Just weeks after she publicly reflected on “betrayal” and misplaced trust in business relationships, model-turned-business mogul Kathy Ireland is suing her former business managers, alleging they looted millions of dollars from her finances and left her family in debt.
The lawsuit, filed Tuesday in Santa Barbara County Superior Court, accuses longtime managers Jason Winters and Erik Sterling of orchestrating a decades-long scheme that allegedly drained Ireland’s wealth, saddled her family with debt and concealed the true state of her finances for more than 35 years.
Ireland and her husband, physician and commercial fisherman Greg Olsen, claim the men exploited the couple’s trust after being granted sweeping control over their personal finances and business operations.
“This case is about trust betrayed on a staggering and unconscionable scale,” the complaint states.
Ireland rose to fame as a supermodel in the 1980s and 1990s, after appearing in multiple editions of the Sports Illustrated swimsuit issue before transitioning into a highly successful business career. Through her company, kathy ireland Worldwide, she built a global licensing empire spanning apparel, home furnishings and lifestyle products.
At one point, Forbes estimated the brand’s value at roughly $420 million.
“Founded in 1993, kathy ireland Brands has grown into one of the world’s most powerful licensing empires, celebrated by Forbes as ‘Supermodel Turned Super Mogul.’ Spanning fashion, home furnishings, wellness, fintech, and more, the brand has been recognized by Women’s Wear Daily as the most valuable woman-owned licensing company in American history,” notes the brand’s website.
But the lawsuit alleges that behind the image of financial success was a hidden reality: Ireland and Olsen say they were left without substantial retirement savings, forced to sell their home and burdened by secret loans and damaged credit.
“There are no substantial retirement accounts,” the filing reads. “There is no wealth securing their retirement and their children’s futures, as they were led to believe.”
Instead, the complaint alleges “staggering debt, misused credit, secret loans and missing funds.”
Ireland, Olsen and Ireland’s mother, Barbara Ireland, are listed as plaintiffs in the case.
According to the complaint, Ireland first began working with Winters and Sterling when she was 26 years old. The pair allegedly positioned themselves not only as managers but as trusted family members, eventually receiving power of attorney and control over the couple’s finances, investments and retirement planning.
Ireland did not draw a salary from her company, the lawsuit claims. Instead, Winters and Sterling told her that the income generated from her brand, including licensing deals, speaking engagements and product partnerships, was being invested on her behalf.
Her husband also entrusted his earnings to the same financial structure, according to the suit. Olsen worked both as an emergency room physician and as a commercial fisherman operating the company 4th Watch Seafood.
The lawsuit alleges those funds were also misused.
Ireland and Olsen say they first began questioning their finances when they attempted to co-sign a mortgage for their son and were denied due to poor credit. They claim they were stunned to learn they could not access the wealth they had been assured existed.
“When Kathy pressed for answers,” the lawsuit states that Winters and Sterling allegedly became evasive, claiming the investments were complex and would take months to liquidate.
The plaintiffs say they later discovered loans had allegedly been taken out in their names and that money had been diverted to fund the defendants’ personal lifestyles.
“In short, Defendants treated Plaintiffs as their workhorses and piggy banks,” the lawsuit alleges.
The suit names several additional defendants, including Stephen Roseberry and Jon Carrasco, described in the complaint as adopted adult children of Winters and Sterling, along with Brittany Duncan, who business records list as the current CEO of kathy ireland Worldwide.
The complaint accuses the defendants of creating a network of personal and corporate relationships designed to obscure financial accountability while consolidating control over Ireland’s finances and business empire.
The lawsuit seeks damages that could reach tens of millions of dollars and potentially as high as $100 million, according to the complaint.
Attorney Jill Basinger, who represents Ireland and Olsen, said investigators believe the alleged misconduct may extend beyond what has been uncovered so far.
“What we have uncovered so far is just the tip of the iceberg,” Basinger said in a statement. “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.”
Winters previously publicly suggested that a falling-out had occurred between the parties.
In a social media post last October, he wrote that the business relationship had deteriorated and described the company as having “sputtered and stalled abruptly, creating chaos,” according to a report from Variety.
Without naming Ireland directly, he wrote that the “relationship” between them was not real. He also suggested the dispute stemmed in part from disagreements over financial expectations, accusing the couple of being millionaires who wouldn’t stop living like billionaires.
“Whatever you hear about any situation?” he wrote. “Hold your reaction until you learn the truth.”
Winters previously worked with several high-profile celebrities, including the late actress Elizabeth Taylor, and performers Liza Minnelli and Art Garfunkel.
Ireland, who has long spoken publicly about her Christian faith, has said difficult business experiences have shaped her spiritual perspective.
In a February interview with The Christian Post, she said she’d experienced “betrayal” in business but acknowledged the pain can come from broken trust, emphasizing her reliance on faith.
“Business is hard, and throughout the decades, we have had our ups and downs, and there’s been betrayal, there’s been misplaced trust, there’s been a lot,” she said. “It’s hard, but God has taught me the importance of the inerrancy of His word and to grow in Him and not to remain a baby Christian like I did for so many years.”
Ireland said she has learned to anchor her identity in her faith rather than in financial success or circumstances.
“I am good because God is good, and I’m not my circumstances,” she said. “Even when you’re going through a hard situation, that doesn’t define me.”
The lawsuit seeks restitution for alleged financial elder abuse, recovery of misappropriated funds and a full accounting of the couple’s finances after decades under the defendants’ management.
“This is not a dispute over a failed investment,” the complaint states. “It is about fiduciaries who obtained absolute control over their clients’ life and finances, falsely assured them they were secure, lied and left them in turmoil.”
The Christian Post reached out to Jason Winters and kathy ireland Worldwide for comment but did not receive a response by the time of publication. This article will be updated if a response is received.
Leah M. Klett is a reporter for The Christian Post. She can be reached at: [email protected]
