Longreads

The Martha Stewarting of Powerful Women

Illustration by Jason Raish

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Ann Foster | Longreads | July 2019 | 14 minutes (3,613 words)

On March 5th, 2004, Martha Stewart was found guilty of obstructing justice and lying to investigators. At the time, she was one of comparatively few female CEOs, and she was irrevocably tied to her company’s success: her smiling, serene, WASPy perfection thoroughly entwined with her company’s numerous ventures. When she first faced charges of insider trading, news media and the general population reacted with schadenfreude, or as one New York Times article coined it, blondenfreude: the glee felt when a rich, powerful, and fair-haired business woman stumbles.” And stumble she did: In the wake of the scandal, Stewart voluntarily removed herself from most of her roles at the company, and as part of her sentencing she was barred from involvement with the empire for five years. Stewart re-joined the Board of Directors in 2011, but the company never truly bounced back from effects of the scandal.

The Times named Stewart’s conviction among the 20 most notable cases of insider trading, and she is both the only woman charged on the list, as well as the person whose alleged financial gains amounted to the least ($51,000), drastically less than the millions — and cumulative billions — of dollars taken by the men on the list, including Kenneth Lay, CEO of Enron. Samuel D. Waksal, founder of ImClone, the stock Stewart was alleged to have illegally sold shares from, pled guilty to orchestrating stock trades and was sentenced to seven years and three months in prison. Yet, it’s Stewart who would become the lead character in two made-for-TV movies — Waksal’s role in each is found much further down the call sheet.

There are countless other instances of men investigated for stock fraud at a similar level to Stewart’s alleged actions, and most of these men were not charged. Stewart was both investigated more ruthlessly than many of her male counterparts and she was also publicly shamed in a way men were never subjected to. In the end, the Department of Justice charges against Stewart for criminal securities fraud were thrown out, and a civil insider trading case the Securities Exchange Commission brought against her was settled. Crucially, neither of these alleged misdeeds were what ultimately landed her in prison. She was charged and found guilty of lying to investigators in an attempt to cover up her lack of insider trading: Yes, guilty for trying to cover up a crime she hadn’t committed in the first place. 

When news broke that she would face five months of jail time, it was greeted with delight by late-night TV show hosts, the news media, and seemingly most of the nation. Her case was covered more in the media than the concurrent investigation and trial of Lay by a vast margin, as coverage of Stewart dominated business, entertainment, home, lifestyle, and even some sports sections of newspapers. Between November 2003 and May 2004, the time period of Stewart’s trial and the Lay investigation, New York–based magazines featured Stewart in 1,507 articles; Lay, in just 12. Though Stewart was more of a celebrity than Lay, he had clear ties to then-President Bush and Vice President Cheney, as well as other high-ranking political officials. A scandal could have been made of his connections, but clearly that wasn’t as appealing to readers as minute-by-minute reporting on Stewart’s downfall.

Media coverage during Stewart’s investigation and trial was derisive, mocking the traditional feminine aspects of her empire as well as deriding her alleged “diva” behavior. This misogynistic treatment — both of her facing charges for lesser actions than men who never went to trial, and for the delight and nonstop news coverage of her trial and sentencing — would become the standard for treatment of formerly powerful women in the midst of a downfall. Let’s call it the Martha Stewarting of powerful women: a single-minded focus on their misdeeds, while countless men doing the same thing avoid the spotlight.

Martha Stewarting is hardly a new phenomenon, but the retrospective understanding of her treatment sets it in a new focus. Women as leaders have been rare throughout Western history, and those who strived to attain positions of power usually did so under designated survivor circumstances: There weren’t any male relatives left to take over the family property, the family land, or the kingdom. Nearly 1,000 years before Stewart’s sentencing, the heir to the throne of England was a 33-year-old woman named Matilda. The nascent country hadn’t encountered this particular designated survivor scenario before. In fact, the concept of a female monarch was so unknown that the word “queen” at that point meant only “the king’s wife.”

Let’s call it the Martha Stewarting of powerful women: a single-minded focus on their misdeeds, while countless men doing the same thing avoid the spotlight.

The rhetoric recorded as she attempted to rally support to take the throne is eerily prescient to the press around today’s female business and political leaders. Matilda battled for the throne against her male cousin for 18 years in a period then known as “the Anarchy.” Chroniclers of the time reported the 12th-century misogyny that prevented her from being able to rule: Matilda’s ambition, and the very concept of a female leader, was seen as unnatural. Her cunning, intelligence, and craftiness was interpreted as shrewishness. She was seen as unsympathetic for not displaying the charm or warmth of her male rival; a woman could never be a ruler, but also, couldn’t she smile more? It was Matilda who settled the Anarchy when she suggested her son take the throne as the new king; the nation, crippled from nearly two decades of war, relented. It would take more than 300 years after her death for Lady Jane Grey to become the next woman to — albeit briefly — sit on the English throne.

Hundreds of years later, our modern society is not too different. Our current equivalent of reigning monarchies, corporations, are overseen by men just as their predecessors held roles as dynastic kings and elected rulers. Most women who ascend to these ranks do so by virtue of family connections, inheriting companies or empires from male relatives or spouses. For a man to fail as a king, president, or CEO through wrongdoings is so commonplace as to be insignificant; in fact, the patriarchal system supports these men as they fall, leaving doors open for them to regain their former level of power. For a woman to ascend to these roles is novel enough, rare enough, that when they display the same fallibility or criminal activity, they dominate the news cycle for months. This when we reach peak Martha Stewarting: the particular schadenfreude expressed at the public shaming of powerful women behaving badly; the way that women who misbehave are treated as representatives for the entire gender and shamed far more than men would be for the same actions.

This double standard is similar to treatment of the mostly female victims of European witch hunts of the 15th to 18th centuries. During this time, approximately 50,000 people were put to death for alleged witchcraft. These were most often women who wielded some level of power and autonomy that caused discomfort to local magistrates. Women in many European countries at this time were not permitted to own property or control their own finances. But women with no male relatives — widows, women without children, spinsters — found ways to make ends meet on their own terms. These women ran their own businesses in fields like midwifery, herbalism, and the sorts of alternative healing popular today among female CEO Gwyneth Paltrow’s fans. The accusations made against these women were often that they had been consorting with the Devil and providing dark magic to their clients. In the Salem witch trials of 1691 and 1692, these women’s property was seized and turned over to the same men who accused and sat in judgment of them. In both the European and American instances, it wasn’t just the alleged witchcraft that led to these women being executed; it was the threat they posed to the patriarchal culture. If women were able to create their own livelihoods, to live outside of a patriarchal society, it threatened the higher status of all men — the notion of a “natural order” with men always in a superior position. Today, powerful women are still eyed suspiciously, though their trial is through the court of public opinion rather than through a Puritan tribunal.


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As rare as it is for an upper-class white woman to reach the level of success to warrant so substantive a fall from grace, it is even rarer for people of color and working-class people to attain. As such, Martha Stewarting happens primarily to wealthy white women, those whose privilege can fool them into believing their gender is a nonissue or even an advantage. That is, until they dare to make a mistake, in which case they become defined entirely by their gender — the invisible misogyny suddenly apparent. There are other double standards affecting people of all marginalized identities’ opportunities for success, in the amount or lack of support they are able to obtain for their careers, and how the media portrays them both when providing exemplary models of humanity and when breaking the law. With very few exceptions, it is wealthy white women who are able to get close enough to white male power to threaten it. And, if they threaten to make white men look foolish for following them, the Martha Stewarting comes on even more strongly as a defense mechanism to protect the woman’s former supporters.

Which brings us to former Theranos CEO Elizabeth Holmes. In March 2004, the same month that Stewart was sentenced to prison time, then 19-year-old Holmes dropped out of Stanford to focus entirely on her healthcare startup. As CEO, Holmes stood out not just for her youth and gender but also for her conventional white beauty. Like Stewart, her fresh-faced idealism and awkward persona were enmeshed with the company itself, powering media coverage for her youth and ingenuity as well as for the healthcare disruption she promised. Fifteen years later, she — like Stewart — fell entirely from grace. Holmes’s company went bankrupt and folded, and she is still facing criminal charges.

Her case has not yet been decided, but she has been vilified and pilloried by the media in a similar manner to Stewart: her downfall representing not just her personal failure, but interrogated for what it might mean for any woman who dares to take on a leadership role. Holmes’s passionate speaking style, her widely reported tendency to promise more than she was able to do, and her ability to finesse away detailed questions with braggadocio are textbook behavior for Silicon Valley start-up culture. More start-ups fail than succeed — they have about a 40% success rate. Combined with the small percentage of female-fronted Silicon Valley start-ups (26 percent of the most notable start-ups of 2018 included even one female founder), this means that male-fronted start-ups fail more than those fronted by women. Holmes’s actions, like Stewart’s — and Matilda’s — reignited debate over whether their behavior proved women were inherently unsuited for positions of leadership and power.

Holmes herself has yet to admit culpability to any of the charges she’s faced. As reporter John Carreyrou recounts, Holmes “sees herself as a sort of Joan of Arc who is being persecuted.” The parallels between accused fraudster Holmes and literal Saint Joan of Arc may not be immediately obvious. When Holmes was 19, she left Stanford and began her company. At the same age, 15th-century French peasant Joan was executed for heresy and treason following three years of leading French armies against the English. Yet they may share a similar overall trajectory: Both possessed preternatural levels of personal charisma and a single-minded determination and passion to change the world. And both went from being lauded and adored to becoming pariahs. 

Had she failed in her military campaigns, Joan’s story may have been a footnote. But she led the French in a number of campaigns that directly resulted in the coronation of King Charles VII. Under normal circumstances in Joan’s time and place, women were never entrusted with positions of power, let alone consulted on military concerns. A lower-class girl like her should have held even less sway. But Joan claimed to be in direct communication with God, her military ideas and dedication proof positive that he wanted the French dauphin to succeed in battle against the English. The people of France adored her as a heroine, but the defeated English and Burgundian troops refused to accept that they could have been bested by a young woman. They also knew that casting her as a witch and a servant of the Devil would taint King Charles’s validity. Like Martha Stewart, her prosecutors were determined to charge her with something. And so, Joan was arrested and tried for her habit of wearing men’s clothing.

She had worn men’s clothing on the battlefield, and, upon her initial imprisonment in England, continued to dress in this manner in an attempt to prevent sexual assault. While in prison, she was successfully pressured to sign a legal document disavowing her claims to have been acting on God’s orders and included a promise never to wear men’s clothing again. The circumstances upon which she was then found to have worn men’s clothing are unclear — had her captors intentionally removed her women’s clothing in order to force her to break her word and don trousers? Had Joan been forced to choose these clothes due to the ongoing threat of prison rape? Regardless of the reason, Joan is recorded as once again donning men’s clothing, and as such was found guilty of breaking her own promise. Her punishment was to burn at the stake.

By contrast, Elizabeth Holmes has settled fraud charges from the U.S. Securities and Exchange Commission, and has been indicted on nine counts of wire fraud and two counts of conspiracy to commit wire fraud. The public’s perception of her remains critical — casting her as either a devious con artist or a wide-eyed naif in over her head. Her alleged choice to intentionally lower her voice has also distracted from her legal battles to make her into a source of pop culture mockery. This vocal styling, like her androgynous presentation, seem — not unlike Joan — to be at least partly deployed in order to obscure her femininity in a male-dominated arena. Holmes is a tall, slender, conventionally attractive young white woman — as rare a Silicon Valley CEO as Joan of Arc was as a 15th-century military leader. Holmes’s affect helped her gain the trust of the male investors she needed to succeed. She was able to attract incredibly powerful male allies and supporters, many of whom continued defending her even as Theranos became exposed as a house of cards.

It is here that, outside of Holmes’s self-identification with Joan, more similarities emerge in the stories of these two women. Both have been vilified by some for their actions to an extent unlikely to befall a man who had performed the same actions; their gender has made them more hated by their accusers and critics. Holmes’s acolytes, like the defeated English nobles facing Joan, refused to accept that they had been bested by a young woman. Ultimately, the men in both instances seem to have determined that the only way this could be true is if the women in question was somehow unnatural. Joan was, therefore, a witch and a heretic. Holmes, a sociopath and a master con artist. These men may have been, in very different ways, defeated by these women, but in retroactively recasting the women as manipulative, the men were allowed to emerge as innocent. The women were both temptress and villain, the men twisting reality to retain their own sense of importance. Twenty-five years after Joan’s execution, Pope Callixtus III declared the charges against her unsubstantiated, naming Joan a martyr. In 1920, Joan was canonized as a Catholic saint, and she is now remembered for her bravery, passion, and commitment to her cause. Perhaps Holmes, whose early success predicated on her passionate declarations of wanting to save lives and improve the world, is hoping to be reconsidered similarly.

Despite strides in American feminism, women are still socialized and groomed to be complacent — we are peacekeepers, subordinate to men’s desires, not raising our voices except to back up what a man has already decided. For a woman to reach a position of power in a patriarchal structure, however, requires her to lean into the game. Traditionally feminine traits like passivity, gentleness, and nurturing will not allow a woman to take a power position. Stewart, always seen as canny and bright, was thought to have betrayed her fanbase when her calculating behind-the-scenes scheming came to light. The sweet-faced Holmes’s leadership style has, post-downfall, been consistently described as bullying. To reach the levels of power of each of these women was to act like a man; facing consequences, they are vilified in a particularly misogynistic manner.

Despite strides in American feminism, women are still socialized and groomed to be complacent — we are peacekeepers, subordinate to men’s desires, not raising our voices except to back up what a man has already decided.

Case in point: Lori Loughlin and Felicity Huffman. The actors were the most famous of the fifty people charged in the college admissions scam dubbed Operation Varsity Blues. Huffman’s lesser charges — and less tabloid-ready family — have allowed her to recede as Loughlin has become the face of privileged overreach. Loughlin and her husband have both pled not guilty, with rumors holding out that their defense will be that this practice is so commonplace neither realized they were breaking the law. Both Huffman and Loughlin have been shown to have made secret payments to admissions consultant Rick Singer; emails have been made publicly available in which both women specifically discuss their actions. Huffman pled guilty, expressing remorse for her actions. It remains to be seen if this will be her defense strategy, and if that will succeed, yet there is truth to the notion that Huffman and Loughlin’s actions are not all that different from those taken by countless wealthy parents. But it’s Loughlin’s face that was featured on tabloid covers and gossip websites. As with Stewart, the dissonance between saintly persona and criminal prosecution was too salacious to resist. When Martha Stewart was released from prison, she expressed her belief that she had been charged and jailed as “an example … that’s it.” Martha Stewarting is not just a woman facing scorn for doing something countless men get away with every day; it’s being charged with these crimes at all.

While Loughlin is best known for her acting roles, she has also been working as a producer on most of her recent TV projects. After cocreating and producing the short-lived primetime soap Summerland, Loughlin took on the role of executive producer on all of her projects for the Hallmark network beginning in 2014. Now part of the 26 percent of female executive producers on television, Loughlin focused on projects that capitalized on her mom-next-door, wholesome vibe. Unlike the more elusive Huffman, who had rarely used her persona to sell her film projects, Loughlin had married her persona to her on-screen presence, as closely as Holmes had married herself to Theranos or Stewart to her eponymous media company. So when Loughlin was charged in Operation Varsity Blues, it affected both her ability to take on acting roles (she was fired from all upcoming Hallmark projects and the final season of Fuller House), as well as her brand as a TV producer. Above all else, the contrast between her persona and her actions led to her own Martha Stewarting: public shaming that focused more on her actions than on those of her 49 co-accused parents, including her husband. 

Whatever their culpability, the charges faced by Loughlin, Huffman, Holmes, and Stewart are all backed up by evidence of their actions. Where the double standard comes in is the extent to which they have been publicly shamed for wrongdoing even as countless men have done and will continue to commit similar acts without facing the same consequences. All four women are white, heterosexual, able-bodied, and wealthy, allowing them to thrive in their lanes. However, even these privileges are not enough to protect them from our culture’s glee in watching a powerful woman fall.

The situations faced by these four women represent just one of countless no-win situations for women in our culture. Women are reprimanded for being too fat and too skinny, for being too meek and for being too confident, for failing to report a sexual assault or for bringing attention to one. When money and power enter into the equation, women are chastised for being too dependent on men or for being too much like businessmen. In all scenarios, failure becomes inevitable. The patriarchal system incentivizes greed and allows wealthy people to get away with as much as they do. In order for women to attain power, it must be within this same system, making women as fallible and corruptible as men. Yet the barometer is different for women: “Boys will be boys,” but a woman who is seen to misbehave is immediately condemned by the exact same system she’s leaned into. And it’s the culturally groomed sense of discomfort with women being in power, that it is “unnatural,” that leads to this demonization. We have been living in a false equivalency, pretending as if women can succeed in a man’s world. You can attempt to set aside your gender, like Joan of Arc and Elizabeth Holmes; you can present a sweet face to the public while working ruthlessly behind the scenes, like Martha Stewart and Lori Loughlin; but when you fail, you are nothing more than just a woman.

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Ann Foster is a writer and historian living in Saskatoon, Saskatchewan. Her research interest is in the intersection of women, history, and pop culture, especially the lives and stories of figures both well-known and half-forgotten.

Editor: Katie Kosma
Factchecker: Ethan Chiel
Copyeditor: Jacob Z. Gross

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