Kathy Ireland Sues Business Managers for Allegedly Looting Millions

The former supermodel claims her longtime business partners misused funds and left her deeply in debt.

Mar. 10, 2026 at 1:51pm

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Kathy Ireland, the former Sports Illustrated swimsuit model who built a successful branding empire, has sued her longtime business managers Jason Winters and Erik Sterling, accusing them of looting millions of dollars from her company and leaving her and her family deeply in debt. The lawsuit alleges the defendants misused Ireland's home equity, life insurance policies, and other funds to fund their own lavish lifestyles.

Why it matters

This case highlights the risks celebrities and high-net-worth individuals face when entrusting their finances to close business partners, even those they've worked with for decades. It raises questions about oversight, accountability, and the need for stronger safeguards to protect vulnerable clients from potential financial exploitation by trusted advisors.

The details

According to the lawsuit, Winters and Sterling, a gay couple who managed Ireland's affairs for over 35 years, allegedly took out secret loans, misused credit, and siphoned off funds, leaving Ireland and her husband Greg Olson without substantial savings or wealth to secure their retirement. The suit also names two other associates, Stephen Roseberry and Jon Carrasco, who were allegedly adopted as adults by Winters and Sterling.

  • The lawsuit was filed on Tuesday, March 10, 2026.

The players

Kathy Ireland

A former Sports Illustrated swimsuit model who built a successful branding and licensing empire, kathy ireland Worldwide.

Jason Winters

One of Ireland's longtime business managers who is accused of looting millions of dollars from her company.

Erik Sterling

The other longtime business manager of Ireland's who is accused of looting millions of dollars from her company.

Greg Olson

Ireland's husband, who worked as a doctor and commercial fisherman and trusted Winters and Sterling to manage the couple's finances.

Brittany Duncan

The current CEO of kathy ireland Worldwide, who is named as a defendant in the lawsuit.

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What’s next

The lawsuit seeks tens of millions of dollars in damages, and the plaintiffs' attorney says the full extent of the alleged misconduct is still being uncovered.

The takeaway

This case underscores the importance of rigorous financial oversight, even for high-profile celebrities and business leaders, and the need to guard against potential exploitation by trusted advisors. It serves as a cautionary tale about the risks of over-relying on close business partners to manage one's personal and professional finances.