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The Untold Story Of Linda O’Leary: 5 Shocking Facts About Mr. Wonderful’s Wife, From Boardroom To Boat Crash

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For decades, the business world has known Kevin O'Leary as "Mr. Wonderful," the sharp-tongued investor from *Shark Tank* and the co-founder of SoftKey Software Products. However, behind the relentless pursuit of profit and his public persona is a 35-year marriage to a woman who is a successful businesswoman in her own right: Linda O'Leary. As of late 2025, the O'Learys continue to navigate their complex life, which is split between high-stakes marketing, family life, and the lingering shadow of a highly publicized legal battle that captivated Canada and the United States. Linda O'Leary is far more than just a celebrity spouse; she is a high-ranking executive, a dedicated patron of the arts, and the anchor of the O'Leary family. Her life story is a fascinating blend of entrepreneurial partnership, personal resilience, and public scrutiny, making her one of the most intriguing figures in the orbit of the *Shark Tank* universe. This deep dive uncovers the essential facts about the woman who has stood by Kevin O'Leary through his rise to global fame and fortune.

Linda O'Leary: Complete Biography and Professional Profile

Linda O'Leary, born Linda Greer, has maintained a relatively private life despite her husband's intense public profile, but her own accomplishments and personal history are significant.
  • Full Name: Linda O'Leary (née Linda Greer)
  • Spouse: Terrence Thomas Kevin O'Leary (Kevin O'Leary)
  • Date of Marriage: 1990 (Over 35 years of marriage as of 2025)
  • Children: Daughter Savannah O'Leary (born 1993) and Son Trevor O'Leary (born 1996)
  • Education: Attended the University of Toronto (U of T)
  • Current Professional Role: Vice President of Marketing for O'Leary Wines
  • Other Roles: Board Member of O'Leary Wines, Founding Chair of the Esprit de Corps for the National Ballet of Canada
  • Primary Residence: Toronto, Canada (with properties in Boston and Muskoka, Ontario)
Linda O'Leary's professional career has been deeply intertwined with her husband's ventures, particularly in the wine industry. She is credited with playing an integral role in the branding and market positioning of O'Leary Wines since its launch in 2016, where she currently serves as the Vice President of Marketing.

The Secret to a 35-Year Partnership: Business and Marriage

The marriage between Kevin and Linda O'Leary is a testament to resilience, having weathered both the extreme pressures of the business world and a brief separation. The couple first met in the late 1980s at a party thrown by Kevin's roommates while Linda was a student at the University of Toronto. They married in 1990, just as Kevin O'Leary was laying the groundwork for his first major success with SoftKey. Kevin O'Leary has often been candid about the challenges of balancing a demanding entrepreneurial life with marriage, famously stating that "marriages are collateral damage in the relentless drive to get rich." Despite this, the O'Learys found a way to make their union work, even after a two-year separation. They reconciled, a decision Kevin has attributed to the realization that family was more important than the sole pursuit of wealth. Their philosophy on marriage often mirrors Kevin's business acumen, viewing it as a continuous journey that requires constant respect and mutual investment, not a final destination. This partnership has extended into their professional lives, most notably with O'Leary Wines.

Linda O'Leary's Pivotal Role at O'Leary Wines

While Kevin O'Leary is the public face of the brand, Linda O'Leary is the strategic mind behind its market presence. As the Vice President of Marketing for O'Leary Wines, she is responsible for the company's brand identity, consumer outreach, and overall market strategy. Her work has been crucial in positioning the brand, which partners with Vintage Wine Estate, in a highly competitive market. Linda's passion for the arts and culture, which she actively supports, also informs her marketing approach, adding a layer of sophistication to the O'Leary Wines portfolio.

The Boat Crash Controversy: A Defining Public Battle

The most significant public event involving Linda O'Leary in recent years was the tragic boat crash on Lake Joseph in Muskoka, Ontario, in August 2019. This incident thrust her into the international spotlight under intense scrutiny.

The Incident and Legal Proceedings

The crash occurred when the O'Leary boat, which Linda O'Leary was operating, collided with another vessel on the lake, resulting in the deaths of two people and injuries to others. * The Charge: Linda O'Leary was charged with careless operation of a vessel under the Canada Shipping Act. * The Defense: Her defense maintained that the other boat was operating without proper navigation lights, making it invisible on the dark lake. * The Verdict: In September 2021, a judge found Linda O'Leary not guilty of the charge. The court determined that the prosecution failed to prove beyond a reasonable doubt that she was operating the boat without proper care or consideration for others. This legal battle was a profound test of the O'Leary family's resilience and became a major media story, highlighting the personal risks that can accompany a life of high-profile wealth.

The O'Leary Children: Savannah and Trevor

The O'Learys have successfully raised two adult children, both of whom have carved out their own paths, often appearing alongside their famous parents at public events. * Savannah O'Leary: Born in 1993, Savannah has pursued a career in the film and media industry. * Trevor O'Leary: Born in 1996, Trevor has shown an interest in his father's entrepreneurial spirit and has been involved in various projects. Kevin O'Leary has often spoken about Trevor's work in the tech and venture capital space. The O'Leary family maintains a strong bond, often spending time together at their various properties, including their main home in Toronto and their cottage in the Muskokas.

Linda O'Leary's Commitment to the Arts

Beyond the business world, Linda O'Leary is a passionate advocate for the arts, particularly in Canada. Her dedication to culture is a less-publicized but important aspect of her life. She is the Founding Chair of the Esprit de Corps for the National Ballet of Canada, a role that demonstrates her commitment to supporting and fostering artistic talent. This philanthropic work aligns with her personal passion for art, which she often shares on social media, showcasing her support for the arts community. In conclusion, Linda O'Leary is a multifaceted figure whose life is defined by a deep partnership, significant professional contributions as the VP of Marketing for O'Leary Wines, and immense personal strength demonstrated during the highly-publicized boat crash trial. Her story is a compelling counter-narrative to her husband's "Mr. Wonderful" persona, revealing the solid foundation of family and business acumen that underpins one of the world's most recognizable entrepreneurial empires.
kevin o leary wife
kevin o leary wife

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