Kathy Ireland sues business managers for alleged multimillion-dollar fraud

The former model claims her former team betrayed her trust and stole millions, leaving her family in debt with no retirement savings.

Mar. 11, 2026 at 4:52am

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Kathy Ireland, the former Sports Illustrated model, has filed a lawsuit against her former business managers, Jason Winters and Erik Sterling, alleging that they betrayed her trust and swindled her out of millions of dollars over the course of decades. Ireland claims that Winters and Sterling promised to "take care of everything" for her when she was just 26 years old, but instead, they failed to create wealth and make investments as promised, leaving Ireland and her husband Greg Olsen in extreme debt and forcing them to sell their family home.

Why it matters

This case highlights the importance of carefully vetting and trusting financial advisors, especially for high-net-worth individuals like celebrities. The alleged deception by Ireland's former team raises concerns about the potential for abuse of power and trust in the entertainment and business management industry.

The details

According to the lawsuit, Winters and Sterling told Ireland that she was "extraordinarily wealthy" and that her family "would never need to worry." However, the model claims that her former team "failed to create wealth and make investments" as promised, leaving her and her husband in debt and unable to even help their son with a down payment on a home. The lawsuit alleges that the defendants are liable for damages in the tens of millions of dollars, if not exceeding $100 million.

  • More than three decades ago, when Ireland was 26 years old, she placed her trust in Winters and Sterling.
  • When Ireland and Olsen attempted to loan money to their son for a home down payment, they realized they had no funds and that the defendants had used their money.

The players

Kathy Ireland

A former Sports Illustrated model who is suing her former business managers for allegedly swindling her out of millions of dollars over decades.

Greg Olsen

Kathy Ireland's husband, who is also a plaintiff in the lawsuit.

Jason Winters

One of Kathy Ireland's former business managers, who is accused of being part of the alleged deceptive managing scheme.

Erik Sterling

Another of Kathy Ireland's former business managers, who is accused of being part of the alleged deceptive managing scheme.

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What they’re saying

“Kathy's a strong person of faith and her trust in God has really helped her and (her husband) Greg (Olsen) navigate the betrayal and the broken trust, and given her hope for the future.”

— Jill Basinger, Kathy Ireland's attorney, Head of Media, Entertainment and Sports for Stris & Maher LLP.

“There's no betrayal that any human being can commit that would shake her foundation. But that being said, people can't behave like this. And just as a matter of human decency. It's not right to treat someone like this. Kathy and Greg put all their trust in these folks. Their reward was to be cheated.”

— Jill Basinger, Kathy Ireland's attorney, Head of Media, Entertainment and Sports for Stris & Maher LLP.

What’s next

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

The takeaway

This case highlights the importance of thoroughly vetting and closely monitoring financial advisors, even for high-profile individuals like celebrities. It serves as a cautionary tale about the potential for abuse of trust and power in the entertainment and business management industry.