Portland Public Schools Can’t Explain How It Hired a Director With a Prostitution Conviction

"We're trying to understand why," a spokeswoman says.

Last month, Portland Public Schools tentatively offered its general counsel job to a Florida lawyer who had pleaded no contest to violating public records law as the Polk County School Board's attorney in 2009. The lawyer, Wes Bridges, withdrew from consideration after media reports highlighted the conviction.

That hiring flap—PPS had recently been slapped by the Multnomah County district attorney for its slow and improper responses to public records requests—raised questions about the ability of the state's largest school district to properly conduct background checks.

Now, new information in an unrelated personnel case illustrates further blind spots at Portland Public Schools when it comes to vetting job candidates. It has to do with Richard Gilliam, a district administrator who was stripped of supervisory duties months ago after complaints from subordinates.

WW has now learned that Gilliam got his job despite having a 1998 misdemeanor conviction for patronizing a prostitute. That's a criminal history that would disqualify him from holding a teaching job in the state of Oregon.

While Gilliam has been released from his supervisory duties for other reasons, he is currently employed by the district and collects a manager's salary of $87,000 per year ("A Long Recess," WW, Nov. 23, 2016).

District officials are unable to explain how he passed a background check.

"It didn't pop up, and we're trying to understand why," says Courtney Westling, a spokeswoman for the district.

Portland Public Schools officials say Gilliam, who has been the district's director of school and family partnerships since September 2014, passed a background check that included fingerprinting in the summer of 2013, when he was first hired at the district as a community outreach organizer in the Jefferson High School cluster.

PPS apparently didn't find what a straightforward review of public records by WW found—that Gilliam pleaded no contest to the charge of "prostitution" on Jan. 30, 1998—15 years before he sought employment at PPS.

A police report from December 1997, when Gilliam was 36, alleges he paid a woman $20 so he could film her performing oral sex on him in a maroon Dodge Shadow. He had picked her up from a North Portland 7-Eleven, the report said.

In Oregon, a conviction for soliciting a prostitute automatically disqualifies a person from seeking a teacher's license. A no-contest plea is the same as a conviction, although the person making the plea doesn't admit guilt. PPS administrators say central office staff and principals are subject to the same standards as teachers.

But PPS told WW that it can't say whether it knew about Gilliam's conviction—because the district destroyed the record of his background check, including his copy of a form that asks applicants to self-report any convictions.

Westling, the district's spokeswoman, says it keeps records of background checks on employees in the district's archives for only three years, in accordance with state retention rules, due to the high volume of records it processes.

Last month, Gilliam told WW he disclosed the incident to PPS even though he believed it had been expunged. But he also relayed a version of what happened on Dec. 8, 1997, that is at odds with public records WW found.

Gilliam told WW he was visiting Portland from Chicago, where he lived at the time, when he drove past a woman on the street who appeared to have been beaten. He stopped to help her, he says, when suddenly a police officer pulled up and misconstrued the situation. "I was trying to be a good Samaritan," he said in the November interview.

The official police report tells a different story.

According to the report, an officer was on patrol in North Portland around 2 am on Dec. 8, 1997, when he saw a vehicle parked in a location "known to me as a common location for acts of prostitution." He shined his spotlight into the maroon Dodge Shadow and saw a woman "bring her head out of the driver's lap." When Gilliam exited the car at the officer's request, his "pants were totally unzipped," the report continues.

"Gilliam began apologizing, saying that he was not going to insult my intelligence, saying that he had made a very bad decision, that he has never done anything like this before," the officer wrote.

Gilliam was cited and released.

Gilliam maintains his innocence, saying he pleaded no contest on the advice of his attorney and because of "the reality that the word of a black man would not be taken over the word of a white police officer."

He added:  "Unfortunately mine is just one more example of a black man disappointed by the justice system and forced to make difficult choices when wrongfully accused of crimes in the context of a racially prejudiced institution."

Gilliam is no longer a PPS supervisor, but that has nothing to do with this incident. Rather, it stemmed from a personnel investigation into Gilliam's conduct toward employees, whom he had investigated. PPS declined to release those investigations or provide details.

Gilliam's current attorney, Beth Creighton, has said her client planned to pursue a racial discrimination claim against the district.