But Thursday dressed in prison clothes and handcuffs, Willhoit faced Circuit Judge Robert Gillum without having paid the promised money. Both the judge and Assistant Commonwealth's Attorney Daryl Day expressed their frustration with the development.
"He doesn't have the $10,000," said Berryman. "It leaves us in a quandary."
"It doesn't leave me in a quandary," Gillum said. "I guess he's going to serve some time then. He's obviously not going to meet the conditions of probation... He lied to the court."
Willhoit, of Lexington, was originally arrested in June and was charged with conning potential investors, including Stanford Mayor Eddie Cater, into opening accounts with his false investment company, Net City, a supposed subsidiary of National City Bank.
Willhoit was later indicted on three counts of fraudulent acts pertaining to securities, three counts of failure to register as a broker/dealer, three counts of failure to register securities and three counts of theft by deception more than $300.
As the hearing proceeded, Day clearly became agitated at Willhoit's inability to pay back the victims, especially if he was sent to prison, and asked Gillum for a delay in the case for "time to think about it."
Outside the courthouse, Willhoit's mother smoked a cigarette nervously and discussed the case with Berryman. Willhoit's family had unsuccessfully tried to raise the bail money before court.
"There's no way you can come up with the $10,000?" asked Berryman.
"No, not yet," she replied. She did not return to the courtroom.
Willhoit's final sentencing
Almost an hour later, Willhoit and Berryman appeared again before the judge for final sentencing.
"Since you cannot pay at this time, is it your understanding that the plea agreement no longer exists," asked Gillum, to which Berryman agreed.
Day said he believed any offer of parole at that point would "seriously and unduly depreciate the seriousness of the offense for which he's pleading guilty," especially in light of his broken promise to repay duped investors.
Day recommended a sentence of 10 years, with the possibility of shock probation on the condition that Willhoit remains on probation until full restitution has been made. "No matter how long it takes him," Day added.
Prior to the delay, Willhoit quietly addressed the court with remorse and asked to be allowed to repay his debt while on probation.
"Over the last six months I've realized how much harm and trouble I've caused," he told Gillum. He asked to be able to "use probation time as a blessing to turn my life around."
"I promise you that I'll work so very hard to repay this debt and live a life of integrity," Willhoit said.
The judge did not buy Willhoit's speech.
"I think you are a con artist. I think that you are trying to con us today," Gillum said as he sentenced Willhoit to 10 years in prison with credit given for 183 days served.
At one point, Willhoit's attorney whispered to Carter, "I'm sorry, I've done everything I could."
Gillum also had stern words for Hill, who was convicted in 2003 of stealing $280,000 from the industrial board, where she was employed.
Hill not meeting probation requirements
Hill was granted shock probation after serving less than 6 months of her 10 year sentence. At that time, she was ordered to pay $200 a month in restitution, later raised to $500, and provide 20 hours of community service per week. But Hill had not provided the Commonwealth Attorney's office with documentation of her community service, which landed her in court Friday.
Hill said she had filed the proof of her community service with the parole office, but it was lost during staff changes. She said she wasn't aware it had to also be filed with the Commonwealth Attorney. Gillum ordered that she do so.
Hill had also seen outside the county, which Day said violates the conditions of her parole.
"When I signed the original paper work, it was not a stipulation" that permission was needed to leave the county, Hill said.
But Gillum pointed at the document and said, "It says right here on this order, 'Remain in Lincoln County.'"
"I didn't know that, your honor," replied Hill. She then claimed the stipulation was unrealistic because she worked in Boyle County and, as a cheerleading coach, traveled frequently with the squad. It was not immediately clear where the convicted felon was a coach.
Before a terse dismissal, Gillum ordered Hill not to leave the county in the future without express permission from the parole office.
"Stay in Lincoln County except to work, one hour after and one hour before in Boyle County," the judge said.