City councillor Craig Kelley

Two efforts to address Cambridge legal issues failed Monday in City Council votes — both brought forward by councillor Craig Kelley and ending with him standing mostly alone.

The first asked for direct control of Law Department funds instead of letting it become just another line item in the city budget overseen by City Manager Robert W. Healy. There were five votes against; councillor Sam Seidel voted with Kelley, and Ken Reeves and Denise Simmons abstained or voted present.

The second policy order was more complicated: It would have asked Healy to ask the city’s own lawyers to extend the deadline for the city to sue them for bad advice. It pertains to Malvina Monteiro v. City of Cambridge, which began some dozen years ago and claims Healy fired Monteiro from her role as executive secretary of the Police Review and Advisory Board for complaining about racial discrimination. In this case, with a potential $10 million at stake that includes an initial finding Monteiro was due $1 million in compensation and $3.5 million in punitive damages, the city is represented by outside counsel rather than staff from its Law Department.

On this second vote, Reeves and Simmons again voted present, but Seidel joined the majority in voting no.

The technical deadline for the lawyers to extend the statute of limitations to be sued was Sunday, and Healy confirmed after leaving the council meeting that there had been no actions taken over the weekend, meaning the lawyers had not been asked to extend the deadline and had not taken the action on its own.

Councillors were skeptical about Kelley’s order, with Reeves saying it was “a completely novel legal theory that you would get an existing law firm to waive” its protections against liability. But it was the city’s attorney in the initial case and current appeal, Joan A. Lukey, who mentioned reducing Monteiro’s punitive damages because he hadn’t acted recklessly in the case, but instead had “prudently sought the regular advice of counsel.”

“Willing to live with the decision”

Henrietta Davis had used her “charter right” powers to cut off conversation about Kelley’s order when it was introduced last week. When it was taken up again Monday, after the deadline, she and Simmons wanted Kelley — who has a law degree from Boston College — to explain its point, which he said “was a request to keep a ‘what if’ alive. It wasn’t even legal advice. It was simply asking that we keep our options open, and I’m not sure what the problem is.”

Mayor David Maher had an answer.

“I’ve spoken with a number of lawyers who were just shocked by this and that it would be brought forward [and said] no law firm in their right mind would sign on,” Maher said. “This does not seem prudent or wise to me.”

He seemed impatient with Kelley, a frequent outlier on council issues, and called the effort “chasing our tails around in circles” before suggesting any competent lawyer would laugh at the suggestion and tell the city to find other counsel.

But he shared the view of several others in the room in wanting the 12-year-old case to simply come to an end. “I’m willing to live with the decision that comes from the courts,” Maher said.

Reeves agreed, saying it was time “to act logically on what has been rendered” in a matter that has been a minus for the city.

Resident Margaret McMahon indicated she backed Healy in the initial case, but called the continued appeals “foolish and expensive and unworthy of Cambridge. Let’s stop this thing right away, man up and pay.” Elie Yarden called the case “a waste of millions from the public trust,” and  Charles Teague said, “I just want this to be over.”

The case has cost the city more than $2 million in legal fees, and during the appeal the city’s damages to Monteiro have ballooned with interest to a potential $7.3 million. Resident Richard Clarey, an attorney, said the cases of two women with complaints like Monteiro’s arrive in court in August.