The city has already paid more than half a million dollars to settle claims involving the outgoing official.

Updated 3:43 p.m.

One of Philadelphia Sheriff Jewell Williams’ highest-ranking female deputies is suing the city after her boss allegedly attempted to sabotage her marriage, retaliated against her, and subjected her to workplace humiliation.

This is the latest of at least six civil rights claims naming Williams for his alleged misconduct as an elected official, all with similar themes that have appeared in those suits. The city has paid out $587,500 to settle past cases that involved the sheriff, according to the city’s Law Department.

In the latest suit, filed in the U.S. Eastern District Court on Tuesday, First Deputy Sheriff Jennifer Algarin-Barnes alleges Williams threatened to put her on the “11 to 7” shift “just to see what it would do to her marriage.” Algarin-Barnes also alleges that at one point her boss suggested he would leave her after she turned 50.

“No one wants a broken-down woman,” Williams told Algarin-Barnes, according to the lawsuit.

Williams, who lost the Democratic Primary to challenger Rochelle Bilal in May, has denied wrongdoing in every case and maintains that the city settled past legal charges against him without his knowledge. Asked for comment on the allegations, Dan Gross, a contracted spokesperson for the office, referred questions to the city. After publication of this article, Williams emailed Billy Penn a statement.

“All of these allegations are false, and I am awaiting my day in court so the truth can come out,” Williams said. “These days anyone can make any accusation against anybody and because they see other settlements, they think they can get a quick payday by bringing a lawsuit. Let’s go to court so the truth can be heard.”

A spokesperson for Mayor Jim Kenney condemned Williams in the wake of the latest suit.

“The Mayor has long called for Jewell Williams to resign because of the abhorrent conduct that led to past civil settlements,” spokesperson Mike Dunn told Billy Penn. “We look forward to working with Sheriff-elect Rochelle Bilal after her inauguration in January.”

While Williams may be on the way out, the new legal filing hints that his alleged misbehavior could keep costing taxpayers for years to come.

The lawsuits against him have all featured similar claims of retaliatory, discriminatory or sexual misconduct since he took over the office in 2012. One former female sheriff’s employee alleged Williams took out his sexual frustrations on women in the office, another former staffer said Williams encouraged him to kill himself.

Williams has pointed to his promoting of a women up the ranks in the sheriff’s department as a defense against harassment and retaliation claims. He named the office’s first-ever female deputy sheriff in 2015.

That very deputy, Dolores Ramos, has also sued Williams. She filed legal claims over “severe sexual harassment by her supervisors” and subsequent retaliation. Those claims mostly involved a supervisor whom Williams had promoted; the city settled the case earlier this year for $430,000.

‘After I get re-elected…it’s on’

Algarin-Barnes’ lawsuit follows a June complaint filed with the Equal Employment Opportunity Commission. In that legal filing, Algarin-Barnes said Williams blamed her and others in the office for his loss in the May primary. She said Williams faulted employees for not defending him publicly amid sexual harassment allegations.

In her newly filed civil rights suit, Algarin-Barnes paints Williams as a cruel and petty supervisor who targeted her entire family with threats.

In one instance, Williams allegedly sought Algarin-Barnes out to gossip “derogatorily” about office romances, and targeted her when she refused to indulge his whims, according to the suit.

Williams, the lawsuit alleges, “got pleasure” in promoting the woman “so that she would make more money than her husband.” The lawsuit also claims Williams targeted Algarin-Barnes’ son, who also works in the sheriff’s employee, with false accusations.

The suit claims Williams had been threatening the jobs of both Algarin-Barnes and her son even prior to his election loss, suggesting that “pink-slips” were coming for employees who did not do his bidding. Williams has a history of asking his employees for campaign contributions and other political favors.

“There are going to be some changes around her after — after I get re-elected…it’s on,” the suit claims Williams said.

Employment attorney Steven T. Auerbach, who represents Algarin-Barnes and other employees in lawsuits naming Williams, declined to comment on Tuesday.