A New York City councilman once made a female staff member uncomfortable by holding her hand for too long and asking her to wear a beautiful gown to a fund-raising gala.

He told another staff member, who had to go to the emergency room for menstrual bleeding, to “put a Band-Aid on it.”

And he was accused of pocketing $2,000 in cash from a payout to a third staff member and refusing to pay a $15,000 fine imposed by the City Council.

The councilman, Andy King, a Democrat from the Bronx, has long been accused of misbehavior, leading to three ethics investigations by the Council. He might finally lose his job on Monday.

The Council’s ethics committee found last week that the latest allegations against Mr. King were substantiated and recommended his expulsion. The Council speaker, Corey Johnson, agreed that Mr. King should be expelled.

A Council vote is expected on Monday afternoon; if Mr. King is ousted, it could be the first time that a Council member is expelled in a vote by the Council.

“This is not a decision to be made lightly, but Council member King has given us no alternative,” Mr. Johnson said in a statement. “This is the third time this committee has had to discipline the Council member, and yet he continues to show a blatant disregard for the rules and policies put in place to protect staff and the integrity of this body.”

Mr. King’s lawyer, Joey Jackson, disputed the allegations at a news conference on Friday and said that Mr. King was considering his legal options if he was expelled. Mr. Jackson said investigators were out to get Mr. King, ignoring what he said was a history of good deeds for his Bronx constituents.

“It was always an assassination — a character assassination — against a councilman who stands up for his community,” Mr. Jackson said of the investigation.

Mr. King stood silently next to Mr. Jackson on Friday, wearing a face mask and one of his trademark bow ties. Mr. King planned to defend himself at the Council hearing on Monday, Mr. Jackson said.

A two-thirds vote is required to expel a City Council member, something that has not happened since the City Charter was revised in 1989. Mr. Johnson’s office said it believed the expulsion would be the first decided by a Council vote in the city’s history. Other members have been automatically ousted when they were convicted of criminal charges.

Mr. King faced four charges in the latest Council investigation: harassment and discrimination, conflicts of interest, disorderly conduct and violating rules the Council had set for him. When a staff member told Mr. King in September 2017 that she needed to go to the emergency room for menstrual bleeding, Mr. King made the Band-Aid comment and laughed, according to a 68-page report by the ethics committee.

Mr. King was also accused of giving another staff member an extra payment of $9,500 in 2019 and forcing the staff member to give him back $2,000 in cash. Mr. King also failed to pay the $15,000 fine imposed by the Council last year.

The Council voted 44-1 last year to suspend Mr. King for 30 days without pay and to fine him. A motion to expel him was defeated, 34-12.

Investigators had found that Mr. King used Council funds to plan a retreat in the Virgin Islands that coincided with the wedding of his wife’s daughter. Mr. King refused to cooperate with the investigation and sought to thwart it by threatening and firing staff members who he believed were cooperating, the ethics committee found.

In his first ethics investigation in 2018, Mr. King was ordered to undergo sensitivity and ethics training after a female staff member lodged a sexual harassment claim against him.

Mr. King’s predecessor, Larry B. Seabrook, automatically lost his Council seat in 2012 when he was convicted in Federal District Court in Manhattan of orchestrating a broad corruption scheme to funnel hundreds of thousands of dollars in city money to his relatives, friends and a girlfriend.

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