More than a year before a veteran coach pleaded guilty to physically harassing another staff member, a Portland Public Schools principal emailed top district officials to warn that decades of complaints about Mitchell Whitehurst's "over friendliness" with students and colleagues could lead to scandal.

"For the past 30 years, there have been rumblings about Coach Whitehurst," Faubion K-8 principal LaShawn Lee wrote in January 2013. Lee then invoked a notorious sex abuse and coverup case involving a longtime college football coach.

"I'm extremely concerned about this becoming a 'Penn State University' scandal," Lee wrote.

The email was among dozens of pages of court documents released Monday, part of a $650,000 lawsuit filed against the school district last fall by the victim in the harassment case. That employee, whom The Oregonian/OregonLive is declining to name, accused Whitehurst of creeping up behind him while he was talking to another teacher and inserting "his finger or some other unknown object in, on or around (the employee's) anus."

The documents shed new light on how officials handled years of allegations from students and staff about sexual misconduct by Whitehurst. They allege inquiries either went nowhere or never started at all, with the district unable to explain its efforts to investigate complaints from students and staff.

Among the new details in the court documents, filed after the district asked a judge to decide the case without a trial:

• Starting in 2008, a former student twice tried to report allegations of sexual misconduct from as early as 1983, saying Whitehurst asked her and her friend to perform oral sex, the documents say. The district checked to see whether the former student and Whitehurst were at the school at the same time, the documents say, but then did nothing else.

• In 2001, a student working as a classroom aide made a report, which is not public, of sexual misconduct against Whitehurst.

• In 2013, female students at Faubion, a Northeast Portland school with students from kindergarten through eighth-grade, boycotted Whitehurst's gym class — prompting Lee's email. They said he stared at them sexually, called them pet names, made remarks about their bodies, videotaped them, and, in one incident, had a girl pick up a ball while he stood behind her, the documents say.

Lee wrote she was "extremely conflicted" about allowing Whitehurst to remain on campus during an investigation. The district ultimately found the accusations "unsubstantiated," the documents say.

A spokeswoman for the district declined to answer several questions from The Oregonian/OregonLive about Whitehurst's more than 30 years with the district and how the district investigates and tracks abuse complaints, citing pending litigation.

"We of course take student safety seriously," spokeswoman Courtney Westling said. "We understand why there are questions being asked in light of this lawsuit, and we are responding to the allegations in state court. Because of that, we not able to respond to all of the detailed questions presented at this time."

Portland Public Schools has taken issue in court filings with the employee's characterization of the allegations over the years and has said, while it received information about Whitehurst, the district acted appropriately under the circumstances.

Attempts to reach Whitehurst on Thursday were not successful.

"This is all part of a systemic problem of not acting appropriately when information about dangerous things or people come to light," said Matthew Ellis, the attorney for the victim in the harassment case.

Ellis said he was particularly disturbed that a former student complained and the district investigated enough to find it was plausible, only to drop the issue.

"You don't do an investigation, realize it might go somewhere and go 'uh oh' and stop it — especially when the concern is sexual assault of children," Ellis said. "They seem all too willing to stick their head in the sand that's just intolerable."

Whitehurst was allowed to retire last year even though the district's investigation into the harassment case concluded he engaged in "inappropriate, unprofessional and unwarranted conduct of a sexual nature."

But when the Oregon Teaching Standards and Practices Commission investigated Whitehurst after his conviction, it found him unfit to teach and revoked his license in January. That decision was based in part on a fresh investigation of allegations of sexual misconduct from the 1980s. The commission's report noted Whitehurst denied the allegations.

District officials first learned of those allegations in 2008, court records say. Beyond accusing Whitehurst of asking for oral sex, the former student said he told her and a friend he wanted to watch them kiss and took them to his apartment complex.

Five years later, when the former student was working for Portland Public Schools as a substitute teacher, she reported the accusations again, the documents say.

Complaints from Faubion students about Whitehurst, also in 2013, prompted Lee, then the principal, to email senior administrators, including the district's top attorney.

In raising her concerns, Lee also referenced a 2011 incident at Jefferson High School, where Whitehurst was working as athletic director. The court documents say someone had hung posters at the school, and in the community, calling Whitehurst "a pedophile."

"Even though the reports were made directly from students with firsthand knowledge of the conduct and based on the feelings and perceptions they had, (Portland Public Schools) concluded the complaints were 'unsubstantiated,'" the documents say.

School employees are mandatory reporters, meaning Oregon law requires them to report suspected abuse of a child to law enforcement.

The employee in the harassment case spoke with police, including a student resource officer assigned to Faubion who repeatedly promised him, "we're going to do it right this time," the documents say.

It is unclear if the district ever worked with law enforcement on other allegations and the district refused to say.

The Oregonian/OregonLive also asked what policies, procedures and training the district has in regard to sexual misconduct. The district refused to detail these polices, but said they existed.

The employee in the harassment case had previously had two other incidents of unwanted contact with Whitehurst, who was known to slap coworkers on their buttocks, according to court the documents.

According to court filings, Lee witnessed Whitehurst slap another employee on the rear and wrote him a formal memo to stop, according to the plaintiff's filing. Despite the memo, the documents assert the district considered Whitehurst's "horseplay."

Whitehurst also worked as a coach at Lincoln and Marshall high schools, according to past Oregonian stories. Whitehurst received 18 months' probation for the harassment case and was never charged with a sex crime.

"This is all part of a systemic problem of not acting appropriately when information about dangerous things or people come to light," Ellis said. "You don't get to stick your head in the sand and claim you didn't know about it when you've got somebody who is a known risk."

-- Bethany Barnes