Kathy Ireland, Supermodel Turned Branding Mogul, Accuses Business Managers of Looting Her Wealth

Kathy Ireland, the Sports Illustrated swimsuit model who later made the cover of Forbes as a branding mogul, has accused her former business managers of looting millions of dollars from her and leaving her deeply in debt.

Through her licensing company, kathy ireland Worldwide, the former supermodel put her name on a Kmart clothing line and a vast array of home furnishings, including windows, ceiling fans and furniture. Forbes once estimated her company’s value at $420 million.

But according to a lawsuit filed Tuesday in Santa Barbara, Ireland and her husband have been swindled out of their home equity and their life insurance policies, forced to sell their home, and left without substantial savings.

“There is no wealth securing their retirement and their children’s futures, as they were led to believe,” the lawsuit states. “Instead, in the wake of Defendants’ misconduct, there was staggering debt, misused credit, secret loans, and missing funds.”

Ireland and her husband sued Jason Winters and Erik Sterling, a gay couple who have managed their affairs for more than 35 years. They also sued another couple, Stephen Roseberry and Jon Carrasco, who have held roles at kathy ireland Worldwide and who, according to the complaint, were adopted as adults by Winters and Sterling. They also sued Brittany Duncan, who is listed on business filings as the current CEO of kathy ireland Worldwide.

According to the complaint, Ireland did not draw a salary from the company. Instead, Sterling and Winters would pay her expenses. Her husband, Greg Olson, worked as a doctor and later as a commercial fisherman. He and Ireland trusted Winters and Sterling almost as family, giving them power of attorney and relying on them to invest their money.

“Winters and Sterling told Kathy she was extraordinarily wealthy,” the lawsuit states. “They told them they would never need to worry.”

According to the complaint, Ireland began to realize her true financial condition when she tried to loan her son money for a down payment on a house. Sterling and Winters became “evasive,” the suit alleges, saying they would need six months to liquidate her investments.

Ireland and Olson eventually came to realize that the defendants had taken out loans and then used some or all of the money for their own purposes, the suit alleges.

“In short, Defendants treated Plaintiffs as their work horses and piggy banks, all the while scheming to fund their own life style,” the lawsuit states.

The damages could run into the tens of millions of dollars, and perhaps as high as $100 million, according to the complaint.

“What we have uncovered so far is just the tip of the iceberg,” said Jill Basinger, the plaintiffs’ attorney. “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.”

In a social media post last October, Winters alluded to the falling out, writing that the Worldwide company had “sputtered and stalled abruptly, creating chaos.” Without naming Ireland directly, he said the “relationship” wasn’t real.

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

He said he had received threatening letters from lawyers, but was seeking a “peaceful resolution.” In part, he ascribed the conflict to “refusal of millionaires to cease living like billionaires, preventing others to be paid fairly.”

“Whatever you hear about any situation?” he continued. “Hold your reaction until you learn the truth.”

Winters previously worked for Elizabeth Taylor, and was rumored in 2010 to be planning to marry her. Taylor denied the rumor, and died the following year at 79. Winters has also worked with Liza Minnelli and Art Garfunkel.

Ireland has long been public about her deep Christian faith. The suit accuses Winters and the other defendants of taking advantage of her loyalty and integrity.

“The brand she built, through tireless work, travel, public appearances, licensing, and faith-based leadership, was touted as an empire,” the lawsuit states.

Now she is left to wonder how much of that success was real, and how much was a sham, the suit alleges.

“This is a betrayal at its most fundamental level,” Basinger said.

Best of Variety

Sign up for Variety’s Newsletter. For the latest news, follow us on Facebook, Twitter, and Instagram.

Zonia Grisby
Read More

Latest

Tencent Music Posts 7.3% Q1 2026 Revenue Jump, Points to Triple-Digit Live Growth and Continued Superfan Expansion

A live performance from Jay Chou, whose Children of the Sun is said to have generated about $14.7 million on Tencent Music during Q1 2026. Photo Credit: GEM_Ady Amid a continued SVIP expansion and a triple-digit revenue boost on the concerts side, Tencent Music Entertainment (TME) has reported nearly $1.2 billion in Q1 2026 revenue.

Newsletter

Don't miss

Tencent Music Posts 7.3% Q1 2026 Revenue Jump, Points to Triple-Digit Live Growth and Continued Superfan Expansion

A live performance from Jay Chou, whose Children of the Sun is said to have generated about $14.7 million on Tencent Music during Q1 2026. Photo Credit: GEM_Ady Amid a continued SVIP expansion and a triple-digit revenue boost on the concerts side, Tencent Music Entertainment (TME) has reported nearly $1.2 billion in Q1 2026 revenue.

BLXCKIE Previews New Song “Uphi Usomnyama”

MusicBLXCKIE Previews New Song “Uphi Usomnyama.” The SA...

WD sees sustainability as key business driver in an ‘AI economy’

Hard drive company WD promoted long-term operations and sustainability executive Jackie Jung to become its first chief sustainability officer in February, as it steps up sales to companies building AI data centers. Her vision: Turn sustainability into a “brand” for WD, a strategy that reduces risk for the $6 billion company (formerly known as Western

5 Business Ideas Worth Starting in 2026

If there is one thing Nigerians understand well, it is how to spot opportunity inside hardship. In 2026, that mindset will matter more than ever. The economy is tough, competition is rising, and many people are looking for smarter ways to earn, build, and survive. But even in a difficult environment, some businesses still stand

Getting a business loan now comes with a frequent flyer upside

Australian fintech Prospa has partnered with Qantas Business Rewards, letting eligible SMEs earn up to 500,000 points per loan. What’s happening: Australian fintech lender Prospa has partnered with Qantas Business Rewards to allow eligible small and medium business owners to earn up to 500,000 Qantas Points per loan when taking out a Prospa Small Business