Kathy Ireland’s managers told her she was “extraordinarily wealthy” for decades, but the truth came out when she tried to loan her son a down payment
Image by zannaland from Windermere, FL, CC BY-SA 2.0. Via Wikimedia Commons.
The moment she discovered the alleged theft is gut-wrenching.
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Kathy Ireland has filed a lawsuit against her former business managers, claiming they defrauded her of millions and left her family in serious debt, despite telling her for decades that she was financially secure. The former “Sports Illustrated” model accused her former team – Jason Winters, Erik Sterling, and Stephen Roseberry – of betraying her trust on an “unconscionable scale,” leading to major financial ruin instead of the security they had promised.
According to Fox News, the alleged deception came to light when Ireland and her husband, Greg Olsen, tried to loan their son money for a down payment on a home. That’s when they discovered there were no substantial funds available and no properly managed investments. Instead, they were reportedly facing a large amount of debt, misused credit, secret loans, and missing funds, which even forced them to sell their family home.
The lawsuit was filed in a Santa Barbara court. Ireland, now 62, says she placed her complete financial and professional trust in Winters and Sterling more than 30 years ago. At just 26 years old, she was building her career, newly married, and planning to start a family. The suit states that these “Hollywood insiders” promised to “take care of everything” for her, and allegedly told her she was “extraordinarily wealthy” and that her family would “never need to worry.”
Ireland was reportedly cheated despite placing complete trust in her financial team
Jill Basinger, Ireland’s attorney, spoke about the extent of the betrayal. She said that people simply “can’t behave like this” and that “just as a matter of human decency, it’s not right to treat someone like this.” Basinger emphasized that Kathy and Greg “put all their trust in these folks,” and their reward was to be cheated. Cases like this are a reminder of how trusted individuals can cause devastating financial harm when people place their full confidence in them.
Despite the alleged financial damage, Ireland’s attorney noted that her faith remains strong. Basinger shared that Kathy is a “strong person of faith,” and that her belief has helped her and Greg get through this betrayal. “There’s no betrayal that any human being can commit that would shake her foundation,” Basinger added.
Forbes had once estimated Ireland’s self-titled brand to be worth $420 million. The lawsuit now claims the defendants are liable for damages in the tens of millions of dollars, potentially exceeding $100 million. It also claims that the defendants continue to withhold funds they took from Ireland and her family.
The lawsuit also alleges that the defendants have not returned money they owe to Ireland. The full extent of the financial damage is still being determined as the case moves forward in court. Financial awareness matters at every level of wealth, and even everyday shoppers are finding ways to be smarter with money, like finding unexpected luxury items at low prices.
Ireland has not yet made a public statement of her own, but her attorney has made clear that she intends to hold her former managers fully accountable for what she describes as years of deliberate financial deception.
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Published: Mar 11, 2026 10:45 am