It was the moment Portland School Board member Paul Anthony had been waiting for.

On Jan. 26, on a table in Superintendent Carole Smith's office, Anthony placed evidence of a serious problem—the marked disparities between the classes Portland Public Schools offers white students and those it makes available to their black and Latino peers. He showed Smith spreadsheets indicating students at predominantly white schools were getting as much as three times as many course options as schools where most students are black or Latino.

Anthony asked Smith to take a closer look at the numbers.

"She wiggled her fingers at them and giggled and said, 'I know all about them,'" Anthony recalls. "She completely fails to get the point."

Now Anthony has raised the stakes: On May 26, he filed an incendiary complaint with the federal government. In the complaint, newly obtained by WW, Anthony alleges that poor, black and Latino children, as well as immigrant kids, don't get the same quality education as rich, white kids in the city.

"Access to school programming in Portland Public Schools is disproportionately determined by race and national origin," Anthony says in the complaint.

Anthony is asking the U.S. Department of Education's Office of Civil Rights to intervene in how Portland distributes school funding. The feds hold the purse strings for millions of dollars in education funding. Anthony is asking them to step in—and ultimately to withhold money unless PPS corrects what he sees as civil rights violations.

It's not unusual for someone to complain about school inequities to the feds. But it's rare for a sitting school board member to file such a complaint against his own district—and especially against a superintendent who has made "equity" her byword.

Anthony says he has no choice but to take his case to the feds: "The issue is too important. I went to the feds because I could not get anyone to take the issue seriously."

Smith declined to comment on the specifics of Anthony's complaint, instead saying in a statement, "I'm not going to use the media to address concerns from individual board members."

She also notes that the district's budget was subjected to a public vetting before approval.

"It was a very public process in which the board had the opportunity to make amendments, and they ultimately adopted it," she notes. "My door has always been open and remains open to discussing the concerns of individual board members."

Anthony's complaint adds to the troubles of a beleaguered Smith, who also faces an investigation into the district's handling of lead testing of school drinking water. He's also the only School Board member to call for her resignation in the wake of the lead scandal.

Anthony's decision to file a civil rights complaint has drawn criticism from some of his fellow board members.

"I wish he hadn't done that," says Pam Knowles. Steve Buel is still deciding what to make of Anthony's complaint. "I think it's an interesting move—basically you're suing yourself in a way," Buel says. "It shows a little frustration with the School Board and the administration."

He's an unlikely figure to play Public Enemy No. 1 of the state's largest school district.

Anthony was elected to the School Board last year as part of a wave of dissatisfaction with Portland Public Schools' leadership. He started as chairman of the Humboldt Neighborhood Association during the fight over closing the Humboldt K-8 School in North Portland and as a parent activist when he saw problems at Beach K-8.

"He's one of the smartest people I've ever met," says North Portland schools activist Rita Moore. "He's almost certainly the hardest-working person I know or at least very high up there on the list. He's remarkably persistent. He does his homework. When he says something, it's because he thought about something and he's researched it."

For much of this year, Anthony has been a voice of dissent but not a rabid one. After weeks of bad news about lead in the water, though, that changed. When the superintendent announced she was retiring but would stay on until next June, Anthony demanded she leave sooner.

Similarly, he has lost faith that PPS can correct the disparity in course offerings without a push from the outside.

At high-poverty George Middle School in North Portland, where just over half the students are black or Latino, kids can choose from 27 classes. At predominantly white West Sylvan Middle School on the westside, students pick from 55 different courses.

At Harrison Park K-8, one of the most diverse schools in the city, students in the middle-school grades have six electives—while students at nearby, whiter schools get as many as 11 electives.

"That's not an OK thing to be giving the kids at Harrison Park," he says. "They're serving a desperately poor community."

The complaint asks the Office of Civil Rights to force the district to fix the inequity.

Anthony's complaint has yet to move to a formal investigation, a process that generally takes 30 days but can sometimes take much longer, U.S. education officials say. Investigations can sometimes drag on for years, but they can also be highly effective at getting school districts to act because of the threat of lost funding.

Currently, the Education Department's civil rights division is formally investigating 15 separate complaints about PPS, including two filed by parent activist Kim Sordyl over a series of contracts for services aimed at kids on the basis of their race and in some cases their gender. (It's illegal to discriminate on the basis of race, ethnicity or gender, even if the intent is to help at-risk kids, Sordyl argues.)

In years past, the department has reprimanded the district for its handling of a student government election at Sellwood Middle School and a principal's race-based investigation of a theft.

In fiscal year 2015, the department's Office of Civil Rights received 10,400 complaints nationwide, investigated 3,000, and found in one out of three of those cases at least some civil rights problems.

PPS has received upward of $50 million in funding from the federal government in years past, all of which could be at risk if the complaint is upheld and the district fails to act.

Anthony is resolute in his plan to make a federal case out of inequity. "It's not like they're going to silence me just because I'm on the board," he says.