Raymond Duncan Shoemaker, (1894-1977) hardly fit common stereotypes of a political radical. Yet in 1959, this respected judge accused local police of attempting to run Portland, Oregon like a police state, igniting a public feud sixty years before Black Lives Matter dragged law enforcement accountability into the national conscience. It was no singular outburst, but instead represented one fair minded man’s long time effort to enact social justice from within the legal establishment.

Raised near Glasgow, Montana, Shoemaker never cut an imposing figure, with a slim build and standing only 5’6” tall. Still, he gravitated towards heavy industries, employed on local cattle ranches and the Great Northern Railroad in his youth before traveling to Colorado where he labored in the Durango gold mines. Already curious about different peoples and cultures, he spent time learning Spanish from his co-workers. By 1916, at age 22, Shoemaker returned to his home state and joined the 2nd Helena, Montana contingent of the National Guard shortly before their deployment into Mexico during what became known as the Punitive Expedition.

This came about following many decades of political coercion and military conquest, through which the United States reduced Mexico’s territory by about 50%. Unsurprisingly, economic and social turmoil became common during those years, culminating in the Mexican Revolution (1910-1920). Various political factions and figures colored that conflict, but none more famous than the insurgent leader Pancho Villa.

Villa naturally considered the border an illegitimate boundary and didn’t restrict military operations below it. The US government also ignored borders when convenient, most notoriously with its invasion and occupation of Veracruz in 1914. Then in 1916, Villas’s troops raided the town of Columbus, New Mexico, creating mass public outcry for vengeance. Subsequent National Guard mobilization eventually pulled young Ray Shoemaker far from home on a futile chase that drew US soldiers deep into hostile territory.

Shoemaker learned much from the experience. His Spanish fluency proved useful communicating with locals and only furthered a fascination to explore other cultures. He remained in military service through World War I, earning the rank of corporal. All these life experiences made him what people in those times called a Free Thinker.

This loose term encompassed many political stances later considered liberal, such as opposing racism, advocating for women’s rights, supporting organized labor, and deep religious skepticism. He avidly read leftist and anti-fascist literature, including the Little Blue Book series published by the socialist writer E. Haldeman-Julius. Shoemaker made extensive notes in English and Spanish between the margins of particular favorites, from The Lies of Religious Literature to The Ghastly Purpose of the Parables and Volney’s Ruins of Empires.

Shoemaker focused on veteran’s issues, joining the American Legion in 1919, the same year it was founded. However, his concern for comrades-in-arms didn’t equate a militaristic mentality. During the mid 1920s, he dashed off the lines:

How cruel are most of man’s emotions,

How mad are many of his ways,

But the cruelest of all his silly notions is war.

Shoemaker began studying law and was admitted to the Iowa bar in 1923. He married, had four sons and a daughter, then lived in California for a time before moving to Portland. All the while his political consciousness developed, in 1926 writing: 

The poverty of the masses in all ages has been the direct and logical result of their slavery = chattel slavery, feudal slavery, wage slavery. [G]iven economic freedom, all men and women can earn and enjoy a good, secure living.” 

In another comment that year, he was even more direct, stating: 

Man must improve with the times, and the relationship of men to property must change = or the majority must get off the earth, because no food will be allowed them.

While other Americans adopted more drastic left or right-wing politics as the Great Depression spread during the 1930s, Shoemaker remained optimistic social change could occur within existing systems. Then, once the US entered World War Two in 1941, his anti-war ethics were tested. Shoemaker viewed American imperialism skeptically but saw German and Japanese fascism as greater threats to humanity. All of his sons enlisted in the armed forces and, by now too old for combat duty himself, Shoemaker served overseas as a Chief Yeoman with the famed Navy construction battalion, the Seabees. 

After the war, Shoemaker took up practicing law once more and by 1951, became notable enough that when a circuit court position opened, Oregon’s governor appointed him. This awarded rare institutional power to a true believer from the old Free Thinker movement. Still, what difference could one judge make? Besides that, Portland’s police department was notorious for right-wing connections, after openly deputizing Klansmen in the 1920s to unofficial “Red Squads” who monitored domestic political activity. Even its first union president in 1942 was a longtime member of the German-American Bund, a Nazi party offshoot who marched with swastika banners and fought anti-fascists in the streets. 

Portland also held a reputation for organized crime activity in those years. FBI investigations and even a US Senate Committee probe five years later revealed corruption spreading deeply from the top down. Illegal gambling halls operated semi-openly, with payoffs to beat cops who looked the other way. Any reasonably savvy official in the criminal justice system understood this and Shoemaker was no fool. In 1952 he penned a frustrated editorial titled: “Judges Under Wraps” declaring: 

It seems absurd that a judge who holds his position because of his fairness, impartiality and integrity should thus be compelled to sit as a helpless referee, unable to express an opinion or judgment upon fallacious arguments, palpably false stories, or in any way to guide the investigation or help the jury to ascertain and determine the truth. 

If anything defined Shoemaker’s early years on the bench, it was great kindness. Local media reported about how on April 22, 1952, he relocated his entire court proceedings to the living room of a housebound woman and later that year showed mercy on a man whose truck operator’s permit was revoked because of epilepsy. Many times he threw out cases against minors possessing alcohol or situations involving expired licenses. Other judges took a harder line with offenders, from levying hefty fines and long sentences to requiring “greasers” shave their distinctive haircuts before appearing in court. When Shoemaker saw crimes as victimless, he typically reduced or waived financial penalties and prison time. 

For Judge Shoemaker, by then divorced, his personal life took a major turn on July 3, 1952 when he married again, this time to Frances Bertram Hine, a woman thirty-one years his junior. Preferring the name Billie, she came from an East coast family and worked as a Spanish teacher and swimming instructor. Their relationship was quite tender, and many intimate letters between them survived. A great purveyor of nicknames, she dubbed him “Fuzzy” and Shoemaker in turn addressed letters to her as querida, Spanish for dearie. Over the years, media accounts treated their bilingualism as a great novelty. On one occasion where the judge conducted a wedding in Spanish, Shoemaker seemed bemused at the sensation this caused, making an apology that his Arabic and Thai were terribly rusty.

Interestingly enough, Billie’s father, Henry Francis Hine, was a prominent clergyman from the Anglican church who delivered a public address in 1940 labeling atheism “the real Fifth Column” before claiming “The only reason our country is still free from enslavement is the church…” It presumably caused quite a shock discovering his new son-in-law was an atheist. Despite this glaring difference, the two men developed quite a warm friendship, attested throughout personal notes and family photographs.

Over the next several years, Judge Shoemaker grew less wary of controversy. In September of 1956 he infuriated the Oregon Temperance League after returning alcohol to an underage married man, explaining to news outlets, “It is my opinion… that any man with a family and a job who is supporting his family, doesn’t come within the spirit of the law prohibiting minors under 21 from having liquor in their possession.”

That same month police officers raided an establishment connected with gambling in North Portland. The four arrested men were Black and given well known corruption in that industry, it wasn’t surprising initial evidence connected two white city officials, who denied involvement and were apparently not investigated further. This bust drew much sensational press coverage so it made quite a splash when Shoemaker released the men with only minor fines and even returned cash that police seized, but never connected with illegal activity. One irate local minister even delivered a sermon fiercely condemning the judge.

In Shoemaker’s next published letter, during September of 1957, he called white crowds protesting Black children attending an integrated school during the Little Rock Nine affair “beasts.” His anger came across so strongly that a reporter pressed him some days later, apparently seeking a more conciliatory spin. Shoemaker responded with a personal example, citing one recent case where an all white jury found two Black defendants innocent, despite the aggrieved party being a “good-looking, well-dressed white woman…” 

Also in 1957, Shoemaker revisited a favorite subject, advocating more understanding for young people, pointing out in an editorial: “I have heard many respectable adults brag a little about their own youthful exploits beyond the law” He urged less public funds be spent incarcerating minors and instead direct resources toward improving schools and better mental health treatment for “disturbed” individuals. By now, it was apparent the judge posed a regional political influence. Newspapers reported Shoemaker’s opinions on most any matter and even kept readers regularly informed about construction progress of a swimming pool at his house. 

More importantly, 1957 was the year of accountability for many prominent officials involved with organized crime, including the police chief, indicted for “incompetence, delinquency and malfeasance in office.” So Portland’s Free Thinking judge grew even bolder. In April of 1958 he wrote an article condemning fascism, as recent surveys indicated many Americans believed “some super-authority should decide what is best for the people. . . that freedom of the press should be abolished. . . . [and] that some people should be denied free speech.” He particularly warned against increasing police powers to search individuals and advocated a more communal mindset among youths “whose duty it is to preserve the freedom we can so easily lose.”

An example of the policing powers Shoemaker feared soon arrived. Around late March of 1959, a radio personality named Alfred Alexander spied an intoxicated man prowling near his neighbors’ house. He confronted this individual who reacted belligerently. The encounter turned violent, with both men trading blows until the interloper revealed himself as Officer Wade Chatfield before placing Alexander under arrest for assault. The station deputy who booked Alexander reported Chatfield had been drinking, was off duty, and wearing plainclothes while apparently earning extra cash as a process server which explained his snooping.

Shoemaker summarily dismissed all charges against Alexander. The radio host then filed a lawsuit of false arrest, which also named Multnomah County Sheriff Francis Lambert. Unfortunately for Alexander, a less sympathetic judge deemed his complaint groundless and Chatfield received no further known consequences, though Lambert eventually forbade his deputies from “moonlighting.”

The police saw Shoemaker’s intervention against one of their own as a declaration of war. Sheriff Lambert certainly felt threatened, yet hesitated before taking action personally. Officer Chatfield’s drunken escapade made law enforcement look bad and further scrutiny might increase demands for civilian oversight. So Lambert waited until a better excuse came along. Street level cops, however, were far less cautious. They launched an unofficial strike against Judge Shoemaker beginning May 1st which almost immediately dropped his traffic offense caseload by 75%.

Then, after turning a blind eye or possibly encouraging their conduct for several weeks, Sheriff Lambert announced a formal police boycott on Shoemaker’s court on May 28, 1959, which he termed too “lenient,” declaring “all traffic and misdemeanor arrests” would be rerouted to Gresham. When questioned for specifics, Lambert claimed two of his officers were poorly treated when they visited Shoemaker to dispute his handling of a “motorist charged with reckless driving and resisting arrest.”

Shoemaker acknowledged the encounter and pointed out “it is the job of deputies to arrest a man, and not judge the case in court.” The judge sharply added he considered attempting “to discuss a case after it has been disposed of” to be “contempt of court.” He declared Lambert’s boycott unconstitutional, pointing out: “The law requires that the arrested person be taken to the closest and most convenient magistrate.”

Officers began making anonymous complaints about Shoemaker, echoing Lambert’s criticism and adding: “He makes a fool out of you in court and makes accusations against you so that it seems you’re the one on trial instead of the accused person.” Shoemaker fired back, stating: “A judge has a duty to stand between the public and some of these deputies who want to make a police state out of this country.” Amidst all this, one State Representative stepped forward in support, claiming Lambert’s actions “smacked of [an] attempt to intimidate the judge.” 

News reports claimed officers who supported this boycott were “in the majority.” Still, it’s unclear how Lambert expected a police mutiny would play out long term and his resolve quickly faltered. Within twenty-four hours, Lambert called off the boycott following a “peace parley” arranged by the local district attorney. It concluded in victory for Judge Shoemaker who denied any wrongdoing and made no promise to run his court more harshly. When questioned, Sheriff Lambert “declined comment on the settlement.”

Their feud ignited again in October 1960 after officers chased a man for speeding who became verbally abusive once pulled over. They towed his vehicle, which was apparently not typical. When Shoemaker heard the case, he bristled, interpreting this as petty abuse of authority and struck the impound fee off a $25 traffic fine (around $222 today). The cops argued, with predictable results from Shoemaker, so they next brought their complaint to Sheriff Lambert.

Lambert assailed Shoemaker publicly, this time threatening to file an affidavit of prejudice, adding that he wanted “to get along . . . . but it is apparent that the public interest is not being served.” Shoemaker responded, framing the incident as an unjust confiscation of private property, saying officers did not have “the right to tow the car just because the man gave them a little lip.” He wondered why Lambert lacked enough “grace” to simply discuss their disagreements before “issuing press releases” because“it is up to the courts to protect the rights of individuals and the sheriff is not going to tell me how to run my court.” Once more, Lambert backed down, earning the sensational newspaper headline: “Sheriff Drops Plans to Attack Judge Here.” In 1962 he chose against seeking election again.

Judge Shoemaker continued conducting court as he saw fit and in 1964 was reelected with a popular landslide. Then, life took an unusual twist. Around the mid-1960s, his wife Billie began an affair with Dr. Babette Ellsworth, a prominent university professor. In those days Ellsworth was known for regional geology and history expertise but later gained fame as a transgender pioneer. The two carried on a romantic relationship, eventually gaining Shoemaker’s knowledge and consent. By 1969 the judge retired and in 1971, Dr. Ellsworth moved into his and Billie’s home. 

Years later Ellsworth recounted how this dynamic unfolded: “Shoemaker took me into his office privately. He explained his wife loved me and as a wilful individual, would certainly leave him if forbidden to see me… He feared solitude and proposed a solution. I could reside in his house and we would all make the best of things.”

Over the next several years Dr. Ellsworth and Billie took care of the former judge as his health declined. It’s unclear how their relationship avoided scandal, as in times past, even Shoemaker family Thanksgiving plans made the papers. This shift was simply mentioned without comment, as seen in a 1973 article where Dr. Ellsworth and Billie were photographed grinning widely as they pedaled together down a country road. A reporter noted the pair “ride their old bicycles together on Sauvie Island most weekends.”

In 1974 all three took a road trip through Montana, stopping in Glasgow where local media honored Shoemaker’s return with some fanfare. He toured the town, pointing out changes in scenery and reminiscing about the old days. Then on April 30, 1977, Ray Shoemaker went for an afternoon walk around their neighborhood and immediately suffered a fatal heart attack upon returning home. One of the last Free Thinkers would never again infuriate Portland’s police department or dispense courtroom mercy to those in need. A man who told the newspapers upon retirement: “I’ve always felt a just judge has to have a kind and understanding heart.”

In retrospect, it’s worth examining how he got away with everything. After all, Shoemaker was a former Colorado miner whose fellow workers were machine-gunned by private militias and the US military some few hundred miles away during the Ludlow Massacre of 1914. He was a leftist who made powerful enemies among law enforcement during the “Red Scare” when many other careers were destroyed over hints of so-called “Un-American activities.” The answer draws largely from deep reservoirs of goodwill he spent decades cultivating and deep roots in respectable civic groups. 

Shoemaker was a devoted member of many fraternal organizations, particularly those with patriotic appeal, from various Masonic groups to the Elks and Eagles. He regularly performed community services, such as visiting high school classrooms to explain the criminal justice system and participating in free legal forums. Simply declaring police officers should operate by the same accountability standards as everyone else and running for election as a “sympathetic, just, [and] understanding” candidate won him great popularity.

Despite his wife’s lover, Dr. Ellsworth, being the subject of various FBI investigations from 1950 until at least 1978, a Freedom of Information Act request indicated no such file existed on Shoemaker. It’s difficult imagining no attempt occurred, given his high profile controversies. In the case of Ellsworth, agents extensively questioned her friends, colleagues and neighbors for information about potentially subversive political views. Though a notable academic figure, Dr. Ellsworth counted on few friends in high places, spoke with a thick French accent, and struck many people as odd, even if her transgender status remained unknown.

By contrast, the judge boasted numerous influential allies, besides serving as a longtime American Legion commander. If suspicious officials ever visited his Montavilla Post #163 to pose insinuating questions, they likely found an unreceptive, if not hostile audience. Shoemaker also avoided making systemic criticisms. Even many of his most incendiary comments were phrased in calculated ways. It’s important to recognize that as an American who came of age when consequences for unpopular political speech might be prison or worse, he recognized limits and carefully avoided crossing them.

This may seem like naked self interest…after all, Shoemaker lived a long life, surrounded by comfort in his later years and the companionship of an unorthodox love triangle. Yet at least for those who experienced justice in his court, this judge made a difference, one that still resonates whenever Portlanders stand up for police accountability and insist all citizens be treated equally under the law.

All citations, references and quotes not from Ray Shoemaker’s personal papers or my own book Babette: The Many Lives, Two Deaths and Double Kidnapping of Dr. Ellsworth are from the The Portland Journal, The Oregonian and The Star newspapers.