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LL recently checked through court records to see if any of the candidates for the special at-large D.C. Council race had any legal problems involving stealing large amounts of public funds or lying on a bank loan application in order to buy a boat. Everyone passed!

But LL did find a bankruptcy filing by John Settles, a political noob who had a campaign event today at Ben’s Chili Bowl that’s being hosted by some associates of former Mayor Adrian Fenty. Settles filed for bankruptcy in 2011, with court records listing $3.4 million in unpaid liabilities, including several years of federal tax liens.

Since personal financial problems, to one degree or another, played a role in the resignation and guilty pleas of former Ward 5 Councilmember Harry Thomas Jr. and former D.C. Council Chairman Kwame “Fully Loaded” Brown, as well as in the recent defeat of former At-Large Councilmember Michael Brown (who’s running again), any candidate with recent financial problems might have a serious liability.

But Settles says his situation is far different from the above-named pols and he doesn’t see it being a major issue on the campaign trail. Settles says his bankruptcy is the result of some real estate investments in Georgia gone sour during the housing collapse, not because of any mismangement of his personal finances.

“I was an entrepreneur,” says Settles, who is currently a mortgage banker. “This isn’t an ethical thing, this is an entrepreneurial thing.”

Settles says the tax liens resulted after he was audited by the IRS and there were some issues involving capital gains tax exemptions. He says he filed amended returns and has since paid what he owed.

A native Washingtonian who says he felt compelled to run for the Council because he was frustrated with the city’s current elected leaders’ “lack of focus” on key issues, Settles also notes that filing for bankruptcy is not uncommon for real estate investors.

Settles adds that he’s been up front about his bankruptcy with potential supporters and is more than happy to explain what happened to potential voters.

“Entrepreneurship is tough,” he says.