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Kathy Ireland sues business managers for allegedly swindling multimillion-dollar fortune

March 11, 2026
in News
Kathy Ireland sues business managers for allegedly swindling multimillion-dollar fortune

Kathy Ireland accused her former team of fumbling her multimillion-dollar fortune, according to documents obtained by Fox News Digital.

The “Sports Illustrated” cover girl claimed her former business managers betrayed her trust “on a staggering and unconscionable scale” and allegedly stole millions from Ireland and her family.

Ireland’s attorney, Jill Basinger, exclusively told Fox News Digital that Kathy’s faith hasn’t wavered since she discovered the alleged deception from within her inner circle.

“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,” Basinger said.

Basinger, Head of Media, Entertainment and Sports for Stris & Maher LLP., added that Ireland’s “faith in God is stronger than anything else.”

Kathy Ireland on the cover of the Feb. 7, 1989 Sports Illustrated.
Kathy Ireland on the cover of the Feb. 7, 1989 Sports Illustrated. Paolo Curto/S.I.

“There’s no betrayal that any human being can commit that would shake her foundation,” she continued. “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.”

In the lawsuit filed Tuesday in a Santa Barbara court, Ireland, 62 – who Forbes once estimated to be worth $420 million through her self-titled brand – claimed her family was targeted by Jason Winters and Erik Sterling, who were allegedly at the helm of a deceptive managing scheme.

“More than three decades ago, at just twenty-six years old, supermodel Kathy Ireland placed her faith — financial, professional, and personal — in two Hollywood insiders, who promised to ‘take care of everything’ for her,” the suit stated. “Kathy believed (and still does) in values and loyalty. 

Ireland poses for a portrait in 1983 in Los Angeles, California.
Ireland poses for a portrait in 1983 in Los Angeles, California. Getty Images

“At that young age, Kathy was building her career. She was newly married, planning to start a family. She believed in hard work. She believed in doing business with integrity. And, she believed in them, based on their promises to her. Tragically, that belief was misplaced. They were deceiving her, all along.”

Ireland claimed Winters and Sterling told her “she was extraordinarily wealthy” and that the family would “never need to worry.”

Instead, the model claimed her former team “failed to create wealth and make investments” as promised for their family, leaving Ireland and husband Greg Olsen in extreme debt and forced to sell their family home.

It was when the couple attempted to loan money to their son for a down payment on a home when they realized that they had no funds and the defendants used their money, according to documents. 

Ireland attends the 32nd annual Movieguide Awards Gala at AVALON Hollywood on February 07, 2025 in Los Angeles, California.
Ireland attends the 32nd annual Movieguide Awards Gala at AVALON Hollywood on Feb. 7, 2025 in Los Angeles, California. Getty Images
Ireland attends the YWCA Greater Los Angeles Rhapsody Ball held at the Regent Beverly Wilshire Hotel on November 14, 2014 in Beverly Hills, California.
Ireland attends the YWCA Greater Los Angeles Rhapsody Ball held at the Regent Beverly Wilshire Hotel on Nov. 14, 2014 in Beverly Hills, California. WireImage

“Kathy and Greg now know there are no substantial retirement accounts,” the lawsuit claimed. “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 lead to believe. 

“Instead, in the wake of Defendants misconduct, there was staggering debt, misused credit, secret loans, and missing funds.”

She believes that “the Defendants are liable to Plaintiffs for damages in the tens of millions of dollars, if not exceeding $100 million, subject to proof at trial,” documents stated. “Defendants continue to withhold the funds they took from and owe to Plaintiffs.”

The model, Olsen, and her mother, Barbara Ireland, included four former Kathy Ireland Worldwide employees.

The post Kathy Ireland sues business managers for allegedly swindling multimillion-dollar fortune appeared first on Page Six.

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