Former Sports Illustrated supermodel Kathy Ireland has accused her business managers of using her as a personal “piggy bank,” leaving her and her husband, Greg Olsen, deep in debt.
According to Variety, Ireland, who founded the licensing company kathy ireland Worldwide (kiWW) in 1993, filed a lawsuit in Santa Barbara on Tuesday (March 10), claiming that she and Olsen have been cheated out of their home equity and their life insurance policies. This has allegedly left them without substantial savings and forced them to sell their home.
While starting her career as a model and acting in shows such as Melrose Place and Sabrina, the Teenage Witch, Ireland found her biggest success with her own licensing company, which formed an exclusive partnership with Kmart. In 2015, Forbes valued the company at $420 milion, and in 2021, the company reportedly generated sales of $3.1 billion.
However, Ireland claims her business managers swindled her out of this income. “There is no wealth securing their retirement and their children’s futures, as they were led to believe,” the lawsuit states, per Variety. “Instead, in the wake of Defendants’ misconduct, there was staggering debt, misused credit, secret loans, and missing funds.”
Ireland and Olsen are suing Jason Winters and Erik Sterling, a couple who have managed their finances for over 35 years. They are also suing Stephen Roseberry and Jon Carrasco, a couple who worked for Ireland’s company and who were adopted as adults by Winters and Sterling. In addition, they are suing Brittany Duncan, the current CEO of kiWW.
The complaint claims that Ireland did not receive a salary from the company and that Sterling and Winters instead paid her expenses. Olsen previously worked as a doctor and later as a commercial fisherman. The couple previously gave Sterling and Winters power of attorney.
“Winters and Sterling told Kathy she was extraordinarily wealthy,” the lawsuit claims. “They told them they would never need to worry.”
Ireland first realized the true state of her finances when she tried to loan her son money for a down payment on a house. The suit alleges that Sterling and Winters became “evasive” and that Ireland and her husband later learned that the defendants had taken out loans and used the money for their own purposes.
“In short, Defendants treated Plaintiffs as their work horses and piggy banks, all the while scheming to fund their own lifestyle,” the complaint adds.
“What we have uncovered so far is just the tip of the iceberg,” Jill Basinger, Ireland and Olsen’s attorney said, per Variety. “Kathy’s managers used their position of trust to enrich themselves while constantly misleading Kathy about the state of her and her family’s financial health. The bill has come due. Sterling and Winters are going to have to answer for their actions.”
The complaint states that damages could reach as high as $100 million.
Winters alluded to the dispute in an October 2025 Instagram post, writing that business relationships fail when they aren’t “real.”
“The ‘I will love you forever’ act went on for decades, as we sipped Jim Jones-flavored Kool Aid,” he wrote. “We should have seen the signs. We did not. We were deceived. It’s easy to be deceived by people you trust.”
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