Portland Public Schools has settled with a one-time acting superintendent and former chief operating officer who was ousted in 2017 after being accused of having an illicit relationship with a subordinate.

Yousuf Awwad, who was dumped as the district’s second-in-command by newly hired Superintendent Guadalupe Guerrero in November of that year, will receive nearly $350,000 to settle the wrongful termination suit he filed last year. Charese Rohny, the attorney who represented Awwad, received $327,525.

Awwad’s suit claimed, among other things, that then-board chair Julia Brim-Edwards launched an investigation into his conduct and hired a lawyer to lead it without a public vote, in violation of public meetings law, and that Brim-Edwards was motivated against him by racial animus and because he rejected her supposed bid to become superintendent.

Brim-Edwards has denied the allegations and in a statement said the school board has an obligation to “manage, evaluate, review and investigate material issues" related to the district’s superintendent and that the school board received “several, serious allegations” during Awwad’s tenure.

Under the deal, struck in July, Awwad received about half the money — $172,475 — this summer. The remaining portion of his award, $175,000, will be paid to him over the next 10 years at a rate of about $19,000 a year. The Oregonian/OregonLive obtained a copy of the settlement agreement through a public records request.

Spokesman David Roy said the $675,000 payout won’t come out of district coffers but is instead covered by its policy with Genesis Insurance. Because the settlement decision was made by an insurance company official, the deal was not brought up for a public vote by the school board.

Awwad filed the suit in August 2018, weeks after The Oregonian/OregonLive reported on a three-page investigative memo that said that although the then-deputy superintendent of Portland Public Schools had not broken any policies in dating a subordinate, he had exercised poor judgment by signing off on a raise that the woman’s supervisor awarded her and failing to disclose the relationship to anyone but interim Superintendent Bob McKean.

At the time he fired Awwad, Guerrero said he was exercising his right to choose his own deputy with the “right fit.” And Brim-Edwards said Guerrero’s decision was separate from the board’s investigation into possible nepotism and that the board did not call for the firing.

“The board had a fiduciary duty to investigate the allegations in a thorough and fair manner, which it did," Brim-Edwards wrote to The Oregonian/OregonLive as an individual outside of her role with the district.

Prior to Guerrero’s taking the helm of Portland Public Schools, Awwad was one of few top-level staffers who weathered a turbulent time that saw a high level of churn. He served as interim superintendent until Guerrero was hired in fall of 2017, a time during which Awwad was meant to act as a steadying hand for the district as the school board recruited a new top administrator.

But just weeks before classes started that year, Awwad was under investigation after a series of anonymous complaints surfaced about his relationship with a subordinate. Awwad said he was adhering to district policy by disclosing the relationship to his supervisor, McKean, a claim that an external investigator later vindicated.

District officials declined to comment on the settlement with Awwad beyond prepared remarks contained in the document.

“We have reached a settlement with Yousef Awwad who has served as CFO, deputy CEO and interim Superintendent for PPS during challenging times. We appreciate all his efforts on behalf of the district’s students, and we wish him much success,” the district said in a statement.

Awwad similarly provided a statement within the settlement document.

“I am proud of the work I did for Portland Public Schools and honored to have had the privilege of serving Portland’s students. I wish continued success to the district in fulfilling its critical mission in this community,” he said.

The size of Awwad’s six-figure settlement is reminiscent of payouts Portland Public Schools regularly provided ousted administrators nearly two decades ago.

Those golden parachutes were once baked into the contracts of top administrators, including former Superintendent Ben Canada, who received a $260,000 buyout upon his dismissal. Deputy Superintendent Susan Dyer, who was pushed out after just seven months on the job in 2001, received $238,000.

“Those outraged people because, essentially, the district reached agreements to pay people outside of litigation large sums of money,” Brim-Edwards told The Oregonian/OregonLive.

She spoke about previous settlements outside of her role with Portland Public Schools and instead as an observer of both past and present district practices.

When she ran for the school board in 2001, Brim-Edwards pledged to eradicate those six-figure payouts. And the district did indeed stop baking an offer of a golden parachute into its contracts with top administrators.

Brim Edwards took a 12-year hiatus from the board after that initial term in office. She won another term in 2017 and was instrumental in Guerrero’s hiring.

In November of 2004, Brim-Edwards and then-Superintendent Vicki Phillips asked human resources chief Steve Goldschmidt to renegotiate his contract, which included a $357,000 severance unless he was fired for causes involving moral turpitude or gross neglect of duty.

Goldschmidt did not respond to the request and Phillips fired him in 2006, claiming gross neglect. An arbitrator later ruled against Phillips, citing a shining evaluation from a previous superintendent and a lack of evidence for her claim.

The arbitrator awarded Goldschmidt $620,000.

Those funds, similar to Awwad’s, were paid by the district’s insurance.

“In this particular case,” Brim-Edwards said, “employment cases can be long and it was the insurance company’s decision to settle as it was paying for the settlement.”