{"id":227667,"date":"2026-03-10T21:55:05","date_gmt":"2026-03-10T21:55:05","guid":{"rendered":"https:\/\/entertainment.runfyers.com\/index.php\/2026\/03\/10\/kathy-ireland-is-suing-former-business-managers-claims-decades-of-financial-misconduct-resulting-in-severe-debt\/"},"modified":"2026-03-10T21:55:05","modified_gmt":"2026-03-10T21:55:05","slug":"kathy-ireland-is-suing-former-business-managers-claims-decades-of-financial-misconduct-resulting-in-severe-debt","status":"publish","type":"post","link":"https:\/\/entertainment.runfyers.com\/index.php\/2026\/03\/10\/kathy-ireland-is-suing-former-business-managers-claims-decades-of-financial-misconduct-resulting-in-severe-debt\/","title":{"rendered":"Kathy Ireland is Suing Former Business Managers, Claims Decades of Financial Misconduct Resulting in Severe Debt"},"content":{"rendered":"<p> <br \/>\n<\/p>\n<div id=\"\">\n<p><a href=\"https:\/\/www.justjared.com\/tags\/kathy-ireland\/\" title=\"Kathy Ireland\" target=\"_blank\" rel=\"noopener\"><strong>Kathy Ireland<\/strong><\/a> is suing her former business managers over allegations that they swindled millions of dollars from her, leaving her and her family deeply in debt.<\/p>\n<p>The former <em>Sports Illustrated<\/em> swimsuit model launched her brand licensing company kathy ireland Worldwide (kiWW) in 1993, beginning with an exclusive deal with Kmart that included her own clothing line. <\/p>\n<p>She later cut ties with the department store to become a global licensor and has been hailed as one of Forbes 50 most successful self-made women with her company generating billions in profit in 2021. <\/p>\n<p>In a lawsuit filed on Tuesday (March 10) in Santa Barbara, Calif., <strong>Kathy<\/strong> and her husband <strong>Greg Olson<\/strong> accuse married couple <strong>Jason Winters<\/strong> and <strong>Erik Sterling<\/strong> of looting their wealth, shares <a href=\"https:\/\/variety.com\/2026\/biz\/news\/kathy-ireland-lawsuit-business-managers-looting-1236681426\/\" onclick=\"getOutboundLink(&#039;https:\/\/variety.com\/2026\/biz\/news\/kathy-ireland-lawsuit-business-managers-looting-1236681426\/&#039;); return false;\" target=\"_blank\" rel=\"noopener\">Variety<\/a>.<\/p>\n<p><strong class=\"hidearticle\"><em>Keep reading to find out more\u2026<\/em><\/strong><span id=\"more-2187798\"><\/span><\/p>\n<p><strong>Sterling<\/strong> and <strong>Winters<\/strong> managed the couple\u2019s finances for more than 35 years and had gained <strong>Kathy<\/strong> and <strong>Greg<\/strong>\u2018s implicit trust. <strong>Kathy<\/strong> did not take a salary, rather, <strong>Sterling<\/strong> and <strong>Winters<\/strong> would handle her expenses and had power of attorney. They were relied upon to make investments. <\/p>\n<p>They reportedly led the couple to believe that they \u201cwould never need to worry\u201d about their finances as they were very wealthy.<\/p>\n<p>But the 62-year-old business mogul began to suspect something was amiss when she tried to lend money to her son for a down payment on his home and her managers became \u201cevasive,\u201d claiming it would take six months to liquidate her investments.<\/p>\n<p>The lawsuit states, \u201cThere is no wealth securing their retirement and their children\u2019s futures, as they were led to believe. Instead, in the wake of Defendants\u2019 misconduct, there was staggering debt, misused credit, secret loans, and missing funds.\u201d<\/p>\n<p><strong>Kathy<\/strong> and her husband say they have had to sell their home, lost their home equity and their life insurance policies, and have been left without substantial savings.<\/p>\n<p>\u201cIn short, Defendants treated Plaintiffs as their work horses and piggy banks, all the while scheming to fund their own life style,\u201d the filing adds.<\/p>\n<p>Damages could run as high as $100 million. <\/p>\n<p><strong>Kathy<\/strong>\u2018s attorney <strong>Jill Basinger<\/strong> says they\u2019ve only just begun to find \u201cthe tip of the iceberg\u201d and that <strong>Sterling<\/strong> and <strong>Winters<\/strong> \u201cused their position of trust to enrich themselves while constantly misleading <strong>Kathy<\/strong> about the state of her and her family\u2019s financial health.\u201d<\/p>\n<p>Variety notes that, last October, <strong>Winters<\/strong> shared a social media post claiming kiWW had \u201csputtered and stalled abruptly, creating chaos.\u201d<\/p>\n<p>\u201cThe \u2018I will love you forever\u2019 act went on for decades, as we sipped <strong>Jim Jones<\/strong>-flavored Kool Aid,\u201d he said at the time. \u201cWe should have seen the signs. We did not. We were deceived. It\u2019s easy to be deceived by people you trust.\u201d<\/p>\n<p><strong>Winters<\/strong> then claimed they were seeking a \u201cpeaceful resolution\u201d amid received threatening letters from lawyers.<\/p>\n<p>He asserted that the conflict came from the \u201crefusal of millionaires to cease living like billionaires, preventing others to be paid fairly.\u201d<\/p>\n<p><a href=\"https:\/\/www.justjared.com\/2026\/01\/05\/the-richest-models-in-the-world-ranked-by-net-worth-in-2026\/\" target=\"_blank\" rel=\"noopener\">Find out where <strong>Kathy<\/strong> ranks among the richest models in the world<\/a>.<\/p>\n<\/div>\n<p><script>(function(d, s, id) { var js, fjs = d.getElementsByTagName(s)[0]; if (d.getElementById(id)) return; js = d.createElement(s); js.id = id; js.src = \"\/\/connect.facebook.net\/en_US\/sdk.js#xfbml=1&version=v3.2&appId=145071315902360\"; fjs.parentNode.insertBefore(js, fjs); }(document, 'script', 'facebook-jssdk'));<\/script><br \/>\n<br \/><br \/>\n<br \/><a href=\"https:\/\/www.justjared.com\/2026\/03\/10\/kathy-ireland-is-suing-former-business-managers-claims-decades-of-financial-misconduct-resulting-in-severe-debt\/\" target=\"_blank\" rel=\"noopener\">Source link <\/a><\/p>\n","protected":false},"excerpt":{"rendered":"<p>Kathy Ireland is suing her former business managers over allegations that they swindled millions of dollars from her, leaving her and her family deeply in debt. The former Sports Illustrated swimsuit model launched her brand licensing company kathy ireland Worldwide (kiWW) in 1993, beginning with an exclusive deal with Kmart that included her own clothing [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":227668,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[3],"tags":[],"class_list":{"0":"post-227667","1":"post","2":"type-post","3":"status-publish","4":"format-standard","5":"has-post-thumbnail","7":"category-lifestyle"},"_links":{"self":[{"href":"https:\/\/entertainment.runfyers.com\/index.php\/wp-json\/wp\/v2\/posts\/227667","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/entertainment.runfyers.com\/index.php\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/entertainment.runfyers.com\/index.php\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/entertainment.runfyers.com\/index.php\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/entertainment.runfyers.com\/index.php\/wp-json\/wp\/v2\/comments?post=227667"}],"version-history":[{"count":0,"href":"https:\/\/entertainment.runfyers.com\/index.php\/wp-json\/wp\/v2\/posts\/227667\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/entertainment.runfyers.com\/index.php\/wp-json\/wp\/v2\/media\/227668"}],"wp:attachment":[{"href":"https:\/\/entertainment.runfyers.com\/index.php\/wp-json\/wp\/v2\/media?parent=227667"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/entertainment.runfyers.com\/index.php\/wp-json\/wp\/v2\/categories?post=227667"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/entertainment.runfyers.com\/index.php\/wp-json\/wp\/v2\/tags?post=227667"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}