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Monihan was the association’s executive director from 2022 until February. She was briefly a Republican candidate for Senate District 27, and outgoing Sen. Tim Knopp’s endorsee, earlier this year before being disqualified for failing to meet residency requirements.

The lawsuit details alleged interactions between Trowbridge and Monihan beginning Nov. 30, 2023 when the two were left alone after a work-related breakfast, and he made suggestive comments and then allegedly groped Monihan.

Before doing so, Trowbridge told Monihan, “’we make a great team, it excites me to be sticking it to the city, and I really love meeting with you.’ He then added ‘it kind of turns me on,’� the lawsuit said.

Monihan was startled and told Trowbridge his actions were inappropriate, but Trowbridge kept speaking, the lawsuit said.

He allegedly said “’I’m a bad boy. I’m a wild man,’� and kept repeating the latter sentence. Trowbridge also allegedly told her he would deny his conduct if it ever came up.

Roughly a week later, on Dec. 7, a shirtless and apparently intoxicated Trowbridge video-called Monihan from a bed and confessed having feelings for her, the lawsuit alleges. He made a litany of inappropriate comments before disclosing that he was masturbating then turned the camera to show his genitals, the lawsuit alleges.

Monihan quickly ended the call after that, it said.

On Dec. 11, Monihan inquired about the process for reporting a complaint against a direct supervisor, and she was told to speak with Rissa Conway, the board vice president of the Downtown Bend Business Association, the lawsuit said.

In early January, the lawsuit said, Monihan reached out to Conway multiple times without any response.

During that time, Trowbridge allegedly discouraged Monihan from taking two days of vacation and threatened to exclude her from a board meeting, the lawsuit said.

On Jan. 15, Monihan again told the association’s human resources administrator that she needed to file a complaint against Trowbridge, the lawsuit said. This time, she mentioned sexual harassment, to which the administrator said they required legal consultation. Four days later, Conway allegedly told Monihan the association needed to “redefine her position.�

On Jan. 26, Monihan’s daughter who also worked for the association, was fired, and Monihan was placed on a performance improvement plan, according to the lawsuit. Her salary was also docked by $30,000, the lawsuit said.

The lawsuit alleges that, from then on, Monihan’s work was micromanaged she was excluded from meetings and “her ability to finalize grants and generate revenue� for the association was compromised.

She was terminated on Feb. 29, the lawsuit said.

When reached by phone Wednesday, Trowbridge, who owns a business in downtown Bend, was unaware of the allegations. He said he could not respond to the them and proceeded to deny them. He added that the association conducted an internal, independent investigation into him, “and it never went anywhere,� he said.

Rachel O’Rourke, the association’s recently named executive director, wrote in an email that the association “does not comment on pending litigation.�

Conway, the board vice president, confirmed the association conducted an investigation “into Miss Monihan’s allegations which were not substantiated,� she wrote in an email.

Neither Monihan nor her lawyer returned The ÅÝֱܽ²¥â€™s requests for comment.

The lawsuit is requesting up to $1.5 million for the “emotional distress, fear, humiliation, loss of enjoyment of life, inconvenience, and mental suffering� incurred as a result of sex discrimination and a hostile work environment.

Monihan also requested $250,000 for lost wages and benefits.