Kathy Ireland, the former supermodel who built a major branding empire after her runway and magazine career, was seen out with family in upscale Montecito, California, this week, keeping a relatively discreet profile months after filing explosive claims that her longtime managers allegedly drained her fortune.
Ireland, 63, best known to many as a former Sports Illustrated favorite, stepped out for lunch with her husband, Greg Olsen, at Pierre LaFond & Co, the celebrity-frequented grocery and café near their home in neighboring Santa Barbara.
Wearing a wide-brimmed hat that partly concealed her face and a long, flowing sundress, Ireland appeared relaxed and upbeat despite the financial allegations and legal fight now surrounding her business affairs.
The couple were joined by one of their three adult children, Lily, and the trio appeared to enjoy chocolate shakes while spending time together in the Southern California sunshine.
Their departure drew attention as well: the family left in a compact Mazda sedan, a noticeably more modest vehicle than the Mercedes in which they had previously been seen.
The outing follows Ireland’s claim that she was recently compelled to sell her family’s million-dollar home after accusing her longtime Hollywood managers of pushing her into severe financial distress.
Kathy Ireland, the Sports Illustrated alum turned branding entrepreneur, was seen smiling during a family outing in Montecito, California, as she remains involved in a lawsuit against her longtime Hollywood managers
The 63-year-old former supermodel wore a wide-brimmed hat and a flowing sundress during a stop at Pierre LaFond & Co, a grocery and café popular with celebrities
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 career.
Ireland spent decades stacking up titles as an actress, author, entrepreneur, designer and philanthropist after cementing supermodel status
Ireland, who spent decades stacking up titles 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 massive 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
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-dollar 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
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 former doctor 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 mismanaging it all, the lawsuit alleges
Ireland alleges Jason Winters and Erik Sterling (center) 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
But the alleged ruse came crashing down when the couple, who have been married for 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, chief executive 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.
The circumstances involving that pending lawsuit weren’t immediately clear.
