In the summer of 2009, at a Malibu poolside gathering, Canadian heiress Taylor Thomson locked eyes with Ashley Richardson, a tall, breezy Californian with a knack for social media and a heart for spiritual causes. “Oh my God,” Thomson exclaimed, admiring Richardson’s wiry frame, “you have those fabulous heroin-chic arms.” It was an odd, cinematic line that set the tone for a friendship that would burn bright — and later, burn down.
For more than a decade, the two women became inseparable: Sunday dinners in Bel Air, holidays in Sicily, long days tending to Thomson’s beloved chickens, and star-studded nights punctuated by private fireworks on a 205-foot superyacht. They laughed, cooked, and consoled each other through deaths, divorces, and disappointments. When Thomson’s friend Beau St. Clair — a film producer and one of their mutual anchors — lay dying of ovarian cancer, she placed the women’s hands together and whispered: “Take care of each other.”
But by 2022, that promise had collapsed into a bitter courtroom feud. At the center: an $80 million cryptocurrency gamble, guided less by financial analysis than by the advice of celebrity psychics and astrologers.
Richardson lost her savings, her sobriety, and her home. She now drives for Uber. Thomson, worth an estimated $12.3 billion, says she was betrayed, manipulated, and left holding the bag. Both describe themselves as the victim of the other’s exploitation. Each insists the other destroyed their life.
The Loneliness of the Richest Family
Taylor Thomson is not just any billionaire. She is the middle child of Canada’s Thomson dynasty, whose $70+ billion fortune controls Thomson Reuters and a sprawling empire of media, real estate, and art. The family, long guarded and litigious, has been described as “Gothic” in its dysfunction: diaries shredded by lawyers, art hoarded in vaults, nannies subjected to seasonal dress codes.
Taylor grew up overshadowed by brothers who inherited both control of the business and the family’s tacit approval. She pursued acting — Shakespearean theater in Cambridge, bit parts in television — before settling into the eccentric life of an heiress. Even with staff and security, she often feared betrayal. Former employees were accused of theft. A nanny was surveilled by a notorious Hollywood PI during a custody battle.
The Thomsons’ billions insulated them from material want, but not from the vulnerabilities of intimacy. As one observer put it: “Their upbringing left them without the tools for intimate relationships. It’s a really lonely, solitary existence.”
A Friendship Worth More Than Millions
In Richardson, Taylor found something rare: not a lawyer, consultant, or opportunist, but a companion who seemed to love her for herself. They formed what Taylor called her “inner sanctum.” When Super Bowl Sunday left her alone, she left Richardson a voicemail: “I love you, we are home, you can call. Big hug, I love you, bye.”
But friendship with a billionaire is never simple. Money tilted the scales — the Nobu takeout, the yacht trips, the five-star hotels. Richardson cooked, drove, researched, and in one infamous episode, moved chickens across Los Angeles. Thomson paid the bills. It worked, until it didn’t.
The fracture came when pandemic isolation, financial stress, and the allure of quick wealth through crypto collided. Psychics predicted a “dark horse” token called Persistence would soar. At its peak, Thomson and Richardson’s holdings topped $140 million. Within a year, it was nearly worthless.
What remained was rage.
What Money Can’t Buy
It is easy to dismiss this saga as tabloid fodder — a billionaire duped by a psychic, a best friend turned Uber driver. But beneath the schadenfreude lies a profound reminder: wealth does not substitute for relationship skills.
Taylor Thomson could buy palatial estates — including a $48 million Santa Monica compound she now rents out for $250,000 a month. She could summon yachts, fireworks, or art once touched by Turner. What she could not buy was the ability to navigate the fragile terrain of trust, disappointment, and conflict with the same care she gave her gardens.
Her story echoes a truth we see daily at PAIRS: the absence of skills for listening, expressing emotions safely, clarifying expectations, and repairing ruptures leaves even the most privileged among us vulnerable to devastating breakdowns.
Without those skills, wealth magnifies mistrust. Success amplifies isolation. Pain finds its way through the cracks.
From Billions to Belonging
Taylor Thomson’s friendship with Ashley Richardson is not just a tale of bad investments; it is a parable about the cost of unskilled intimacy. When two people can’t fight fairly, can’t clarify boundaries, and can’t rebuild trust, even the deepest love curdles into accusation.
If anything, their collapse illustrates why relationship education is not a luxury, but a necessity — for billionaires and Uber drivers alike. Money can rent mansions, but it cannot secure belonging. Fortunes can purchase yachts, but not safety in love.
At PAIRS, we teach what Taylor Thomson and Ashley Richardson never learned: how to empty the jug of resentment before it explodes, how to confide without wounding, how to repair after rupture, and how to build love on purpose.
Because whether you’re holding $140 million in crypto or $14 in your checking account, the most important wealth you’ll ever have is the strength of your relationships.
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