Kathy Ireland, a lifelong Santa Barbara resident who rose to fame as a Sports Illustrated Swimsuit model before building a global licensing empire, has sued her former business managers for allegedly plundering her multimillion-dollar fortune.
According to the lawsuit filed March 9 in Santa Barbara County Superior Court, the long-running deception left Ireland in “massive debt” with no retirement savings, and forced the sale of her family home. The complaint claims her managers ― married Hollywood couple Jason Winters and Erik Sterling, who operated kathy ireland Worldwide (kiWW) for more than 30 years ― are liable for damages “in the tens of millions of dollars, if not exceeding $100 million.”
“This case is about trust betrayed on a staggering and unconscionable scale,” states the lawsuit filed on behalf of Ireland and her family by Santa Barbara attorney Jared M. Katz with the law firm Mullen & Henzell. “Defendants have not merely mismanaged money. They had consolidated control over Kathy and [husband Greg Olsen] through a tightly interwoven network of personal and corporate relationships designed to obscure accountability.”
Also named as defendants are Brittany Duncan, current CEO of kiWW, and Stephen Roseberry and Jon Carrasco, another couple whom the complaint says Winters and Sterling adopted as adults.
None of their attorneys responded to requests for comment, but a public LinkedIn statement by Duncan described Ireland’s lawsuit as “a publicity-seeking effort” tied to an ongoing $25 million dispute among the parties. Duncan called the allegations “knowingly false, baseless, deceptive, slanderous, and disingenuous,” and she challenged Ireland’s identity as a “Christian philanthropist.” “Kathy Ireland may be spiritually broken, but she is not financially ‘broke,’” Duncan claimed.
Ireland hired Winters and Sterling in 1989, soon after she married Olsen, a now-retired Cottage Hospital trauma surgeon who has since become a commercial fisherman. The business relationship grew into a close friendship.
Ireland, 26 years old at the time, granted the pair power of attorney and “complete control” over her finances, relying heavily on their guidance as her career took off, which included extensive travel, public appearances, faith-based engagements, and licensing negotiations with clothing, jewelry, and furniture retailers.
“She believed in hard work,” the lawsuit states. “She believed in doing business with integrity. And, she believed in them, based on their promises to her. Tragically, that belief was misplaced.”
Winters and Sterling told Ireland her earnings were being invested and assured her repeatedly over the years that she and her family were “extraordinarily wealthy,” the suit says. “They told her and Greg they had financial investments securing their and their children’s futures. They told them they would never need to worry.”
Instead, the complaint alleges, the pair opened multiple credit cards in Ireland’s name (as well as as a housekeeper’s name), ran up huge debts, and only paid minimum balances. They also reportedly took out “secret loans” and deceptively transferred funds.
Winters and Sterling “seized and commingled funds,” the complaint goes on. “They failed to keep records. They placed their own family members and adopted adult ‘children’ into fiduciary and business roles, using them as a buffer to hide from accountability. They cultivated a cabal of inter-familial relationships that blurred personal loyalty and fiduciary duty. … Their message was clear: this was not a business subject to oversight; it was a ‘family’ never to be questioned.”
Ireland and Olsen’s illusion of financial security was shattered when they attempted to co-sign a mortgage for their son. “They believed they had impeccable credit and significant liquidity,” the suit says. “Instead, they were shocked when their application was denied.”
When Ireland pressed Winters and Sterling for an explanation, their responses were reportedly “manipulative, evasive, and subversive.” Ireland tried for six months to get answers before finally pursuing legal action.
In an interview with ABC News, Ireland acknowledged her decision to place so much faith in Winters and Sterling may have been “naive.” But she’s no longer willing to turn the other cheek. “My old job description was ‘shut up and pose.’ And I reject that,” she said. “I’m not going to idly stand by and allow anyone to lie, to abuse, to hurt my family, and to hurt others.”
Ireland’s case, still in its very early stages, is scheduled for its next court hearing on July 8 before Judge Thomas Anderle.
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