TV Mob Boss’ Timing no Match for “The Boss”

Like millions of others, I was heartbroken over the recent death of James Gandolfini, whose portrayal of one of the most complex TV characters of all time – New Jersey mob capo Tony Soprano – made the eponymous HBO series “The Sopranos” a Sunday night must-watch at Chez Carlino.

The burly Gandolfini injected equal parts ruthlessness and sympathy into the Tony Soprano figure, and elevated him from character actor status into a global star.

But sadly, once the obits and tributes stopped, I read where the biggest beneficiary of Gandolfini’s sudden death at age 51 - following a Bacchanal-style meal and binge drinking at a Rome hotel - appears not to be his young children or widow, but Uncle Sam.

Eighty percent of his estate, valued at roughly $70 million, was earmarked to his nine-month old daughter and his sisters. But more than half (55 percent to be exact) will be subject to the “death tax” – or $30 million thereabouts, going to the IRS. The remaining 20 percent was designated to go to his widow.

But Gandolfini’s will stipulated that the shares to his widow would be paid out after any and all tax bills are settled. So to put that in dollar amounts, she stands to receive $8 million. Some 20 percent of the pre-tax amount would have come to around $14 million.

But in death as in life, timing is everything.

Case in point.  Three years ago we lost another larger-than-life “Boss,” George Steinbrenner, the principal owner of the New York Yankees, who passed away in late 2010 at the age of 80. But almost like he knew the end was near, Steinbrenner timed his last out perfectly, expiring just a few months before the federal estate tax was to be resurrected at the aforementioned 55 percent.

That saved his wife and four children a tax bill of more than $500 million, as his net worth at the time as estimated by Forbes, was just over $1 billion.

But it’s not all bad news for Gandolfini’s beneficiaries. Reportedly, he bequeathed a $7 million life insurance policy to his 13-year old son as well as separate trusts for the boy and his wife.

But clearly, Gandolfini did not envision this nightmare tax scenario during his dubious estate planning.

Tony Soprano would not have left Carmela, A.J. and Meadow wanting for anything had any of the various assassination plots in the series against him ultimately succeeded.

But unlike a popular TV series, when it comes to will and estate planning, sadly there’s no such thing as a rerun.