In 2017, Milano and her husband Dave Bugliari (pictured) filed a $10 million lawsuit against Milano's former business manager Kenneth Hellie, the equivalent of $12.8 million (£10m) in today's money They accused Hellie of forging signatures on cheques, failing to pay taxes, and encouraging them to make bad investments. These actions apparently left the pair "with millions of dollars in debt and their credit in ruins".

However, Hellie and the couple's ex-accountant both claimed the couple's spending was out of control. According to Hellie's cross-complaint, Milano and Bugliari spent "hundreds of thousands of dollars on a second home in the mountains, private planes, country club membership, a boat, and numerous personal staff." The case was eventually settled but the terms of the agreement were never disclosed.

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