‘Broke’ supermodel Kathy Ireland breaks cover after suing managers

Supermodel turned branding mogul Kathy Ireland was spotted keeping a low profile while out with her family in the affluent enclave of Montecito, California earlier this week – just months after accusing her longtime managers of looting her entire fortune. 

The 63-year-old Sports Illustrated pinup broke cover for lunch with her husband, Greg Olsen, at the celebrity-loved Pierre LaFond & Co. grocery store near their home in neighboring Santa Barbara.

Shielding her face with a wide brimmed hat and donning a long flowy sundress, the apparently now-broke bombshell was all smiles despite her financial woes and looming legal battle.

Joined by one of their three adult children, Ireland and her former doctor hubby  could be seen sipping on chocolate shakes as they soaked up the Golden State sunshine. 

In an indication of the family’s current financial distress, the trio ended their outing by driving off in a small Mazda sedan – a far cry from the Mercedes they’ve previously been spotted in. 

It comes after Ireland, who rose to supermodel status in the 80s and 90s, claimed she was recently forced to sell off her family’s million home after her Hollywood managers allegedly drove her to financial ruin. 

Kathy Ireland, Sports Illustrated pinup turned branding mogul, was all smiles dining with her family in the affluent enclave of Montecito, California earlier this week – despite being embroiled in a lawsuit against her longtime Hollywood managers

The 63-year-old supermodel shielded her face with a wide brimmed hat and donned a long flowy sundress for the pitstop at at the celebrity-loved Pierre LaFond & Co. grocery store

Kathy Ireland stunned on the 1994 cover of Sports Illustrated Swimsuit Issue alongside Rachel Hunter and Elle Macpherson

In a bombshell $100 million lawsuit obtained by the Daily Mail, Ireland accused her managers, married Hollywood couple Jason Winters and Erik Sterling, of swindling her wealth over her entire career.

Ireland spent decades stacking up тιтles as an actress, author, entrepreneur, designer and philanthropist after cementing supermodel status

Ireland, who spent decades stacking up тιтles as an actress, author, entrepreneur, designer and philanthropist after cementing supermodel status, alleged she was ‘betrayed on a staggering and unconscionable scale’ after trusting the pair to handle her affairs when she started working with them in 1989. 

The long-running ‘corrupt’ mismanagement of her funds has left her staring down the barrel of mᴀssive debt with no retirement savings, according to the lawsuit filed in March. 

‘Winters and Sterling told Kathy she was extraordinarily wealthy. They told her and Greg they had financial investments securing their and their children’s futures. They told them they would never need to worry,’ the lawsuit states.

‘The world repeated those claims. The brand she built, through tireless work, travel, public appearances, licensing, and faith-based leadership, was touted as an empire.’ 

‘But while Kathy’s tireless work and integrity was real, and while the value of the brand and the business and gross income she and Greg generated surely could and should have left them with wealth and financial security for their retirement years, the corrupt [managers’ management of the money was a sham.’ 

Ireland was joined by her husband of 38 years, Greg Olsen, and their oldest daughter Lily for the outing

At one point, Ireland could be seen sipping on a chocolate shake as she soaked up the Golden State sunshine with her family

The sighting comes after Ireland claimed she was recently forced to sell off her family’s million home after her Hollywood managers allegedly drove her to financial ruin

Ireland, who rose to supermodel status in the 80s and 90s, was spotted keeping a low profile amid her ongoing legal and financial woes

EXCLUSIVE Iconic ‘girl next door’ of the 1960s who worked with Elvis Presley surfaces at age 84… guess who?

Having graced the Sports Illustrated cover three times, the bombshell launched kathy ireland Worldwide (kiWW) back in 1993, quietly building a retail empire that would make her one of the wealthiest models on the planet.

At one point, Forbes – who dubbed Ireland a ‘super mogul’ – estimated her net worth to be roughly $420 million.  

As Ireland traveled the world and her husband worked grueling shifts in the emergency room, the managers promised to take care of all of the couple’s personal and financial affairs, the lawsuit alleges. 

‘Winters and Sterling induced [the couple] to grant them powers-of-attorney and to give them full reign over all of their personal finances and income,’ the court filings state. 

‘Winters and Sterling took absolute control over all aspects of the financial affairs of Kathy and Greg, promising to do right by them and make them wealthy.’

‘Based on the promises made by Winters and Sterling, Kathy and Greg believed they had millions of dollars invested by Winters and Sterling and that they had extremely significant net worth,’ the suit added. 

Ireland and her former doctor hubby allege her managers promised to take care of all of the couple’s personal and financial affairs but ended up mismanging it all, the lawsuit alleges  

Ireland alleges Jason Winters and Erik Sterling (pictured in the middle) are liable for damages ‘in the tens of millions of dollars, if not exceeding $100 million’, according to the court papers

At one point, Forbes – who dubbed Ireland a ‘super mogul’ – estimated Ireland’s net worth to be roughly $420 million. She is pictured above at the Academy Awards in 2010

But the alleged ruse came crashing down when the couple, who have been married 38 years, recently tried to help their son buy a home – only to find their application to co-sign on a ‘modest mortgage’ had been denied.

‘Kathy and Greg now know there are no substantial retirement accounts. There are no prudently managed investments securing their future, as promised,’ the court papers state. 

‘There is no wealth securing their retirement and their children’s futures, as they were lead [sic] to believe. Instead, in the wake of [the managers’] misconduct, there was staggering debt, misused credit, secret loans, and missing funds.’

The lawsuit alleges the Hollywood managers are liable for damages ‘in the tens of millions of dollars, if not exceeding $100 million.’

The Daily Mail reached out to Winters and Sterling for comment. 

In a scathing statement shortly after the lawsuit was first filed, the current CEO of kiWW, Brittany Duncan, blasted the legal action as a ‘frivolous’ attempt to dodge a pending $25 million fraud lawsuit. 

‘That litigation stems from a matter of fraud, allegedly committed by Ireland, that was exposed and filed in 2025. Ireland’s new lawsuit is apparently a publicity-seeking effort to evade Ireland’s financial and legal responsibilities,’ Duncan said in a statement posted online. 

The circumstances involving that pending lawsuit weren’t immediately clear.