The divorce was final in 2014. The next year, Smith married Hope Dworacyzk, Playboy’s 2010 Playmate of the Year and a “Celebrity Apprentice” participant until Donald Trump fired her. For the wedding, at a five-star hotel along Italy’s Amalfi Coast, the couple’s seven-month-old son floated down the aisle atop an artificial cloud. John Legend and Seal entertained the crowd.
Smith also sold about one-third of Vista to Dyal Capital Partners beginning that year for an undisclosed amount.
A criminal inquiry soon emerged. In 2016, near the end of the Obama administration, prosecutors sent out subpoenas from a San Francisco grand jury to witnesses, people familiar with the matter said. The investigation is being conducted by the Justice Department’s Tax Division and the U.S. attorney’s office for the Northern District of California. A veteran Tax Division prosecutor, Corey Smith, is working on both the Smith and Brockman cases, the people said.
Among other matters, investigators have focused on the winding down of Smith’s first fund in 2014, the year of his divorce, the people said. Two offshore entities began transferring $247 million in proceeds from Vista Equity Fund II to Fund II Foundation, the charity where Smith is president.
One of those offshore entities was St. Kitts- and Nevis-based Flash Holdings LLC, tax filings show. At issue is who beneficially owned Flash, the people said. Also under scrutiny is an unusual agreement driving the transfer to the foundation, the people added. The foundation has said a promise was made in 2000 by Vista’s first fund to transfer its remaining assets to charity after covering its obligations to its limited partner. It’s unclear whether there’s a written agreement from the fund’s inception outlining the pledge.
None of this artful financial work could have been achieved without advisers and lawyers. Prosecutors found at least one and applied pressure a couple of years ago.
Evatt Tamine, an Australian lawyer, lived in Bermuda and worked for various offshore trusts and companies. Tamine was a director of St. John’s Trust Company, which oversaw Brockman’s trust. His wife, Sophie Tod, also an attorney, became a director of the foundation led by Smith.
The Tamine family was in the U.K. when Bermuda police and IRS agents raided their home in September 2018 at the request of the U.S. Justice Department. A housekeeper met the agents, who spent hours seizing documents and encrypted electronic devices, according to a person who described the scene. Prosecutors later raided a storage locker, court records show.
Ultimately, Tamine received immunity to help U.S. prosecutors unravel the financial matters, according to court records. He has testified three times before the grand jury in San Francisco and has provided emails and other documents to prosecutors, according to a person familiar with the matter.
Court actions followed in Bermuda and the U.K. over which of the lawyer’s documents were protected by privilege, whether Tamine stole money and who should be appointed trustees.