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.

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