Kathy Ireland Sues Longtime Business Managers, Alleges They’re Liable for $100 Million in Damages

Kathy Ireland and her husband, Greg Olsen, are suing their former business managers.

According to court documents obtained by Us Weekly in March 2026, Ireland and Olsen accuse multiple defendants of negligence, theft, intentional representation, constructive fraud and other allegations.

“This case is about trust betrayed on a staggering and unconscionable scale,” the lawsuit claims. “For over 35 years, defendants Jason Winters and Erik Sterling held themselves out to Kathy and Greg, not only as their managers, but as their family. … But in fact, they concealed and misrepresented information from Kathy and Greg to hide their predatory misdeeds.”

According to the lawsuit, Ireland claims the defendants are liable for damages “in the tens of millions of dollars, if not exceeding $100 million.” (According to Forbes, Kathy Ireland Worldwide generated retail sales of $3.1 billion in 2021 alone.)

“My clients granted sweeping authority to people who concealed the truth while exercising total financial control and enriching themselves. Their conduct will be exposed, and it will have consequences,” Ireland’s attorney, Jill Basinger of Stris & Maher LLP, said in a statement to Us. “The scale and sophistication of this fraud demand an equally sophisticated response. We are pursuing this matter aggressively. The defendants are not facing a garden-variety dispute — they are facing comprehensive scrutiny that will expose what has been hidden for years. This is a serious reckoning.”

Keep reading to read more of Ireland and Olsen’s shocking claims in the lawsuit:

Who Is Kathy Ireland?

In the lawsuit, Kathy Ireland is described as a “celebrated model, actress, business person and entrepreneur” who resides in Santa Barbara, California.

Over the years, Ireland found success with home decor, furniture, jewelry and fashion. Her items can be found at various stores, including HSN, Home Depot and Walmart.

What Is Kathy Ireland and Greg Olsen Accusing the Defendants of Doing? 

According to court documents obtained by Us, Kathy Ireland and Greg Olsen “do not know the whole story” of what they could have lost because of the defendants’ alleged actions.

“Kathy and Greg now know there are no substantial retirement accounts,” the lawsuit claims. “There are no prudently managed investments securing their future, as promised. There is no wealth securing their retirement and their children’s futures, as they were led to believe. Instead, in the wake of Defendants misconduct, there was staggering debt, misused credit, secret loans and missing funds.”

Ireland and her husband claim they’ve been forced to sell their home and have been left without substantial savings, court documents state.

“Defendants treated Plaintiffs as their work horses and piggy banks, all the while scheming to fund their own lifestyle, while hanging the Ireland-Olsen family out to dry,” the lawsuit alleges.

How Close Were Kathy Ireland and Her Business Managers?

One year after marrying Greg Olsen, Kathy Ireland started working with Jason Winters and Erik Sterling as her managers.

“Over the years, Winters continually preached to Kathy and Greg about the great personal ‘wealth’ he and Sterling were creating for them, and the very successful financial ‘investments’ he and Sterling were managing for them,” the lawsuit alleges. “Kathy always believed Winters and Sterling because she trusted them. Greg also believed they were working in Kathy’s and his best interests.”

Court docs also allege Winters and Sterling (who are married) claimed they “loved” Ireland and Olsen.

“Based on the promises made by Winters and Sterling, Kathy and Greg believed they had millions of dollars invested by Winters and Sterling and that they had extremely significant net worth,” the suit alleges. “When Plaintiffs asked about their financial condition, Winters and Sterling scoffed at them, telling them they were so extremely wealthy and successful that they would never have anything to worry about.”

What Have the Defendants Said About the Case

Although Jason Winters and Erik Sterling have yet to publicly comment on the suit, Winters alluded to a falling out with a business in a cryptic Instagram post. (Kathy Ireland was not named in the social media post.)

“Why does a real ‘relationship’ fail in business? Because it wasn’t real,” Winters wrote in October 2025. “We should have seen the signs. We did not. We were deceived. It’s easy to be deceived by people you trust. Especially, when decades of faith, success and love appear wrapped in a faux-relationship older than my grandchildren. …. Whatever you hear about any situation? Hold your reaction until you learn the truth.”

Us has reached out to Winters and Sterling’s attorney for comment.