District of Columbia Superior Court Judge Gregory Jackson’s courtroom buzzed when a man in an orange prison jumpsuit revealed he was a former judicial officer and veteran attorney.

George Crawford, who served as chief administrative law judge for the city’s Department of Employment Services until late last year, has been in jail since April 15 after he was found in contempt for failing to comply with court orders in a civil lawsuit over unpaid loans.

On April 30, Jackson ordered Crawford to stay locked up without bond until he pays more than $123,000 in sanctions. It was Crawford’s second stint behind bars in the case. In December, he was jailed for more than a week after Jackson found Crawford "demonstrated a loathsome pattern of noncompliance."

"I have racked my brain to try to understand what it is that compels you to not resolve this," Jackson said to Crawford during the latest hearing.

Crawford’s lawyer, Leonard Long Jr., a Wash­ington solo practitioner, declined to comment following the hearing, as did lead counsel for the plaintiffs, Stephen Neal Jr. of Alexandria, Va.’s DiMuroGinsberg. During the hearing, Long said he had discussed possible options with Crawford for making payments. Neal told the judge he hadn’t heard anything, calling the situation "outrageous."

Crawford, a member of the D.C. Bar since 1980 with no history of disciplinary action, has a long record of public service. From the late 1980s through 2001, he served as general counsel of the D.C. Taxicab Commission and, for a time, as interim commission chairman. As chief administrative law judge at the employment services department beginning in September 2011, he oversaw proceedings for claims brought under workers’ compensation benefit programs.

The D.C. employment services department confirmed that Crawford was fired on December 31, but declined to disclose the reason. Crawford was released from his first stint in jail 10 days before his termination.

The underlying civil case began in 2007, when Crawford was one of several defendants sued by First Washington Insurance Co. for breaching loan promissory notes. Crawford, according to the complaint, agreed to guarantee the notes. First Washington claimed Crawford and the other defendants were "seriously delinquent" in making loan payments and sued for the money owed.

In December 2009, a judge previously assigned to the case entered a judgment against Crawford for $1.15 million. The judge then ordered the parties to mediation, and First Washington and Crawford reached a settlement. Crawford agreed to pay $10,000 over three years and provide an affidavit listing his assets and liabilities.

Over the next few years, First Wash­ington, represented by Neal of DiMuro­Ginsberg, accused Crawford of willfully disobeying orders to pay the settlement and to turn over his financial information. Crawford’s noncompliance with the settlement terms meant he faced the original million-dollar judgment. He was found in contempt and Jackson sent him to jail for the first time on December 10 after he failed to pay more than $30,000 in sanctions.

Crawford was released on December 21 after making payments on the first round of sanctions; he eventually paid the full amount. By that time, however, he owed an additional $123,000 in sanctions and was sent back to jail on April 15 after Jackson found he had failed to make "good-faith" efforts to pay.

During the April 30 hearing, Crawford insisted he couldn’t pay what he owed. Jackson rejected the claim, noting that Crawford had earned a comfortable government salary, owned a home and a rental property, and had four cars.

Crawford had worked hard to get those assets, the judge said, "but you’ve made some bad decisions."

Contact Zoe Tillman at ztillman@alm.com.