DC man says it took six years to evict ex who never paid rent

DC man tried for 5 years to evict tenant

A Washington, D.C. man has spent years trying to evict his ex-girlfriend from a house he owned, without her paying a penny. Now, DC may soon vote to change landlord-tenant laws.

WASHINGTON - As the DC Council debates changes to landlord-tenant laws, one homeowner says his case shows how difficult the process can be.

It can be challenging to evict someone in Washington, D.C. That’s by design, the result of policy choices made over years. Now, as the D.C. Council considers the Rental Act, which could alter some of the city’s landlord-tenant dynamics, one man’s story underscores how complicated the system can be.

Doug Cleary says it took him six years to remove someone from his property — a woman he once dated who, he says, never paid rent.

"Yeah, it’s been a nightmare. This is six years of my life," said Cleary.

Steven Krieger, an attorney who represented him, called it "definitely the worst eviction case" he’s ever handled. "I mean, six years to evict somebody is just crazy."

Dig deeper:

Cleary says the ordeal began after the relationship ended in 2019. He and his ex-girlfriend had been together for three years and planned to share a home he owned.

"And we just had, you know, a normal girlfriend, boyfriend-girlfriend relationship until…," Cleary said. "The trouble started in September 2019."

After their breakup, Cleary’s ex claimed they were married under common law, which tied up the property for years before a D.C. judge determined that was not true.

"And she stayed there from 2019, when the eviction started, you know, through almost the end of 2025," Krieger said. "She has not paid a penny towards anything."

Even after Cleary won the common law marriage fight, he says the eviction dragged on for years. His ex filed multiple appeals, twice winning emergency stays from the D.C. Court of Appeals, despite disobeying court orders to pay a bond or place money in escrow.

"Yeah, I mean, it was… it was a series of, I think, very bizarre rulings from… from the courts, sort of across the board," Krieger said.

What they're saying:

Krieger, an experienced housing lawyer, argues that D.C. has made it too difficult for landlords to evict tenants.

"There’s also so many just basic technical requirements that could be a problem for a landlord, even if the occupant is not difficult," he said. "Like, if you don’t have GPS coordinates on the pictures showing that you posted the notice, the case gets dismissed."

Cleary says his ex never paid rent, which should have been $4,000 a month over more than five years. 

"I don’t even want to try to calculate how much money I’ve spent," he said. "My guess is at least 100,000, and probably more."

Even after she was finally evicted this month, Cleary says the ordeal isn’t over. He’s still pursuing a civil lawsuit to recover some of his losses.

"So, you know, relief at first, but still, the nightmare for me is continuing," Cleary said.

FOX 5 has reached out to the woman involved and will update this story once we receive her statement.