The real story behind Miss Moneypenny

The hundreds of women in British intelligence were agents, honey traps, code-breakers and—like the long-standing, formidable personal assistant to the chiefs of MI6 who inspired the Miss Moneypenny character—guardians of powerful secrets. Yet their stories have been buried like their classified files, their names absent from history and obscured by layers of secrecy and stereotype.

Historian Claire Hubbard-Hall spent countless hours combing through declassified archives, tracking down family members, and uncovering hidden private papers to uncover the truth about their vital work in her new book, Her Secret Service: The Forgotten Women of British Intelligence.

It was no easy task. Many carried their secrets to the grave, destroying crucial evidence in their final days. Others were so discreet that their own families were stunned to learn that “Great Aunt Ethel” had been a key figure in British intelligence—let alone working in the upper echelons of MI6.

George Wyndham: What inspired you to write this book? 

Claire Hubbard-Hall: A woman in intelligence, Stella Rimington [former Director-General of MI5]. In her memoir, Open Secrets, she was so honest about the challenges she’d faced as a woman on the rise of becoming the first female director general of MI5. But after I finished the book, I was left with many questions about the history of women in intelligence. For so long, it’s been men writing about men, which is understandable, because most of the people making the decisions were men. And these were people whose tradecraft was to avoid detection. 

GW: Aside from these women being so good at keeping secrets, why do you think their contributions to British Intelligence have been overlooked for so long?

CH-H: I think a big part of it is popular culture. The portrayals of the world of secret intelligence by authors like Ian Fleming and John Le Carré have heavily influenced public perception. And it’s very much a male-dominated world. 

The reality is that women were the engine driving the development of British intelligence, particularly its professionalisation over the years. Their contributions went far beyond what we see in most fictionalised accounts.

GW: Kathleen Pettigrew has been called ‘the real Miss Moneypenny.’ In your view, how similar was she to the fictional character?

CH-H: Any woman in intelligence who knew Ian Fleming seems to have been labeled “Moneypenny,” but Kathleen Pettigrew fits that title better than anyone. Fleming’s portrayal wasn’t entirely fictional—I’m certain the ever-present, all-knowing woman he wrote about was largely inspired by Pettigrew.

That said, they were very different. Moneypenny comes across as a polished debutante, someone from the “right circles.” Pettigrew, on the other hand, was a self-made professional from a working-class background. Her mother ran a shop to give her daughters a good education, and Kathleen’s success was built on skill and determination. She rose to become a Chief Executive Officer in Whitehall, a testament to how highly she was valued.

GW: Beyond their roles in the bureaucratic machinery of paperwork, how did women shape intelligence operations? I’m thinking of someone like Agnes Blake.

CH-H: Agnes Blake was the first woman employed as an MI6 agent in 1909 and is a great example of what real women in intelligence looked like. Unlike the glamorous depictions in spy films, women like Blake were chosen for their ability to blend in. The more unnoticeable they were, the better.

Looking at her photograph, she seems utterly ordinary—neither strikingly glamorous nor unattractive—which made her perfect for covert work. Hired as an “early warning” system, her job was to alert Britain if Germany planned an invasion or declared war. 

Thanks to her family’s connections to Kaiser Wilhelm and German military officers, she had access to valuable intelligence. She compiled detailed lists of officers and their roles, which were crucial to the Secret Service Bureau.

As a widow, Blake could travel freely between the UK and Germany without needing a chaperone—a rarity at the time, when unaccompanied women often raised eyebrows. She used her unassuming nature and freedom to move discreetly under the guise of visiting family. 

GW: What can you tell us about Winifred “Winnie” Spink?

CH-H: If I could host a historical dinner party, Winnie would absolutely have a seat at my table. She was independent, brave, brilliant, sharp, and adventurous, wearing a mini skirt at 17 and carving her own path. Her diary is extraordinary, not just for the personal insights but also for its links to major historical events—like the British intelligence involvement in Rasputin’s murder.

One entry stands out: the night Oswald Rayner, a British intelligence agent, lured Rasputin to the Yusupov Palace, where he was plied with drink, shot and dumped in the river. That same night, Winnie noted taking the mission car for a joyride around Petrograd with an unnamed driver. For someone so meticulous in her duties, it’s an odd detail, suggesting she may have been creating an alibi.

One of the most rewarding parts of this journey was finding and connecting with the families of these women. Many had little idea what their relatives had achieved. For instance, Winnie Spink’s family knew she’d worked in British intelligence but had no sense of the scale of her contributions. Dorothy Henslow, who spent a decade in MI6, was remembered only as working for an old Navy admiral.

GW: And Christine Chilver—codename “Agent Fifi”?

CH-H: Christine Chilver wanted to go behind enemy lines as an SOE [Special Operatives Executive] agent, but she was put to work on the home front testing trainee agents in a final exercise which lasted 96 hours. She would approach the trainees in a bar, restaurant—and even London Zoo—and see whether she could get them to reveal their true identity and mission details. 

For those who failed, Christine undoubtedly saved lives—that of the trainee and those behind enemy lines who would have been caught if the trainee had been sent overseas. Contrary to popular belief, Christine never slept with any of them. She was a consummate professional.

GW: Another interesting character was Olga Gray, AKA “Miss X”.

CH-H: Olga Gray was MI5’s greatest undercover agent. The secretary was given relatively little training by her spymaster, Maxwell Knight, and spent six years working under the cover of a secretary in the British Communist Party. Through her work, she uncovered the Woolwich Arsenal Spy Ring. However, during the trial, her true identity became known, and MI5 washed their hands of Olga without a thought for her care or that she may be of use training others for undercover work. She spent the rest of her life looking over her shoulder, wondering whether Russian intelligence would send someone to assassinate her.