records, is slated to be sentenced Jan. 13 under a drug offender “prison-based” sentencing alternative. He was ordered to held in custody pending that mid-January sentencing hearing.

Bernstine, convicted of six misdemeanors this year alone, including fourth-degree assault and violation of a domestic violence protection order, was arrested Nov. 29 on suspicion of assault and taken into custody at his Green Cow Lane home in late afternoon.

He did not surrender willingly, however.

According to court documents, Bernstine struggled with deputies inside the home and became increasingly combative after two of three officers involved in the arrest steered him into a patrol car. He reportedly began kicking a window of the patrol car and then began kicking both deputies as they tried to get him to stop. He was struck at point-blank range by a Taser at least seven times and became, according to court documents, even more aggressive before deputies were able to gain control and secure him inside the squad car, and then close its doors.

A Class C felony, third-degree assault carries maximum penalties of five years in prison, a $10,000 fine, or both. The standard range of sentencing set by the state, given Bernstine’s criminal history, is 17-22 months. He will be required by court order to pay the medical costs of his 22-year-old girlfriend, who he reportedly hit in the face the morning before the arrest and who suffered two black eyes.

According to court documents, Bernstine had already been convicted of six felonies and 22 misdemeanors since 1998, prior to pleading guilty to the recent offenses. Though the majority of prior convictions consist of property crimes and driving offenses, the list also includes three misdemeanor assaults and one felony assault, as well as several drug-related crimes.

Under the prison-based sentencing alternative, Bernstine will first be evaluated by state Corrections officials as to whether he would qualify for an in-prison drug treatment program. If that alternative is accepted by the judge, his sentence would consist of confinement in a state-run facility for at least 12 months.