A series of escalating disputes between a Roanoke landlord and an attorney with the Legal Aid Society culminated this week in general district court with the businessman being ordered to pay $35,000 in damages and fees.

Robert Harris, who owns rental properties in Roanoke, also was hit with restrictions including a two-year protective order that bars him from contact with Legal Aid attorney Emily Jewett — to whom Harris sent dozens and dozens of inflammatory emails — as well as a ruling that prevents Harris from filing suits against other lawyers or law firms without counsel.

Harris, representing himself, initially had sued both the Legal Aid Society and Jewett, who represents a former tenant of Harris’. He claimed that Jewett lied in court during a recent hearing regarding the tenant’s overdue rent, and he further accused Jewett of damaging a furnace during a visit to one of his properties.

But Jewett and Legal Aid brought a counter claim against Harris, arguing that his accusations were unfounded and abusive, “interposed to harass and to intimidate the defendants, and to dissuade them from representing tenants who reside in Harris’s rental properties in the future.”

Among other communications, their attorney, Jason Whiting, submitted an email he received from Harris, an offer to settle his suits with one proposed condition being that “legal aid would have to agree to never ever in my life time d- — with me and waste my time in court OR COME against me ever again.”

At a hearing Wednesday, the court concurred with Whiting’s arguments.

“I’ve been out of law school 45 years and I don’t think I’ve ever seen a worse case of abuse of process,” Judge Woody Lookabill said, and dismissed both of Harris’ claims as insufficient. He ordered Harris to pay $25,000 in sanctions — $5,000 more than was requested — as well as $10,000 in legal expenses.

The protective order imposed by Lookabill arose over communications Jewett said she started receiving from Harris in December, when she took on one of his tenants as a client.

“That day began the harassment,” Jewett said in court. “He started sending me emails, calling me a lying b----.”

A complaint Jewett filed in criminal court this month said that since then, she has received more than 180 emails from Harris, and at Wednesday’s hearings, Whiting presented notebooks filled with copies of the communications.

Some of the emails, ostensibly related to the tenant issue, referred to Jewett as “pretty,” “cute” and “attractive,” while later ones dropped references to personal details, information he found online — her children, her address, amounts owed on personal mortgages and remarks about her neighborhood. Others were far more graphic and included explicit aggressive statements.

“The bulk of the language used in numerous emails is overtly sexual and implicitly violent,” she wrote in her criminal complaint.

Attorney Steve Baker represented Harris on the matter of the protective order. During his cross-examination of Jewett, she acknowledged that Harris had never called or texted her, and that he hadn’t contacted her family or spoken to her in person anywhere other than the courthouse.

She also said that during a run-in with him earlier this month, she called him a “motherf-----” in public.

“Was that unprofessional? Yes, it was,” she told the court.

But she balked at Baker’s suggestion she could’ve simply passed the tenant’s case on to another colleague.

“There is absolutely no world in which an attorney should not be allowed to do her job,” Jewett said.

Harris testified as well and, in addressing his emails, presented himself as a landlord who often represents himself in local courts, laying claims to success on that front but also arguing that he was the underdog.

“Legal Aid forces other parties to hire lawyers,” Harris told the judge. He said he was simply trying to recover money lost.

“I’m pro se. The deck’s stacked against me,” he said, and claimed that his messages to Jewett had been merely part of his litigation strategy, a tactic to “get under their skin” and put opposing counsel off their game.

“I meant Ms. Jewett no harm,” he said, and added he had no wish to have further contact with her.

Future encounters seem inevitable, however.

Jewett’s criminal complaint against Harris, a charge of misdemeanor harassment by computer, is set to be heard in August, while Harris and his former tenant have counter-claims against each other in civil court, with Jewett still representing the tenant. Those also have hearings set for next month.

Harris said in court he intends to appeal the judge’s decisions but, reached by phone Thursday, he declined to comment further. Baker also did not respond to messages.

Asked about the cases Thursday, Whiting in an email called them “a distraction” for the Legal Aid Society from its work.

“I am hopeful that Judge Lookabill’s severe and decisive verdict in favor of legal aid will discourage similar misconduct and abuse of the judicial system we rely upon to solve real issues in our society,” Whiting wrote.

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