Kathy Ireland Sues Longtime Managers for Alleged $100M Theft

The model and entrepreneur claims her business managers misused funds, leaving her and her husband deep in debt.

Mar. 10, 2026 at 2:35pm

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Former model and entrepreneur Kathy Ireland has filed a lawsuit accusing her longtime business managers of misusing her finances, allegedly taking out secret loans and siphoning off up to $100 million of her wealth. Ireland claims she and her husband were deceived about their true financial status and are now left deep in debt, forced to sell their home.

Why it matters

This case highlights the risks celebrities and high-net-worth individuals face when entrusting their finances to managers, and the potential for abuse of that trust. It also raises questions about oversight and accountability for those managing the fortunes of the wealthy.

The details

According to the lawsuit, Ireland's managers Jason Winters and Erik Sterling, along with others they were associated with, secretly took out loans, misused funds, and left Ireland and her husband Greg Olsen with significant debt. The couple previously gave Winters and Sterling power of attorney over their finances.

  • On March 10, 2026, Ireland filed the lawsuit in Santa Barbara, California.
  • In October 2025, Winters alluded to the dispute in an Instagram post.

The players

Kathy Ireland

A former model and actress who founded the licensing company kathy ireland Worldwide (kiWW), which was valued at $420 million in 2015 and reportedly generated $3.1 billion in sales in 2021.

Greg Olsen

Ireland's husband, who previously worked as a doctor and commercial fisherman.

Jason Winters

One of Ireland's longtime business managers, who was adopted as an adult by Erik Sterling.

Erik Sterling

One of Ireland's longtime business managers, who was adopted as an adult by Jason Winters.

Brittany Duncan

The current CEO of kathy ireland Worldwide.

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What they’re saying

“What we have uncovered so far is just the tip of the iceberg. 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.”

— Jill Basinger, Ireland and Olsen's attorney (Variety)

“The 'I will love you forever' act went on for decades, as we sipped Jim Jones-flavored Kool Aid. We should have seen the signs. We did not. We were deceived. It's easy to be deceived by people you trust.”

— Jason Winters (Instagram)

What’s next

The judge in the case will decide on whether to allow the defendants out on bail.

The takeaway

This case highlights the importance of thorough oversight and accountability when entrusting financial management to third parties, even long-time associates. It serves as a cautionary tale for celebrities and the wealthy to closely monitor their finances and be wary of potential abuse of trust.