Clinton Killian, a candidate for Oakland City Council, is the new darling of the local business community. Last month, the fifty-year-old ex-city planning commissioner and former member of the AC Transit board of directors won the coveted endorsement of OakPAC, the political arm of the Oakland Metropolitan Chamber of Commerce. The endorsement immediately stamped Killian as one of frontrunners in the race for the city's at-large council seat. But it turns out the PAC had no idea that a slew of legal and financial troubles have plagued Killian over the years.

Killian's problems, in fact, were so severe that they raise questions as to whether the Oakland lawyer possesses the financial acumen to serve on the council at a time when the city is facing multimillion dollar deficits this year and next. Public records show that over the past decade, Killian went bankrupt in a case in which claims of more than $825,000 were made against him. Plus, the city of Oakland, the state, and the federal government all placed numerous liens against him and his property for failure to pay more than $133,000 in taxes and fees. He also was sued by a state agency representing his former law clerk, who claimed he sexually harassed her. His former landlord sued him for allegedly failing to pay his rent. And his own lawyer sued him for not paying his legal bills. In addition, he lost his seat on the AC Transit board in 2000 when he failed to gather enough signatures to qualify for the ballot.

Public records show that none of Killian's opponents — or any sitting councilmember — has experienced so many legal and financial difficulties. Indeed, no one even comes close. Killian's opponents for the at-large seat are Oakland school board member Kerry Hamill, AC Transit board member Rebecca Kaplan, public safety activist Charles Pine, and management consultant Frank Rose.

Scott Peterson, public policy director for the chamber of commerce and facilitator of OakPAC's endorsement interviews, said he believes the political action committee's board did not know about Killian's legal and financial history when it chose to back him. "I wasn't made aware of it," Peterson said. "It certainly didn't come up in the endorsement interview."

OakPAC is one of the most highly sought after endorsements in local politics because the group has a history of spending lots of money to help elect its favored politicians. Peterson said that OakPAC required all of the candidates to fill out a questionnaire, but he said it did not ask questions about "their personal financial dealings." When asked whether the OakPAC board would have changed its mind about Killian had it known about his checkered legal and financial history, Peterson replied: "I don't know. That would be up to the board."

OakPAC board chairman Michael Colbruno, an executive for Clear Channel Outdoor billboard advertising and vice chairman of the city planning commission, did not return phone calls seeking comment for this story. In a press release announcing the endorsements, Colbruno said OakPAC chose Killian because he "knows the issues facing Oakland and the East Bay and how to get things done."

Killian, a former member of OakPAC who brags on his campaign web site of having co-founded the group in 1999 and serving as its first president, also did not return phone calls seeking comment for this story. Loren Fraser, a spokesman for Killian's campaign, called just before deadline and said the candidate was not available to answer questions over the phone or in person and requested that questions be e-mailed to the campaign. However, as of press time, those questions were still unanswered.

Public records show that Killian's troubles began in the early 1990s when his law practice, Killian & Associates, fell behind on its taxes. By 1996, his unpaid IRS bill had ballooned to $63,932 and the agency placed a lien against him and his property. In all, public records show that from 1992 through 2007, the city of Oakland, the state of California, and the Internal Revenue Service placed at least nineteen liens against Killian and his property totaling $133,574. The most recent lien, signed by Oakland City Administrator Deborah Edgerly, was placed against him by the city on October 17 of last year for failure to pay his garbage bill.

Killian filed for Chapter 13 personal bankruptcy in October 1997, federal court records show. At the time, he told the court that his debts outweighed his assets $235,291 to $139,250. Most of the debts were related to his law practice and for failing to pay taxes, but during the next few months, a host of creditors filed additional claims against him, saying his true debts were actually $825,534.

From the beginning, Killian was not entirely cooperative with the bankruptcy court. In January 1998, the court's bankruptcy trustee filed a notice, saying that when a court-appointed examiner went to Killian's office to review his books, he failed to provide copies of his most recent bank statements even though he was asked to supply them in advance. The examiner also said Killian failed to provide a copy of his latest tax return, his business license, and proof of business liability and worker's compensation insurance. As a result, the examiner said she could not "conduct an accurate examination" of his true financial status.

Once the court accepted his bankruptcy plan, Killian then repeatedly failed to pay his bills on time, records show. The trustee filed documents with the court on at least four occasions, saying his bankruptcy payments were in arrears. It got so bad, that in late 2000 the court ruled that Killian had lost his bankruptcy protection. He later had to petition the court for reinstatement.

Public records show that Killian's former legal secretary, Gloria Clark, and his ex-law clerk, Laurene Somerville, filed the largest claims against him. Clark made a worker's compensation claim for $212,799, alleging that she had suffered multiple repetitive stress injuries that left her incapable of working. Somerville, meanwhile, made a claim for $350,000, stemming from her sexual harassment lawsuit.

In that lawsuit, which was filed on her behalf by the California Department of Fair Employment and Housing, Somerville alleged that Killian routinely told "sexually explicit jokes" in her presence and boasted of his "sexual prowess" to her. She also said that he often screamed profanities at her and once gave her an "obscene" chocolate gift that resembled "female body parts." She also said that after she quit and complained about his actions, he retaliated by writing a letter to the Washington state bar — where she intended to become a lawyer — telling the bar association that she had "poor moral character, was unfit to practice law, and should not be admitted to any jurisdiction."

In court documents, Killian strongly denied Somerville's allegations, and said her work was shoddy and that she had "made false representations" to the court in another case. Killian also alleged that she falsified her employment history and had filed "unlawful termination actions against at least two prior employers." He also said that she responded to verbal criticism by retreating to a corner and shouting, "Oh, please don't hit me." Somerville, who is now a lawyer in Washington, did not return a phone call seeking a response to Killian's allegations.

Eventually, Killian settled both cases, agreeing to pay his former secretary $17,500 and his ex-law clerk $7,000. They likely wouldn't have fared much better in bankruptcy court. The bankruptcy judge had ruled that Killian only had to pay 5 percent of what he owed to each unsecured creditor. In the end, Killian paid a total of $119,500 of his debts before he emerged from bankruptcy in July 2001.

He also settled a debt to his former lawyer, David L. Burg, who said Killian owed him $22,707 for unpaid legal bills. Burg had represented Killian and his ex-wife in a previous case, but Killian refused to pay his bill, alleging that Burg had engaged in legal malpractice. Eventually, Killian lost that argument in arbitration, and then settled the case and agreed to pay Burg $15,000, public records show.

Killian's unpersuasive allegation against Burg was representative of the type of claims he has leveled over the years when he gets in trouble. In 2000, for example, he sued the Alameda County Registrar of Voters, claiming the registrar had incorrectly invalidated twenty signatures he had gathered to qualify for the ballot. The signatures, he said, should have counted even though the voters were registered to vote in another district. Killian also claimed the registrar should have counted last-minute signatures submitted by his campaign.

But then-Registrar Brad Clark told the court that even if he had counted the late signatures — which were handed in ten minutes after the deadline by Killian's friend, Darrel Carey — the AC Transit board member still would have come up seven signatures short of the fifty needed to qualify. Clark also told the court that Killian was wrong — that there were only four signatures invalidated for people not registered as living in the district. The registrar said that most of the signatures — thirteen — were invalidated because the people weren't registered to vote at all.

Author's Note: An earlier version of this story failed to note Killian's fourth council opponent, Frank Rose.