Offbeat Oregon History

Portland woman ran American spy ring in occupied Manila


September 14, 2023 | View PDF

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, an 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.

“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.

Finn J.D. John teaches at Oregon State University and writes about odd tidbits of Oregon history. His book, Heroes and Rascals of Old Oregon was recently published by Ouragan House Publishers. To contact him or suggest a topic: [email protected] or 541-357-2222.

Continued Next Week


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