The divorce proceedings led to extensive pieces in the gossip columns. In October 1990 her 63-year-old father died suddenly from a heart attack. The Trumps stood side-by-side at the funeral. Their divorce was settled after that in 1992. Although the settlement remains sealed by the courts, it is rumored that Ivana received $20 million; the $14 million family estate in Connecticut; a $5 million housing allowance; $350,000 annual alimony; all of her jewelry; and 49% of Mar-a-Lago, the family home in Palm Beach, Florida, that also serves as a private club for the Palm Beach elite. Not long after her divorce from Donald, Ivana married Riccardo Mazzucchelli. The marriage was dissolved before two years had elapsed, and she filed a $15 million breach of contract suit against Mazzucchelli for violating the confidentiality clause in their prenuptial agreement. The suit was settled out of court. In 1997, Mazzucchelli sued Ivana and Donald for libel.
In April 2008, Ivana, then 59, married Rossano Rubicondi, then 36. The $3 million wedding for 400 guests was hosted by Donald at his Mar-a-Lago estate. Trump's daughter Ivanka was her maid of honor. On December 1, 2008, Trump confirmed to the Associated Press that she had filed a legal separation agreement three months previously; she has stated in interviews that she and her husband have an on-again/off-again relationship.
CareerSoon after her divorce from Donald Trump, she signed on with the William Morris Agency and developed lines of clothing, fashion jewelry and beauty products that have been sold through television shopping channels. She has also written several books including the novels For Love Alone, Lucy Wilkins and Free to Love as well as a self-help book called The Best is Yet to Come: Coping with Divorce and Enjoying Life Again. In 2001, she penned an advice column for Divorce Magazine. She played a cameo role in the Hollywood film The First Wives Club with the line, "Ladies you've have to be strong and independent. And remember: don't get mad, get everything."
In 2005, she was involved in several proposed condominium projects that ultimately failed, including the never-built Ivana Las Vegas, and the Bentley Bay in Miami, Florida. She was the host of Oxygen Network's reality-dating series Ivana Young Man in 2006. In 2010, she sued a Finnish fashion company, accusing it of selling women's clothing that incorporates her name without permission. In the same year, she took part in the UK's Celebrity Big Brother, finishing seventh.