Tony Soprano may have been an expert at hiding his money from the feds, but actor James Gandolfini, the recently deceased actor who portrayed the fictional New Jersey mob boss on TV, apparently was not.

Moreover, advisors say that wealthy families can take some lessons from the mistakes the award-winning actor made in mapping out his estate plan.

Federal and state tax collectors will take more than $30 million of Gandolfini’s estimated $70 million estate, according to published reports. Gandolfini, who starred in the acclaimed HBO series The Sopranos from 1999 to 2007, died of a heart attack while vacationing in Rome last month at age 51. Estate attorney William Zabel, who reviewed Gandolfini’s will for the New York Daily News, called it “a disaster.”

Wealthy individuals and families looking to protect their estates from the heavy tax burden Gandolfini’s is facing should employ the right estate planning strategies early and update those plans as their circumstances change, experts say.

“Gandolfini passing away at age 51 reminds everyone that we’re not immortal and everybody should make sure they stay on top of their estate planning documents,” said Michael A. James, managing director of family wealth at Glenmede in Philadelphia, who recommends clients review their estate plans annually.

“One of the biggest challenges of estate planning is to get people motivated to do it,” said Stephen Breitstone, head of the tax law group and an estate strategist at Meltzer, Lippe, Goldstein & Breitstone in Mineola, N.Y. “If they don’t think they’re going to die, they’re going to put it off for another day.”

Trust Solutions

One of the most effective ways to protect estate assets is through the establishment of various trust vehicles. Under current U.S. estate and gift tax law, an individual is permitted to transfer $5.25 million into an irrevocable trust free of gift tax; married couples may put in $10.5 million.

While married couples may transfer unlimited amounts to each other outright or in trust without paying any federal estate or gift tax (as long as the recipient is a U.S. citizen), a marital trust may be right for many wealthy couples, according to estate planners. When the first spouse dies, estate assets are placed in the marital trust. The surviving spouse is provided for by the income the trust generates, but does not have access to assets intended for children or other heirs. This is especially important when children from different marriages are inheriting.

Establishing an irrevocable life insurance trust provides powerful estate tax advantages for wealthy individuals and families, according to Gary S. Wolfe, who leads the Los Angeles-based network of independent attorneys and consultants at Wolfe Law Group.

“If you spend $5 million for a life insurance premium and you get a $30 million death benefit, you just went six to one on your money and could have paid the entire estate tax out of that money,” Wolfe said.

Creating an offshore irrevocable life insurance trust delivers even greater tax advantages and more flexibility, according to Wolfe. For U.S. taxpayers, Puerto Rico offers the best of both worlds. The island is a U.S. territory and considered part of the U.S. for many practical purposes, but with the design and investment flexibility typically found in other offshore financial centers.

“The reason to do it offshore is that there is no restricted menu of investments,” said David E. Richardson, CEO of Mid-Ocean Consulting in Nassau, Bahamas. “You can invest the cash-value premiums in any investments you want, including hedge funds. Onshore, you’re restricted to a menu of investments that is determined by state insurance regulations, which often limit you to mutual funds or bond funds and which often underperform other investments.”

The strategy requires that the investments of U.S. taxpayers be held by a Puerto Rico-issued life insurance policy. Doing so will streamline tax reporting for U.S. citizens by eliminating the need to file a Foreign Bank and Financial Account (FBAR) disclosure form, which is required for investments in other offshore locations, and minimizing the likelihood of an Internal Revenue Service audit, according to Richardson.

Estate Modeling