The Hollywood version of her story.

Before dawn, Phillips scrawled those details in a note, which she slipped to a Filipino runner in the alley behind the club. The runner vanished into the mountains to rendezvous with Boone’s guerrillas. A shortwave transmission relayed news to General Douglas MacArthur in Australia or New Guinea. And then, often enough, the Tsubaki Club’s guests met unpleasant fates. Phillips later claimed that one of her tips led to the annihilation of an entire Japanese submarine squadron.

Meanwhile, Phillips spent her days—and her club’s profits—on another mission: smuggling food, notes, and medicine to American POWs held at the Cabanatuan prison camp outside Manila. For these men—sick, starving, prone to maltreatment and random execution—she was both a practical and emotional tether to the world. One imprisoned soldier wrote to Phillips: “You’ve done more for the boys’ morale in here than you’ll ever know … You deserve more gold medals than all of us.”

For her part, Phillips always signed her dispatches: “Yours in war, High Pockets.”

Eventually, the Japanese caught Phillips. Interrogators shot water into her mouth from a hose. “Guards held my head so that I could not move,” she wrote. “I held my breath. A Nip noticed this and hit me in the abdomen. I gulped the water down … drowning on dry land … then oblivion.” Captors burned her skin with cigars until she awakened. By the time American troops liberated her prison on February 10, 1945, she had lost 55 pounds.

On a rainy Tuesday in 2010, Sig Unander walked up to a green-gray midcentury cottage with chipping paint and a crop of weeds, just east of Murray Boulevard in Beaverton.

No one answered the doorbell. This had been Phillips’s postwar home, a reward for her Manila service. Today the place feels more like a monument to oblivion than heroism.

After the war, High Pockets seemed to rebound well. First came a Reader’s Digest feature. Then, at MacArthur’s recommendation, a Medal of Freedom—the nation’s highest civilian honor. Her published memoir led to the movie. (Phillips was arguably prettier than Dvorak, but the casting was apt: Dvorak has been called “Hollywood’s forgotten rebel.”) Phillips went to Hollywood to advise the production and hobnob with stars like Dvorak, whom she’d helped choose as her cinematic double.

Soon after, Phillips was guest of honor on NBC’s top-rated radio show This Is Your Life. Back in Portland, more down-home honors flowed. A Beaverton developer provided the house. A local Packard dealership gave her a new car. Lewis & Clark College pled-ged free tuition for Dian. Hundreds gathered before a makeshift stage in the driveway to watch the lady spy take the keys to her new home.

But her life descended quickly. Working at Lipman’s department store wasn’t her idea of adventure. Within three years she divorced a third husband. Dian dropped out of high school, never accepting the scholarship. In the late ’50s, Phillips also faced a public comeuppance when she unsuccessfully sued the US government for $146,850 in compensation. Support came from Boone and Oregon Senator Wayne Morse, but she was rigorously cross-examined and chastised for her inability to document what she spent in Manila. “Much of her story was greatly exaggerated and at times almost fanciful,” the US Claims Court decision read. Phillips received just $1,349, even though others with little documentation received large sums.


The Hollywood version of her story cast Ann Dvorak as the sassy Franklin High graduate.

Phillips often woke up screaming at night. She drank. She’d die within a decade of meningitis. “She never was very well after she got home and never very happy,” her mother wrote to a relative afterward.

In recent decades America has celebrated the “Greatest Generation,” perhaps at the expense of the individuality—in some cases, the essential strangeness—of its members. Claire Phillips’s wartime intrigue and lost love are ripe for rediscovery. A signed copy of her book currently fetches up to $200 on Amazon, and one can almost imagine Angelina Jolie or Cate Blanchett fighting over the role. Yet Phillips is most compelling not as a faultless hero but as a human beset by imperfections: the sultry singer with the meteoric fate, the loose cannon who met her historical moment, then watched it slip away.

“This woman relished the lime-light, loved to take chances, and was an adventurer,” Unander said as he departed the rain-soaked old Beaverton house. “She’s not going to be happy playing mahjong with the girls on a Wednesday evening. One of her relatives said that Claire never slept with the lights off. She’d lived a dozen lifetimes in a few years.”