New at-large D.C. Council hopeful Jimmy Calomiris says he’s not a career politician. He’s not even confident about how long a Council term lasts.

“I’m pretty sure it’s a four-year term,” Calomiris says, correctly.

Calomiris might be shaky on some of the details, but the lawyer and real estate businessman says he’s ready to fix the District’s government. Before he can get to the Wilson Building dais, though, Calomiris will have to defeat incumbent David Grosso and convince general election voters to look beyond his previous domestic violence charge and positive tests for cocaine.

Calomiris, a 51-year-old Dupont Circle resident, left the Democratic Party earlier this year to set up his bid for the citywide at-large seat reserved for non-Democrats. He doesn’t shrink from criticizing Grosso, the chairman of the Council’s education committee, who Calomiris claims reacted too slowly to revelations about lead in the water at District schools.

“If this is the tip of the iceberg, what else is in there?” Calomiris says of the conditions at schools.

Calomiris, who comes from a prominent District real estate family, fits a classic outsider business candidate mold. He wants to institute term limits on councilmembers, spiff up public schools, and launch an easier permitting process at the Department of Consumer and Regulatory Affairs. If he has so much trouble at DCRA, Calomiris wonders, how much trouble do less well-connected people have?

Complaining about DCRA is typical for Council candidates. Here’s what is unusual: Calomiris’ disturbing criminal record.

In March 2006, Calomiris was charged with simple assault after police responded to a call in Friendship Heights. According to the police report, Calomiris’ then-girlfriend told police that she was asleep in the master bedroom when an intoxicated Calomiris tried to wake her up. Attempting to avoid him, she went to the house’s guest bedroom, but Calomiris allegedly grabbed her and threw her into a wall, according to her.

Calomiris’ attack bruised his girlfriend’s shoulder, according to the report. Then, Calomiris’ girlfriend told police, he hit her girlfriend in the face, giving her a nosebleed.

Calomiris soon pleaded guilty. But nine months later, prosecutors were back in court asking a judge to revoke Calomiris’ original agreement, alleging that he had tested positive twice for cocaine while under court supervision.

“[Calomiris] shows no commitment towards changing his lifestyle,” one supervision officer noted in a report.

Calomiris was ultimately sentenced to six months of probation, along with a suspended jail term of 180 days. Calomiris’ then-lawyer blamed his client’s substance abuse on the emotional effects of once being robbed at gunpoint.

“I made a mistake,” Calomiris says of the assault on his girlfriend. “I’m not hiding from it.”

An earlier domestic violence charge from 2005 was eventually dropped by prosecutors. That case file was not immediately available for review at D.C. Superior Court.

Calomiris’ legal troubles popped up again in 2013, when police arrested him for driving on Connecticut Avenue NW with a revoked driver’s license. Calomiris pleaded guilty and was sentenced to six months of probation.

With November’s general election five months away, Calomiris has started building his campaign infrastructure. He’s hired campaign operatives John Rodriguez, who worked on failed at-large hopeful David Garber‘s campaign, and Josh Brown, a former staffer for At-Large Councilmember Anita Bonds who ran Ward 2 Councilmember Jack Evans‘ unsuccessful 2014 mayoral bid.

As Calomiris described his campaign message to LL (“Government is broken”), Brown cut in.

“You’re going to shake things up,” Brown predicted.

Update 6 p.m.: The campaign sent LL the following statement:

“Jimmy is running for the Independent seat on the DC Council because District voters understand that our local government can and should work better. Jimmy knew that running for Council in the City that raised him would undoubtedly mean that there would be a light shed on his successes in the District, and his mistakes. Jimmy has nothing to hide, and he has not shied away from his past, but here are the facts:

In 2005, charges were brought against both Jimmy and his then-girlfriend, and these charges were subsequently closed without any finding on either party. In 2006, an assault charge was brought against Jimmy, and he subsequently pleaded guilty after deciding with his counsel that the best course of action was to move forward and better himself.

While it is correct that two of the over ninety drug tests came back positive for cocaine, both the April 5, 2007 sentencing memorandum and the drug test report indicate that Jimmy subsequently enrolled in a 28-day inpatient substance abuse treatment program at Warwick Manor Behavioral Health, and tests thereafter came back negative. As a result of completing conditions of probation to the court’s satisfaction, and the fact that Jimmy’s then-girlfriend moved to vacate any conditions of a protective order within two weeks of the case’s inception, the Court and United States Attorney’s Office saw it fit to grant Jimmy’s request for unsupervised probation.”