Former supermodel and entrepreneur Kathy Ireland has accused her longtime business managers of defrauding her of millions of dollars, according to a lawsuit filed Tuesday in Santa Barbara, California.
Ireland and her husband, Greg Olsen, filed the complaint against Jason Winters and Erik Sterling, a couple who managed their financial affairs for more than 35 years.
The suit also names Stephen Roseberry and Jon Carrasco, who held roles at Ireland's company, Kathy Ireland Worldwide, as well as Brittany Duncan, listed on business filings as the company's current chief executive.
The complaint alleges the defendants used their positions of trust to take out loans against Ireland's assets and use the money for themselves. The lawsuit says the damages could total tens of millions of dollars and potentially reach $100 million.
"In short, Defendants treated Plaintiffs as their work horses [sic] and piggy banks, all the while scheming to fund their own life style," the lawsuit states.
Ireland first rose to fame as the cover model of Sports Illustrated's record-selling 1989 Swimsuit Issue before building a large licensing business under the brand Kathy Ireland Worldwide, Variety reported.
Her name has appeared on a wide range of products, including a Kmart clothing line and home furnishings such as windows, ceiling fans, and furniture. Forbes once estimated the company's value at $420 million.
The lawsuit says Ireland did not draw a salary from the company. Instead, Winters and Sterling handled her finances and paid her expenses.
Ireland and Olsen, who worked as a physician and later as a commercial fisherman, relied on them and gave them power of attorney to manage their investments and money.
Ireland's understanding of her finances began to change when she tried to help her son with a down payment on a house, according to the complaint.
The lawsuit alleges that when she asked about available funds, Sterling and Winters became evasive and said they would need six months to liquidate her investments.
The complaint states that Ireland and Olsen eventually discovered loans had been taken out and that some or all of the money was allegedly used by the defendants themselves.
"There is no wealth securing their retirement and their children's futures, as they were led to believe," the lawsuit states. "Instead, in the wake of Defendants' misconduct, there was staggering debt, misused credit, secret loans, and missing funds."
The filing also claims the couple lost their home equity and life insurance policies and were forced to sell their home, leaving them without substantial savings.
The lawsuit also points to a social media post Winters made last October in which he hinted at tensions in the business relationship.
"The 'I will love you forever' act went on for decades, as we sipped Jim Jones-flavored Kool Aid," Winters wrote.
"We should have seen the signs. We did not."
"We were deceived. It's easy to be deceived by people you trust," added Winters.
"Whatever you hear about any situation?" he continued. "Hold your reaction until you learn the truth."
The lawsuit alleges the defendants took advantage of Ireland's loyalty while she spent decades building her brand.
Zoe Papadakis ✉
Zoe Papadakis is a Newsmax writer based in South Africa with two decades of experience specializing in media and entertainment. She has been in the news industry as a reporter, writer and editor for newspapers, magazine and websites.
© 2026 Newsmax. All rights reserved.