Kathy Ireland Sues Former Business Managers for Alleged Fraud

Supermodel claims 'trust betrayed on a staggering and unconscionable scale'

Mar. 11, 2026 at 11:07pm

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Kathy Ireland and her husband Greg Olsen are suing their former business managers, Jason Winters and Erik Sterling, accusing them of negligence, theft, fraud, and other allegations. The lawsuit claims the defendants concealed financial information and misused the couple's funds, leaving them with substantial debt and without the retirement savings they were promised.

Why it matters

This case highlights the risks high-net-worth individuals face when entrusting their finances to third-party managers, even those they consider family. It raises questions about the oversight and accountability of such financial relationships, as well as the importance of thorough due diligence when selecting business partners.

The details

According to the lawsuit, Winters and Sterling held themselves out as Ireland and Olsen's family for over 35 years, but allegedly concealed information and misrepresented the couple's financial situation. The lawsuit claims the defendants are liable for damages 'in the tens of millions of dollars, if not exceeding $100 million.' Ireland alleges the defendants' actions have forced her and Olsen to sell their home and left them without substantial savings or retirement funds.

  • In March 2026, Ireland and Olsen filed the lawsuit against their former business managers.
  • In October 2025, Winters alluded to a falling out with a business partner in a cryptic Instagram post, though Ireland was not named.

The players

Kathy Ireland

A celebrated model, actress, businessperson, and entrepreneur who resides in Santa Barbara, California. She found success with home decor, furniture, jewelry, and fashion products sold at various retailers.

Greg Olsen

Kathy Ireland's husband, who is also a plaintiff in the lawsuit against their former business managers.

Jason Winters

One of the former business managers being sued by Ireland and Olsen, who allegedly concealed financial information and misused the couple's funds.

Erik Sterling

The other former business manager being sued by Ireland and Olsen, who allegedly worked with Winters to conceal information and misuse the couple's funds.

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What they’re saying

“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.”

— Jill Basinger, Attorney for Kathy Ireland (Us Weekly)

“Why does a real 'relationship' fail in business? Because it wasn't real. 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.”

— Jason Winters (Instagram)

What’s next

The judge in the case will decide on whether to allow the defendants, Jason Winters and Erik Sterling, to remain out on bail.

The takeaway

This case highlights the importance of thorough due diligence and oversight when entrusting one's finances to third-party managers, even those who may be considered family. It serves as a cautionary tale about the risks of placing blind trust in business relationships and the need for greater accountability in the wealth management industry.