In 1938, 11-year-old William A. Hilliard applied for a paper route job at the Oregonian. A smart, motivated African American boy with an early love for newspapers and journalism, Hilliard was turned down for the paper route because the truck driver, who did the hiring, thought subscribers wouldn’t take well to having their papers delivered by a black paperboy.

Fourteen years later, in 1952, Bill Hilliard would return to the Oregonian armed with a BA in journalism from Pacific University, and become the newsroom’s first African American employee—as a copy boy. Over the course of more than 40 years, Bill Hilliard would doggedly work his way up the ranks, from copy boy to sports clerk; from sports reporter to general assignment reporter; from assistant city editor to executive editor; and finally, in 1986, as the first African American editor of Oregon’s largest daily newspaper. Hilliard’s career as a newspaperman reached its zenith in 1993, when he was elected the first black president of the American Society of Newspaper Editors (ASNE). He was subsequently honored with a Distinguished Service Award from the University of Oregon and inducted into the Oregon Newspaper Hall of Fame.

But before that—well before the milestones and honors and awards—Bill Hilliard was founder, publisher, and editor of his own newspaper: the Portland Challenger, dedicated exclusively to Portland’s underrepresented black community.

Hilliard with Gov. Holmes and his assistant Harry Swanson at City Desk, April 18, 1958. Allan DeLay

I meet Hilliard at his home next to Forest Park, where he lives with Dian, his wife of 13 years. Hilliard is seated near a large window overlooking Swan Island and the Willamette River. He is 89 years old, and the well-maintained afro he’d worn for much of his adult life is now just a few tufts of black and gray. Diagnosed with Parkinson’s, Hilliard’s voice is soft, his speech halted, and each word he utters comes with palpable strain. But he doesn’t let it quiet him. For nearly two hours, Hilliard shares stories about his childhood in Southeast Portland, his game-changing tenure at the Oregonian, flying all over the world on various assignments, and more. What I’m most curious about is his time with the Portland Challenger. After more than half a century since its brief existence, little documentation or information remains of the newspaper. I want to know what motivated Hilliard—an African American man and a then-recent college graduate—to publish his own newspaper in Portland.

Gabriel Green

“I never saw blacks in the regular daily paper, and I figured we needed a paper that highlighted the good things we did,” Hilliard says. “Because most of what you saw in the [mainstream] paper was crime.”

Portland in the 1950s was very much a segregated city. After the flooding of Vanport in 1948, black families were relocated to the Albina district in Northeast Portland. Owing to discriminatory real estate and lending practices, African Americans were essentially confined to this narrow area, while white families moved to whites-only suburbs. Segregation in Portland at that time was sanctioned and enforced.

“There was a theater on what is now Martin Luther King Jr. [Blvd.]—used to be Union Ave—called the Egyptian,” Hilliard says. “Blacks had to go upstairs in the balcony, they couldn’t sit on the main floor. I never went in the theater. Never went in there at all. I refused to patronize segregated places.”

Though the rest of the city discriminated against African Americans, for a brief stint Albina—especially along North Williams—was home to a thriving black community, with jazz clubs, record stores, clothing boutiques, pharmacies, and restaurants. And it was on the corner of North Williams and Cook that the Portland Challenger printed its first issue on May 6, 1952.

“It is the hope of the Challenger,” Hilliard wrote in his inaugural editor’s note, “through its news and editorial columns, to hasten the day of integration and to foster the principles of true American democracy.”

The first issue arrived on an election year, and the Challenger examined who was running for various offices and their opposing positions. African Americans, according to a national poll published by the Challenger, favored incumbent president Harry S. Truman, who ultimately lost in the primaries against Adlai Stevenson.

Hilliard enlisted people he knew to contribute to the paper, many of them childhood friends and other recent college grads. Hilliard assumed the role of editor and publisher, with Lonnie Harris as sports editor, Louis Fuller Jr. as staff artist, Joy Brock as staff writer, and Ted Wesley Burger as managing editor. Hilliard also brought on board Richard “Dick” Bogle, who grew up on the same street as him and attended the same grade school: Southeast Portland’s Hosford Elementary. Bogle would go on to become an officer with the Portland Police Bureau from 1959 to 1968, and then became the first black television news anchor on the west coast, at KATU, where he stayed for 15 years. In 1984, Bogle was elected to Portland City Council. In his final years before passing away in 2010, Bogle was a contributor to Down Beat magazine and hosted a weekly jazz show on KMHD. But the 22-year-old Bogle hadn’t yet received his journalism degree from Portland State when Hilliard tapped him to become associate editor of the Challenger.

The inaugural Portland Challenger inside Hilliard’s personal scrapbook. Gabriel Green

Though several of the newspaper’s contributors would go on to become formidable leaders in their own right, many of the bylines were at the time unknown names—just folks from down the way. Dr. DeNorval Unthank—the only black physician in Portland in the 1930s, and the first black member of the City Club of Portland—lived with his family in the same Southeast neighborhood as Hilliard. Dr. Clarence Pruitt—the first African American to graduate from and teach at the University of Oregon Dental School, now OHSU School of Dentistry—was Hilliard’s dentist. Each of them lent a hand in supporting Hilliard’s fledgling newspaper.

At Hilliard’s house, original copies of the Challenger are preserved in a large, black folder, which Dian retrieves from their basement. As I flip slowly through the pages, she points out an article in the sports section, accompanied by a black-and-white photo of a smiling, handsome, young black man in a football jersey.

“Oh, there’s Emery,” she says to Hilliard, with a laugh. “Oh, you just wrote about all your friends!”

Emery Barnes was Hilliard’s roommate at the University of Oregon. After a brief stint with the NFL, Barnes moved to Canada to escape racial discrimination in the US. He entered Canadian politics, focusing on social welfare and human rights, and became the first African American elected to a legislative office in British Columbia. Barnes then went on to become the first African American elected to Speaker of the Legislature in 1994. The city of Vancouver, BC, named a park after him.

Dian notes how all of these old friends became the “first” African Americans in their fields. Hilliard attributes it to the fact that his grade school, unlike many other schools in Portland, had been integrated. He believes that attending an integrated school gave him and his friends opportunities other kids missed out on. But even with opportunities, support, and intelligence, Hilliard, as a black man, had to have twice as much drive as his white peers, and put in three or four times as much work.

His life as a newspaperman was determined almost from the beginning.

Allan DeLay

After being turned away by the Oregonian for a paper route, 11-year-old Hilliard went door-to-door, selling the Saturday Evening Post and other magazines. He worked on his school newspaper at Benson Polytechnic High School, and at 18 was drafted into the US Navy, where he served one year before being discharged Seaman First Class. He went on to study journalism at Vanport Extension Center college (now Portland State University), then transferred to the University of Oregon. When a white professor took Hilliard aside to let him know that a black could never hope to find work at a major newspaper, Hilliard left U of O and transferred to Forest Grove’s Pacific University, where he became managing editor of the campus newspaper, The Pacific Index, and was elected editor for the 1951–52 school year. After graduating from Pacific, he was offered an internship at the Hillsboro Argus—and shortly after, he launched the Portland Challenger.

The Challenger covered the NAACP and Urban League meetings when other newspapers wouldn’t. They offered political candidates’ positions on civil rights. They published stories on local sports, dances, and other social gatherings within Portland’s black community. When Charles Gragg and his wife Joyce moved to Parkrose Heights, then an all-white neighborhood, the couple awoke one morning to find a burning cross on their lawn. Hilliard put this story on the front page of the May 20, 1953 edition. “I am determined to stay,” Gragg was quoted as saying. “This is a challenge.”

Oregon passed its civil rights bill on April 13, 1953—the 21st state in the union to pass such legislation—and the Challenger marked this historic occasion with a celebratory front page story, printing the three sections of the new law word-for-word.

Publishing a newspaper wasn’t easy, however, and it wasn’t cheap. Like most periodicals, the Challenger depended on advertisements, mostly from other Albina businesses, like Benny’s, Wilson’s shirt shop, Hooson’s Hardware, and Phil Jones Food Market. Hilliard had to hustle for every one of these small ads, and even then the paper—which Hilliard estimates to have had a circulation of 4,000 to 5,000, at 10 cents a copy, or $2.50 for a yearly subscription—struggled for revenue. To help support himself and the paper, Hilliard worked at Union Station as a railroad porter, known back in the day as a “redcap.” There were about 50 redcaps at Union Station, almost exclusively African American men. Each redcap was assigned a number, which would identify him and connect the passenger to his or her luggage. Hilliard was number 28.

“You had a great big cart full of bags, and you’d go out front to deliver them,” Hilliard explains. “People would pick them up, and that’s when they’d tip you. But you didn’t get much in tips. If you had two bags, they’d give you a quarter.”

Hilliard faced resentment from his white bosses at Union Station. They couldn’t figure out why a young black man with a college education would want to work part-time as a redcap. But to Hilliard, it was a necessity to keep the Challenger afloat.

“Being a redcap gave me the opportunity to work on this sort of paper, which was very independent of the big papers,” Hilliard says. ..“And the white guys, they didn’t understand that.”

To further supplement his income, Hilliard also worked as a copy boy at the Oregonian. He didn’t harbor any resentment against the paper for their snub 14 years prior—or, if he did, he didn’t let it deter him. Even so, he didn’t get the job on his first attempt.

“They said they wouldn’t hire college graduates to do copy boy work,” Hilliard says. “They wanted someone with experience. I said I can’t get the experience unless you give me the opportunity.”

Hilliard was hired by the Oregonian on his second try. He was 25 years old, the first black employee in the newsroom. He didn’t remain a copy boy for long, however, and within a year he was given his first writing assignment. Hilliard smiles as he remembers his debut as an Oregonian reporter.

“The first story I had was about an old black man who was a hundred-and-something years old,” he says. “I thought everybody around Portland would see my name and pay attention.”

Meanwhile, the difficulties in maintaining the Challenger proved too great to continue. Hilliard had been publishing the paper, writing most of the copy, and drumming up advertisers, and even with his supplementary work at the Oregonian and Union Station, the paper’s funds soon dried up. The Portland Challenger printed its final issue in the spring of 1953, only a year and a half after its debut. Though Portland’s black community lost a promising new voice, Hilliard was now free to commit himself fully to the Oregonian.

Gabriel Green

He worked myriad beats, earning promotions to sports reporter, religion reporter, and general assignment reporter. In 1965, he became assistant city editor, and in 1971 he was named city editor—an event that was noteworthy enough to be covered by Time magazine. Under his management, the Oregonian became the west coast’s first newspaper to cover the national meetings of the NAACP and the National Urban League. Hilliard prohibited writers from the use of racial identification unless it was critical to the story, because it reinforced negative stereotypes.

“After the Watts riots, a lot of white-owned papers began to look for black writers,” Hilliard says. “And I was a prize for most of them, because I’d been working at the Oregonian for years as a reporter, covering all kinds of stories, all around the country. And when they began to see me, they thought that I’d be a good one to start with, but I never left the Oregonian. I wouldn’t leave. The Oregonian was good to me, gave me an opportunity, so I decided I owed it to them to stay. So I did stay, and it’s a good thing I did.”

Hilliard was named executive editor in 1982, and one of his first responsibilities was the impending merger of the Oregon Journal with the Oregonian, which gave the paper even greater leverage and boosted circulation. Five years later, in 1987, Hilliard was offered the paper’s top job, becoming the first black editor of the Oregonian. As head boss of the newspaper, Hilliard increased the hiring of non-whites, broadened coverage of minority and LGBT issues, and delivered lectures throughout the country on the importance of diversity in the newsroom.

In 1992, following protests by Native American communities across the nation, the Oregonian became the first major newspaper to bar sports teams with names that were derogatory to Native Americans. Not everyone at the paper was on board.

Bill Hilliard at his desk, July 22, 1959. Many Oregonian reporters grew beards in honor of the Oregon Centennial. Allan DeLay

“The sports editors were nasty about it,” Hilliard says. “And I threatened to remove them if they didn’t go along with the policy. They said, ‘You can’t say Washington unless you say Redskins.’ I said, ‘The hell you can’t. I’ll sit down at the typewriter and show you what to do.’ And all I did was just use ‘Washington’ or ‘Atlanta,’ and that was it.”

The Oregonian has since rescinded this policy. [CORRECTION: The Oregonian's director of news, Therese Bottomly, has told the Mercury that this policy, in fact, still stands. Former sports editor Jeff Wohler also takes issue with this description, saying that neither he, or his editorial assistants, were "nasty about it" and they implemented the new policy when asked to do so.]

Also in 1992, the Oregonian endorsed a Democratic candidate for president for the first time in its history.

“Clinton called one day, and wanted to come in to meet the editorial board,” Hilliard says. The publisher, Fred Stickel, wasn’t a fan of Clinton, so Hilliard invited Stickel to sit in on the meeting. Stickel walked away impressed with what he’d heard from Clinton, and gave Hilliard the go-ahead for the endorsement. Bill Clinton won Oregon with 42.5 percent of the vote (over George H.W. Bush’s 32.5 percent and Ross Perot’s 24 percent).

The following year, the 65-year-old Hilliard was named the first black president of the American Society of Newspaper Editors. In an interview with the New York Times marking the occasion, Hilliard said, “The thing that bothers me more than anything else, is what I see as more and more racial divisions in the country today. And I think newspapers are the ideal educational tool to correct it.”

At the end of his one-year term as president of the ASNE, and after 42 years at the paper, Hilliard retired as editor of the Oregonian.

“When I retired, Bill Clinton gave us a party inside the White House,” Hilliard says. “We had a ball.”

Hilliard in recent times, with wife Dian. Gabriel Green

As Hilliard tells me these stories, it’s November 7, one day before the 2016 presidential election. I want to know, after everything he’s seen, what he makes of the Republican candidate.

“Trump was telling people that he’s going to arrest the liars at newspapers when he gets to be president,” Hilliard says. “It’s a bunch of crap he’s giving people. But eventually, if we’re not careful, we could be like [Nazi Germany]. It scares the hell out of me that one of these days we’ll end up with a dictator.”

For one who has spent his entire adult life in the newspaper business, and as a lifelong advocate for diversity in the newsroom, a Trump presidency is a serious concern—not only to Hilliard, but to journalists across the nation. Journalism has been under threat for years, but it faces an even greater menace under a Trump administration. What opportunities Hilliard had been given were not available to everyone—nor are they guaranteed to anyone today. His success didn’t only come about through hard work and perseverance, but from hard-won civil rights, desegregation, and the commitment to diversity in schools and the workplace. For any American committed to freedom and equality, a free and open press is an indispensable tool in ensuring equal opportunity and fairness. As Hilliard wrote 64 years ago, in the first edition of the Portland Challenger, a newspaper’s main objective is to “foster the principles of true American democracy.”

Like the country itself, Portland has seen numerous changes since Hilliard was a young, ambitious, black reporter working the beat. Though we’ve still got a long way to go, Portland has become a more welcome and diverse city, thanks in large part to Bill Hilliard’s long and dedicated life as a newspaperman.

“I want to believe,” Hilliard said at an ASNE meeting in 1994, “that over the years, scores of young people of color have looked at me and said, ‘It can happen.’”

Hilliard and Johnny Cash. Photo Provided by the Oregonian