How Japan Lost World War II: An American Spy's Story of Seduction and Intrigue

On December 7, 1941, hours after Japan's surprise assault on the U.S. naval base at Pearl Harbor, Tokyo's Imperial air force also attacked the Philippines, bombing Manila and other cities.

Claire Phillips, a singer from Portland, Oregon, was trapped in the Philippine capital when the attack began. Within days, she fled to the hills of Bataan, where she tended to the sick and wounded. There, she encountered American and Filipino guerrilla fighters who had escaped after being ordered to surrender to the Japanese army in April 1942. Eventually, an American rebel commander asked her to return to Manila to send supplies. Despite the obvious danger, she agreed.

With help from friends, Phillips started running Tsubaki Club, which soon became the hottest nightspot in Manila for Japanese officers, who knew her only as Madame Tsubaki, a Filipina saloon owner. In reality, she was something else—an American spy.

Karma Camellia

On January 1, 1943, Phillips sashayed onto the nightclub floor—the spotlight casting her curvaceous silhouette against the creamy drapes—and began to sing:

I don't want to set the world on fire
I just want to start a flame in your heart

For two months now, Phillips—the tanned, dark-haired proprietor, hostess and featured performer—had ensorcelled the patrons here, mostly Japanese officers and businessmen, along with the Filipinos who did their bidding. As she sang, Phillips looked around with satisfaction. The club was so packed, they had to turn people away. Many spoke English. But for those who didn't, her sultry gaze and husky voice were more than enough to convey the song's message.

Everyone wanted to see the floor show at the Tsubaki (the name meant "camellia," a rare, delicate flower in Japan). The club was at a busy intersection near a romantic downtown park where palms and acacia leaves rustled in the breeze from Manila Bay, softening the heat that regularly stifled the city during the day. Streetlights cast shadows at the entrance of the club, a two-​story wooden house set back from San Juan Avenue.

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At the start of the evening, Phillips had greeted guests at the head of the long, winding staircase. As they climbed to the second floor, they looked up to see her. The slit in her long, elegant gown made an alluring line from her ankle to the lower part of one thigh, an intoxicating peek into another world. Phillips then led them to one of the more than a dozen small tables around the room or to rattan chairs on the periphery, where they could lounge and drink and watch the show.

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The U.S. Embassy in Manila, Philippines, named a meeting room for Claire Phillips, where it displays an oil painting of her as a young woman. U.S. Embassy, Manila

The floor show at Tsubaki Club was a big draw. When it was Phillips's turn to sing, they all moved close enough to breathe in her scent and admire her curves. She sang a set of American standards, the songs popular back home right before war broke out and just as popular among the Japanese men.

Many were smitten—not only with her, but with the alluring young women she had trained to act like geishas: sitting and flirting with the soldiers, lighting their cigarettes and pumping the lonely, homesick men full of drinks, before asking them questions. Darling, the dew-​eyed women might say to their Japanese guests. Why must you leave so soon? Where are they sending you? Can I write to you? When will you come back to me?

There was a secret life surrounding Tsubaki Club that Phillips did not mention. Of course, the young women, many of them teenagers, were out to charm the Japanese officers and the civilians who came to spend their money at the club. Sometimes, a night of charms could become something more. Everyone knew there were plenty of brothels in Manila for men who were interested only in sex. Phillips had tried to brand her club as something different, something more "sophisticated" and "high class." But Tsubaki Club did not prohibit women from recruiting inside before taking their business outside. There were plenty of hotel rooms close by.

At the end of the evening, Phillips would retire to her dressing room, take off her gown and wipe off her makeup. Some nights, she had to fight the men away from her door. But she couldn't tarry. She had to return home before curfew, or risk being stopped by a Japanese soldier who might slap her around for breaking the rules.

The next morning, she would have breakfast and go back to the club, where she would gather reports from all her women, hostesses and performers. They collated the names of the Japanese military men and their units, and, if they were lucky, where their ships were headed. Several times a week, a runner from the hills or one of the men who worked as waiters could hide the report in the fake sole of a shoe or in the lining of a shopping basket, then carry the latest intelligence to his American or Filipino guerrilla contacts in Bataan.

Once that information was collated and secreted away, Phillips would prepare for that evening's performance, ready once again to set the world ablaze.

'Here's to Killing Many More Americans!'

Phillips had opened the club in October 1942, and it quickly became packed. She even offered personal attention to high-profile guests.

One night, in late 1942, she sat with a Japanese army pilot, recognizing that he was important enough for special treatment. The night passed quickly: drinks and more drinks, tips for the geishas and then the floor show. Phillips sang one of her standards; sometimes, it was something by the well-liked American quartet the Ink Spots, or perhaps "Some of These Days," a popular tune back in the States. "My rendition did not equal that of the inimitable Sophie Tucker," she recalled in her memoir after the war, "but it served its purpose."

The drinks and entertainment had the desired effect. The drunk pilot boasted in broken English. "The U.S. didn't stand a chance," he said. "Many Americans would die."

As the night wore on, he kept bragging about the coming wave of casualties. Dozens of dead Americans. "Banzai!" the pilot shouted and raised his glass. Phillips toasted with him and took another drink. Hundreds of dead Americans. All the officers raised a glass to that. And here's to killing many more Americans in the future. "Banzai!"

Phillips raised her glass once more. "Had to drink to the death of more and smile," she confided to her diary that night. "Not easy."

Phillips toured the United States in 1951 to publicize a film based on her life, "I Was a American Spy." American International Pictures

The bar's staff watched with amazement at how she sweet-​talked the Japanese officer. The "employees think I'm crazy," she wrote in that diary. "Don't understand when I drink to downfall of England and America with finger crossed."

While she toasted the death of many Americans with the pilot, she followed the same instructions she gave her staff. She gathered tidbits of information from him: his plane, his unit, anything that could help defeat him and the Japanese war machine.

Sometimes, however, such conversations with the Japanese military men were too hard to take; Phillips would excuse herself, rush to the bathroom and vomit. Then, she would return, smiling once more, ready for another drink.


Sleeping With the Enemy

Most Filipinos were repulsed by the occupying Japanese army and refused to consort with them. Women who had taken up with Japanese officers lived in fancy hotels but were reviled for it. It was also dangerous—some women had been killed for siding with the enemy.

Phillips hated the Japanese, but she had to play her part. As a result, Filipinos sometimes shunned her on the street. At times, she fretted and thought about closing the club. She was drinking too much, smoking too much and constantly tense. Part of her stress: Aside from being a spy and nightclub owner, she was also a mother to Dian, the 3-year-old girl who had been her foster daughter since infancy. Phillips's only refuge was a stolen moment scribbling a few lines in her little date book. "Fear for my sanity, really. My book is a comfort. Can let my hair down to it and it alone."

Japanese officers came and went, and some wanted more than a dance. Once, she got word that a colonel who swore he was in love with her had died in battle. She hoped it was because of information she had sent up to the guerrilla contacts in the hills.

Phillips hated herself when she occasionally took pity on one of the Japanese. They were young, and some were kind to her, or they confessed they missed their families and just wanted to go home. Yet war was war: She gathered each name of every officer and sent it to the hills. Most of the men made it easy for the women to hate them, especially when the men got drunk late at night and beat them with their bare hands, or sometimes with whips or scabbards. Filipinos were subject to petty brutalities without recourse. It was obvious that Japanese officers were not honoring orders from Colonel Nagahama, the chief of the Japanese military police, that they treat people courteously and avoid the habit of slapping them in the face for not bowing deeply or quickly enough or for being slow to follow orders. It was a constant indignity and sometimes worse. "I don't know how long I can take this face-slapping," Phillips wrote. "Twice tonight." She also wrote that someone also had hit her with a rubber hose—she didn't say where or how it happened. "Leg better today. But still swollen. God how I hate them."

Her early months of success in collecting information and earning money at the club brought constant tension, the abiding fear that she could be caught and killed. Phillips converted her anger and hatred into a compulsion to stay busy, gathering secret shipments of food and medicine for the guerrillas and for prisoners of war, writing reports during the day, operating the club and gathering bits of information at night. By the fall of 1943, Manila was running out of food and supplies. The goal was to send more support than ever before, even when prices were going up and beer was sometimes hard to buy. Without enough beer and other alcohol, business and receipts were certain to drop. To save money, she was forced to give up her apartment at the Dakota, a five-minute walk away, and to move into the club. At least she wouldn't have to worry about the racing home in time for curfew.

By the end of 1943, grocery stores no longer sold sugar, flour, beef, or even fruits and vegetables. Rationing was imposed to provide basics, and people were forced to turn more and more to black marketeers who gouged them.

Phillips cut back on her budget even more, avoiding expensive food and diversions such as movies and books and eating out. "Only bare necessities now," she wrote in her diary. "Everything stay[s] high. Hard to make both ends meet."

Despite the pressure, Phillips kept fighting. She was saving lives. And the pressure and fakery surrounding her life were helping the country win the war. Soon, she hoped, it would all be over. And General Douglas MacArthur would fulfill the promise he had made to the Philippines when he fled in 1942 to regroup: "I shall return."

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Peter Eisner is a journalist and author. This story is adapted from his newly released book, MacArthur's Spies: The Soldier, the Singer and the Spymaster Who Defied the Japanese in World War II.