BRATTLEBORO -- A local man was ordered held without bail after allegedly violating an abuse prevention order by talking to a woman authorities say he had stalked and threatened to kill.

According to court documents, Timothy O'Keefe, 46, was cited on June 30 for two counts of violating an abuse prevention order and one count of obstructing justice. Windham County State's Attorney Tracy Shriver said the first two counts have been heightened to felonies due to habitual offender status as a result of O'Keefe's criminal history, while obstructing justice is always a felony. O'Keefe faces up to life in prison for each offense.

George Friend, a deputy with the Windham County Sheriff's Department, filed an affidavit that states he was on duty at Windham Superior Court: Criminal Division on the morning of June 30, when he saw O'Keefe "standing at the driver side door of a black truck and talking to a female subject who was still seated in the vehicle with the door partly opened." Friend states he recognized O'Keefe from the man's previous dealings with the court.

Friend said he headed in their direction and O'Keefe walked right past him and into the courthouse. Friend identified the woman O'Keefe was talking to and learned she had a order of protection, out of New Hampshire, against O'Keefe. The woman produced a copy of the order, which states O'Keefe is not allowed to have contact with her or come within 300 feet of her. O'Keefe was then arrested in the first-floor hallway of the courthouse.

The woman completed a sworn written statement in which she said O'Keefe approached her at her car and asked her to "fix things" so she could see one of his young relatives. Friend states the woman was visibly shaken by her interaction with O'Keefe.

According to court documents, O'Keefe had previously been convicted of domestic assault, driving under the influence of alcohol for a third time, aggravated stalking, and two charges of violating an abuse prevention order.

An affidavit filed by Probation and Parole Officer Phil Damone states O'Keefe was sentenced in April 2012 to two years in prison for aggravated stalking as a result of his threatening contact with the same woman he was talking to outside the courthouse on June 30. Damone reports O'Keefe engaged in alleged criminal threatening against the woman and a young relative while behind bars, and he was released in April.

According to an affidavit filed by Brattleboro Sgt. Mark Carignan, O'Keefe was incarcerated at the Lee Adjustment Center in Beattyville, Ky., and made phone calls to another young relative asking him to find out where the victim of his alleged stalking resides. O'Keefe then asked the young relative to get a gun and hold it for him until he gets out of jail. The young relative declined the request, telling O'Keefe the weapon would be traced back to him. O'Keefe, nevertheless, then gave the young relative instructions on how to purchase a gun privately -- not at a gun store -- and not register it.

O'Keefe, according to Carignan, also said he wanted to give someone cash to assault the victim. He then asked the young relative to "talk some sense" into her. Carignan states in the affidavit that he spoke with the young relative, who said he did not do anything O'Keefe asked him to because he knew it was all against the law.

According to Carignan, O'Keefe also contacted a relative who worked with the Vernon Police Department. O'Keefe allegedly asked the relative to use a computer to look up information on the victim and her boyfriend. The relative said she would not do that. O'Keefe also said he wanted the relative to assault the victim.

"I'll pay you to take a ... day off and go over there and beat her up, take her ... phone and unblock (my phone number)," he is quoted as saying.

A separate affidavit, filed by Brattleboro Police Officer Adam Belville, states O'Keefe in 2013 also made calls to the young relative he and the victim were talking about on June 30 and threatened to kill the victim of his alleged stalking and anyone else he had to. He also told the victim she would have "an issue" once he got out of prison.

Belville also reports that O'Keefe, while at the Southern State Correctional Facility in Springfield, had attempted to send letters to Probation and Parole Officer Henry Farnum, who was a witness in criminal cases that were active at the time. The first letter was laced with profanity and threatened to "trim (Farnum's) family tree until it looks like a telephone pole." Belville states the letter was intended to look as if it was written by someone other than O'Keefe, but the penmanship in both letters in identical. The second letter, according to Belville, was much more formal and offered an apology. It stated, "I'm sorry for what I said about your Family, IF any thing [sic] happens to them, it will not be my doing, as I will be in Springfield sitting in prison."

Belville reports that Correctional Officer Andrew Thibault listened in on a phone conversation O'Keefe had with a young man and O'Keefe admitted to penning both letters.

According to Belville's affidavit, O'Keefe also allegedly assaulted the female victim by "punching her in the head through a screen door at his residence" and caused physical pain. O'Keefe was convicted of domestic assault and was sentenced to 12 to 16 months behind bars for that offense.

Domenic Poli can be reached at dpoli@reformer.com, or 802-254-2311, ext. 277. You can follow him on Twitter @dpoli_reformer.