Former Roanoke City councilman Robert Jeffrey Jr.’s temporary leave from jail on bond last week marked an unusual twist in his ongoing legal saga.

Prosecutors argued Jeffrey poses a danger to the community’s “financial security” ever since he was found guilty in March of defrauding the city and embezzling from a local nonprofit.

“All of this is a pattern of behavior,” Assistant Commonwealth’s Attorney Sheri Mason said in court during a bond hearing last Wednesday. “He quite honestly just steals money from people.”

Mason said Jeffrey should stay in jail until his Aug. 22 sentencing. But if a bond was required, it should be set at $200,000 cash, she argued — the amount prosecutors say he stole from the nonprofit Northwest Neighborhood Environmental Organization.

Roanoke Circuit Court Judge David Carson — responding to a higher court’s decision after an appeal from Jeffrey’s defense attorney — agreed to set bond. He ordered bail to be set at a $25,000 bond or $2,500 in cash.

“It obviously would be this court's preference that a cash bond be posted so at least there's a start on compensing the victims in this case,” Carson said.

Instead, Jeffrey posted a $25,000 bond through Valley Bail Bonds.

The former councilman’s financial situation raises new questions about how, exactly, Jeffrey plans to make amends, returning the hundreds of thousands of dollars he was found guilty of embezzling. And his actions within an hour of being released from jail — taking a quick trip to the grocery store — likewise raise questions about how legitimately he views his punishment.

City records show Jeffrey cited more than $100,000 in personal debts as recently as January. He has unpaid city fees related to RLJ Property Management, his company at the heart of the embezzlement case, according to Roanoke's treasurer. And in May, a billing agency filed a civil lawsuit against Jeffrey in Roanoke City General District Court claiming he owed thousands in unpaid medical bills and related expenses.

Asked if prosecutors were aware of the latest lawsuit, Commonwealth’s Attorney Don Caldwell said in an email, “The pending civil suit would not be something that the Court would consider in a criminal bond hearing.”

Yet prosecutors did argue in the bond hearing that Jeffrey’s past struggles with money — including civil actions and a 2010 bankruptcy — demonstrated why he should be denied bond.

That history shows that Jeffrey “makes bad business dealings, he takes out loans with no intent to pay them back,” Mason argued. “He has demonstrated that if he gets close to somebody and gains their trust, that he will take money from them.”

Carson had sided earlier with the prosecution.

In a June bond hearing, Carson said Jeffrey’s conviction of three felonies and the potential sentence of 22 to 57 months in prison called for him to remain in jail.

But on July 19, a three-judge panel of Virginia’s Court of Appeals found that Carson’s court had “abused its discretion” when it denied Jeffrey bond.

Melvin Hill, Jeffrey’s defense attorney, argued the appeals court ruling mandated Jeffrey be granted bail. Hill said Jeffrey’s age, lack of previous criminal convictions and health — he is undergoing treatment for kidney failure — warranted release from jail.

He rejected prosecutors’ characterization that Jeffrey posed a financial threat to the community.

“It’s not that Mr. Jeffrey will be out and about,” Hill said, “engaged in business transactions, engaged in business, when he’s released.”

In setting bond, Carson said Jeffrey was to “be essentially under house arrest.”

“That means that he is at his residence,” Carson said, “and the only time he is not at his residence, if he makes bond, is … one, if he is visiting with his attorney; two, if he is otherwise required in court; or three, if he is receiving medical care. So under one of those three instances you can be outside of his residence. Otherwise, he is at his residence 24/7.”

Jeffrey was considered released at 4:03 p.m., according to the city jail. He was seen walking out of the jail at 4:25 p.m., according to a Roanoke Times photographer on scene.

A short time later, Jeffrey and his mother, Evangeline, walked into the Towers Shopping Center Kroger. He wore a charcoal black suit and a smile.

In a snack food aisle near the entrance, they ran into this reporter at about 5:10 p.m. and exchanged awkward pleasantries.

Two minutes later, he and his mother were seen at the checkout stand. The Towers Kroger lies between the city jail and Jeffrey’s residence in Raleigh Court.

Jeffrey and Hill did not respond to messages seeking comment.

Caldwell said restitution to the Northwest Neighborhood Environmental Organization would be addressed at Jeffrey’s sentencing hearing. He did not know what plans, if any, Jeffrey had to compensate his victims. The leader of the nonprofit declined to comment.

Jeffrey’s ready ability to pay back the money appears tenuous, however, according to public records.

Each January, members of Roanoke’s city council must file a “statement of economic interest” with the city that explains their approximate income and whether they owe money.

In Jeffrey’s 2021 statement, he did not list any personal debts.

(It’s not clear whether that reflected reality. In his March conviction on obtaining money by false pretense from Roanoke’s Economic Development Authority, a jury found Jeffrey had falsified financial information on a government form.)

However, in Jeffrey’s 2022 economic statement, he cited more than $100,000 in debts.

In a section of the report for “My personal debts,” Jeffrey indicated owing more than $50,000 to insurance companies and more than $50,000 to stock, commodity or other brokerage companies. He also marked a box indicating credit card debt of between $5,001 and $50,000.

In another section of the report listing “The personal debts of members of my immediate family,” he listed the name as “Robert Jeffrey” and indicated credit card debt to Credit One Bank as between $5,001 and $50,000. It’s not clear whether Jeffrey was referring to himself; his father, who lives in Seattle, shares his first name.

Details about the debt remain murky. While Jeffrey answered “no” to a question about whether he or family owed more than $5,000 to “any one creditor,” he filled out the subsequent sections. Instructions said those sections only needed completion with a “yes” answer.

Court records also illustrate Jeffrey’s current financial situation.

A medical billing agency took Jeffrey to court on May 24, at which time he was still in jail.

Medkey Inc. claims Jeffrey owes the company $1,567.83 in medical expenses, and with interest and other fees is asking that he give up $2,650.95, according to court documents. Jeffrey has numerous health issues, which was a key factor in his temporary release from jail.

A hearing in that case was scheduled July 20 and then pushed back — after no attorney for Jeffrey showed up at court — to Aug. 17, five days before his sentencing.