‘Dancing With the Stars’ Alum Seeks $100 Million or More in Lawsuit

Kathy Ireland is suing her former business managers for allegedly using her personal fortune as their “piggy bank,” as she claims damages of as much as $100 million.

The Sports Illustrated model, who appeared on Season 9 of Dancing With the Stars, filed a lawsuit on Tuesday in Santa Barbara, Calif., in which she claims that her former business managers left her and her husband, Greg Olsen, deeply in debt, swindled out of their home equity and life insurance policies and forced to sell their home without substantial savings to their name.

In the lawsuit, obtained by Variety, Ireland and her husband accuse Jason Winters and Erik Sterling, a couple who managed their finances for more than 35 years, of financial impropriety. Also included in the complaint are Stephen Roseberry and Jon Carrasco, another couple who held roles at Ireland’s licensing company, kathy ireland Worldwide, and who were allegedly adopted by Winters and Sterling as adults. Brittany Duncan, the current CEO of kathy ireland Worldwide, is also listed on the lawsuit.

The model and business founder, who Forbes once estimated to be worth about $420 million, claims in the suit that her trust was betrayed “on a staggering and unconscionable scale” by her former business managers, and that instead of “wealth securing their retirement and their children’s futures,” Ireland and Olsen are left with only “staggering debt, misused credit, secret loans, and missing funds.”

In the complaint, Ireland claims she did not receive a salary from her company, and that her expenses were instead paid by Sterling and Winters. It was only when she went to loan her son money for a house payment that Ireland claims she discovered the true state of her finances, as she alleges that the defendants had taken out loans and used the money for their own lifestyle.

“In short, Defendants treated Plaintiffs as their work horses and piggy banks, all the while scheming to fund their own lifestyle,” the complaint alleges.

“What we have uncovered so far is just the tip of the iceberg,” Jill Basinger, Ireland and Olsen’s attorney, said, as per Variety. “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.”

Winters alluded to a business dispute in October 2025 in an Instagram post calling out one particular professional relationship as not “real.”

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

After receiving threatening letters from attorneys, Winters wrote that he was seeking “peaceful resolution,” claiming that the issue stemmed from the “refusal of millionaires to cease living like billionaires, preventing others to be paid fairly.”

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