Portland woman ran U.S. spy ring in World War II

By Finn J.D. John
September 1, 2023

SOMETIME IN 1943, during the Japanese occupation of the Philippines, a group of more than 40 officers of the Imperial Japanese Navy strolled into Club Tsubaki, an exclusive gentlemen’s club in the heart of downtown Manila.

They were there for one last evening of fun while they were still in port. That very evening, they were scheduled to climb back into their submarines and set out on an extended cruise.

The private party had been arranged by one of the subs’ commanders, who had struck up a friendship with the owner of Club Tsubaki, a gorgeous Italian-Filipina dancer named Dorothy Fuentes, a.k.a. Madame Tsubaki.

For hours, as Madame Tsubaki and her sultry staff danced and sang for the officers, the men had the time of their lives. The floor show was magnificent, the women were alluring, and the alcohol was flowing freely.

And, after a few more drinks, so were the details: The flotilla of subs was on its way to the Solomon Islands and would be leaving the next morning.

Finally, happily exhausted and still pretty drunk, the group of officers staggered off to their boats at 6:30 a.m., and Madame Tsubaki’s dancers finally got to go to bed.

At about the same time, across the bay, a young man named Pacio was hurrying up into the hills, making for a rendezvous with a small band of American and Filipino Army guerillas. The guerillas, under the command of a firm-faced American corporal named John Boone, had a radio set.

The race was on to get the word out to Gen. Douglas MacArthur in time to arrange an ambush for the flotilla of submarines as they motored out of the harbor.

Pacio had a good head start — he’d had the info he needed much earlier in the evening. It had been handed to him at the back door of the kitchen by Madame Tsubaki herself.

If the officers had had any inkling who Madame Tsubaki really was, they would have been horrified. By 1943 every Japanese officer in Manila knew about the shadowy underground figure known only as “High Pockets,” a sort of Manila master spy running a secretive network of guerillas and couriers throughout Manila, funneling supplies to the guerillas and smuggling food to the starving prisoners of war in their internment camps.

High Pockets, in turn, was the nom de guerre of Claire Phillips, a gorgeous brunette Vaudeville girl from the faraway American town of Portland, Oregon … a dancer of sultry dances, a singer of torchy cabaret songs, and a stage actress of unusual ability.

In the Philippines, in the early years of the Second World War, she was playing the role of a lifetime: Madame Tsubaki, Italian nightclub owner.

(“High Pockets,” by the way, was a coy reference to Claire’s habit of hiding secret messages in her brassiere.)

CLAIRE PHILLIPS WAS born in Wisconsin, but moved with her family to Portland very early; her maiden name was Snyder. As she grew up she turned out to be something of a hellion.

After her freshman year of high school at Franklin High, Claire ran away from home to join a circus. It took her mother, a pious Christian Scientist, four months to track her down, but she did, and dragged her back home; but then, apparently hoping to keep history from repeating itself, she helped the girl get a job with Mayor George L. Baker’s wholesome and respectable stock theatre troupe, Baker’s Players. This was in the early 1920s.

Claire took to the stage like a true natural. Soon she was traveling with Baker’s troupe.

By the late 1930s, she was in Manila, singing torchy love songs in cabarets and having a great time. She had met and married a Filipino man named Manuel Fuentes. The match didn’t take; they divorced soon after. But Claire got a daughter out of the deal, a little girl named Dian.

Just before the war broke out, she met the man she always considered the true love of her life — Sgt. John “Phil” Phillips of the 31st Infantry Regiment.

When the Japanese invaded, Phil was taken prisoner, and he subsequently died of malaria and malnutrition in Japanese custody.

After the invasion, from a hideout on a rocky outcropping, Claire witnessed part of the Bataan Death March, on which American and Filipino soldiers were forced to walk about 65 miles to their new prison camp. Along the way, soldiers who fell out of line for any reason (dropping from exhaustion, going for a drink of water from a nearby ditch, etc.) were ruthlessly bayoneted and left writhing and dying in the dust as the column trudged on. Claire watched all this in mounting horror.

Then Cpl. Boone — a friend of Phil’s, from his old unit — approached her. He and some of the uncaptured soldiers, he said, were taking to the hills, Robin Hood style. If she could arrange to stay in Manila, and maybe help keep the guerillas supplied ….

By this time Claire knew Phil had died, so it was now personal. Yes, she told him. Count on me.

And for about two years, he did.

OF COURSE, IT couldn’t last forever. In May of 1944, one of her messengers was caught slipping food and supplies to POWs at one of the notorious prison camps. Under torture, the messenger gave her up … and on May 23, the Japanese military police came to Club Tsubaki and roughly arrested her.

Claire was interrogated, tortured, waterboarded, and burned with cigars. She played her cards carefully, spilling stale information (naming people who she knew had already left the area or been arrested or killed) and acting as if she was betraying trusts in doing so. It also helped that the only thing they knew about at the time was her smuggling of food and supplies to POWs and other prisoners. Had they known she was passing on military intelligence as well, it probably would have gone even worse for her.

Tried in a military court, Claire was sentenced to be executed. This was subsequently commuted to a sentence of 12 years at hard labor.

Less than a year later, the American forces liberated her prison. They got to her just in time — she had wasted away to under 85 pounds (her healthy weight was about 140) and had to be fed intravenously at first because her digestive system had shut down.

AFTER THE WAR, Claire was hailed as a hero. Even before she was back in North America, her hometown newspaper was singing her praises. Soon afterward, Reader’s Digest picked up the story and spread it nationwide.

She wrote a memoir of her war activities, Manila Espionage, and it was published in 1947. The following year, at Fort Lewis, Gen. Mark Clark presented her with the Medal of Freedom, America’s highest award for a civilian.

The accolades kept coming. She appeared on an episode of NBC’s This Is Your Life, with the legendary Ralph Edwards. Afterward, she was presented with a home in Beaverton and a new Packard automobile. She threw herself into the lecture circuit, giving speaking engagements and appearances around the country talking about her time as an American spy behind enemy lines.

She even had a Hollywood movie made about her, starring Anne Dvorak, in 1951. It was called I Was an American Spy.

But behind all the activity, all was not well with her. Always a restless spirit, she’d been deeply traumatized by the cruelty she’d witnessed and the torture she’d experienced. Post-traumatic stress disorder was not yet a known thing, but oh yes, she certainly had it. Nightmares woke her up screaming in the early morning hours; she beat them down with a bottle, drinking enough alcohol to ensure deep enough sleep to not be disturbed by her inner demons. Soon she was a certifiable alcoholic as well as a workaholic, and predictably, her health began to deteriorate.

THEN, NEARLY AS quickly as she’d risen to fame, the world seemed to make a special effort to forget her.

Her mistake, the one that precipitated her fall from public grace, was an understandable one: She put in a claim for compensation from the government, for the expenses she’d put up during the war, and got a little carried away with her figures.

After all, how does one put a dollar value on a trauma like the one she experienced?

Most likely the way she set about it was to tally up all the revenue she received from Club Tsubaki, which she spent as quickly as she got it on relief supplies for the guerillas and prisoners, and add a healthy percentage for interest and incidentals.

In any case, the figure she came up with was $146,850 — which, in modern currency, would be worth about $1.6 million. This was such an enormous figure that it caused many people who would probably have been favorable to her case to turn away, dismissing her as a gold-digger.

Naturally, her documentation was scant. The federal employees and FBI agents processing her claim suspected she was trying to take advantage of government largesse, and they were not shy about expressing that view.

“She’s a prostitute,” one FBI agent wrote, in a note he left in her file. “Got a lot of publicity and is a phony.”

She also had a falling-out with some of her wartime colleagues in the Philippine resistance, and at least one of them started spreading rumors that she had been a Japanese collaborator. As Madame Tsubaki, her job had been to vamp Japanese officers; so naturally many Filipinos at the time hated her for consorting with the hated occupiers, and accused her of being a Japanese collaborator. Not all of these rumors were extinguished by her arrest; plenty of real collaborators got arrested and jailed by the Japanese during their occupation.

In the end, the government took the position that she was entitled to nothing, and the judge awarded her $1,349.21, which probably didn’t go far beyond covering her attorney’s fees.

That was in 1957. Three years later, weakened and getting sickly, the 52-year-old war hero caught meningitis and died.

FAME AND ADULATION are fickle things to begin with, and they seem to be especially fickle for women. In any case, following that initial postwar burst of enthusiasm for her wartime service, Claire Phillips fell quickly into obscurity. Following her death, she seemed utterly forgotten-about. Documentarian and author Sig Unander deserves a lot of the credit for bringing her story back to life. Unander has been working on a full biography of High Pockets for several years now, and when he finishes it it will probably become the definitive work on this fascinating Vaudevillean war hero.

Most recently, in 2017, the Oregon State Capitol Foundation unveiled the Claire Phillips Memorial, on the northwest corner of the state capitol grounds in Salem, at a ribbon-cutting ceremony with Gov. Kate Brown.

“Claire Phillips,” the governor remarked, “follows in this Oregon tradition of women who truly fly on their own wings.”

And how.

By the way, in case you’re wondering, no one is 100 percent sure what happened with the flotilla of submarines that Claire sent away to its doom after the all-night party with its officers. In her book, though, Claire writes that she heard back from one of them later, and he told her he was the only survivor.

(Sources: “Claire Phillips: Forgotten Hero,” an article by Sig Unander published in the January 2016 issue of 1859: Oregon’s Magazine; “Claire Maybelle Phillips,” an article by Sig Unander published May 11, 2022, in The Oregon Encyclopedia; “Manila Mata Hari,” an article by Brian Libby published in the February 2011 issue of Portland Monthly magazine; Manila Espionage, a book by Claire Phillips and Myron Goldsmith published in 1947 by Binford & Mort; "Portland Singer Claire Phillips became a spy ...," an article by Douglas Perry published Oct. 11, 2021, in the Portland Oregonian)

TAGS: #ClubTsubaki #HighPockets #ClaireSnyderPhillips #DorothyFuentes #ImperialJapan #WW2 #Submarines #Pacio #JohnBoone #USArmy #Philippines #DouglasMacArthur #ChristianScientists #MayorGeorgeBaker #BakersPlayers #StockTheater #ManuelFuentes #DianPhillips #SgtJohnPhillips #BataanDeathMarch #ReadersDigest #ThisIsYourLife #RalphEdwards #ManilaEspionage #AnnDvorak #FBI #BrianLibby #MyronGoldsmith