James Gandolfini's $30 Million Estate Tax Mistake

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In "The Sopranos," the IRS didn't stand a chance against Mafia boss Tony Soprano. But thanks to poor planning, the IRS will be the biggest beneficiary of actor James Gandolfini's estate.

Gandolfini died with an estate worth an estimated $70 million. But in what estate lawyer William Zabel referred to as a "catastrophe" in an interview with the New York Daily News, Gandolfini's will left about 80 percent of his estate unprotected against estate taxes, with rates that will add up to about 55 percent when you consider both the federal and state portions.

What's worse, some well-established estate planning techniques could easily have avoided much of that bill while still achieving most of what Gandolfini was trying to accomplish.

What the Will Said

You can read Gandolfini's will for yourself, but on the whole, it has fairly simple provisions.

After giving $1.6 million to various friends and relatives and making provisions for his personal property and his house and land in Italy, Gandolfini split the remainder of his estate among four people -- 30 percent each to his two sisters, 20 percent to his wife, and 20 percent to his daughter. His son received the proceeds of a life insurance policy that isn't subject to estate tax.

As ordinary as those provisions might sound, Gandolfini's will represents a missed opportunity in estate planning terms. By leaving only 20 percent of his estate to his wife, Gandolfini missed out on what could have been an unlimited deduction for estate tax purposes for gifts made to a surviving spouse.

How to Handle Complex Family Situations

Of course, one complication is that Gandolfini's surviving spouse, Deborah Lin, isn't the mother of his son, Michael. Often in situations involving stepparents and children of previous marriages, parents are reluctant to leave all their money to a surviving spouse, as they want to ensure that their children won't have to rely on their stepparent to provide for them.

However, even in cases involving children of previous marriages, the use of marital trusts can usually take advantage of the marital deduction while still ensuring that children will eventually receive the bulk of the estate.

A typical marital trust will provide for income from trust property to be paid to the spouse, and for the assets that remain after the surviving spouse dies to go to the children or other desired heirs.

You have to be careful in drafting the marital trust so that it qualifies for the marital deduction while still providing protection for your kids, but proper planning can reach a beneficial result that could have cut tens of millions of dollars off Gandolfini's estate-tax bill.

Don't Make a Celebrity Mistake

Gandolfini's estate-planning errors are far from the only tax mistake among celebrities. Some are basic missteps, like Wesley Snipes having failed to file income tax returns and Nicolas Cage having an unpaid seven-figure tax bill outstanding. Lauryn Hill failed to pay taxes for years, and on Monday began serving a three-month sentence for tax evasion.

Moreover, Gandolfini at least had a will. Many celebs who died unexpectedly, including Jimi Hendrix, Amy Winehouse, and Barry White, didn't have valid wills at all, an issue which can raise a host of other complications and unintended results.

So in reviewing your own estate-planning situation, be sure you've taken care of the following issues:
  • Make sure you have a will. Doing so is the best way not only to make sure the right people get your property after your death but also to name someone to take care of minor children in your absence. Without a will, long court battles can ensue, and that will not only create emotional stress but also sap financial strength at a most difficult time.
  • There are a number of other vital documents to have. A living will lets you make your wishes known about life-preserving treatment, while a health-care power-of-attorney will let a loved one act more broadly on your behalf when you're unable to make your own decisions about medical treatment. Similarly, a durable power of attorney will let someone take financial action on your behalf if you're incapacitated, saving a huge amount of complications.
  • Finally, financial planning can be as simple or as complex as you choose to make it. With the federal estate tax exemption currently at $5.25 million, few people have to worry about tax considerations, although some states have estate taxes that kick in at levels as low as $675,000. Make sure to coordinate your will's provisions with your investments, life insurance, and other financial planning to ensure a smooth transition if something happens to you.
No one likes to contemplate their own death. But the expensive lesson that the IRS is about to teach the Gandolfini family is one that you don't have to learn the hard way, as long as you take some easy steps now to avoid a big IRS bill later.

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James Gandolfini's $30 Million Estate Tax Mistake
Hill, the former Fugee and solo artist behind The Miseducation of Lauryn Hill -- one of the most highly-praised albums of the 1990s -- pleaded guilty in 2012 to charges that she hadn't paid federal income taxes for three years (2005-2007), during which she made more than $1.8 million. On May 6, 2013, Hill was sentenced to three months in prison.  Hill explained herself in a blog post, saying she had gone "underground" "in order to build a community of people, like-minded in their desire for freedom and the right to pursue their goals and lives without being manipulated and controlled by a media protected military industrial complex with a completely different agenda."

This project also entailed ignoring state taxes: A New Jersey court found Hill responsible for $446,386 in unpaid state taxes.
In April 2012, The Detroit News reported that skiing star Vonn and her estranged husband Thomas owed $1,705,437 in taxes from 2010, the year Vonn took Olympic gold in downhill at Vancouver. Vonn sounded genuinely surprised and moved quickly to settle the debt. "This is an important lesson for me," she said in a Facebook post. "Not being in control of my finances and relying on someone else who you believed had your best interest at heart was a mistake" -- an allusion to Vonn's husband, according to The Christian Post -- "and one I will not make twice."

Vonn is currently dating Tiger Woods, so everything should be fine now.

The star of The Flintstones in Viva Rock Vegas (2000) and Celebrity Big Brother 2010 was arrested in December 2012 and charged with failing to pay more than $350,000 in New York state income taxes; Baldwin apparently failed to file in 2008, 2009 and 2010.


By pleading guilty to one count of repeated failure to file -- a class "E" felony -- Baldwin avoided prison time. He has already paid the state $100,000 in restitution and has agreed to shell out an additional $300,000 before his sentencing on July 19, 2013.

Ja was sentenced to two years in prison on an illegal gun charge in late 2010, and in July 2011 he received an additional 28 month sentence for having failed to pay taxes on $3 million between 2004 and 2006. The judge allowed him to serve his terms concurrently; he is set to be released on July 28.

Ja denied intentional wrongdoing on the tax evasion front. "I in no way attempted to deceive the government or do anything illegal," he said in court, according to BET. "I was a young man who made a lot of money .... I didn't know how to deal with these finances, and I didn't have people to guide me, so I made mistakes."

It's not the worst thing he's ever done, but O.J. Simpson has been a less-than-diligent taxpayer. The IRS first filed a lien against the former running back in 2011, saying Simpson hadn't paid taxes since 2007 and owed the government almost $180,000. A second lien was filed early in 2013, covering $17,015.99 in income taxes for 2011.

Though he was acquitted of double-murder in 1995, Simpson has been in prison for armed robbery since late 2008.
Lohan got good news at the end of last year, when the IRS released her from a tax lien after seizing her bank accounts. Lohan was able to pay off her 2009 tax bill -- $93,701.57 -- after Charlie Sheen cut her a check for $100,000. Other debts remain, from 2010 and 2011, but Lohan's business manager is said to be working to settle the six-figure balance.
There was a time when Gosselin had it all: a wife, twins, sextuplets, and his own reality TV show -- a 21st century American dream. Then it all unraveled. I don't know quite how, because I've never seen Jon and Kate Plus 8, but it may involve his alleged affair with the daughter of his wife's plastic surgeon, the dropping of his name from the title of the show, and a threat to prosecute TLC camera crews if they entered his house. Gosselin's child support payments are now reportedly in arrears for $3,557.06, and the Pennsylvania Department of Revenue has filed a $39,000 tax lien against him.
The Super Bowl champion wide receiver had a federal tax lien filed against him in 2012. The IRS said Burress and his wife didn't pay income taxes in 2007 and 2009, leaving an outstanding bill of $98,064.76. Burress was also the target of a New York State lien, alleging he owed $59,241 in unpaid income tax for 2007.

Burress's standout career was interrupted in 2008 by an accidental self-inflicted gunshot wound to the right thigh. According to the AP, "Burress has a history of being sued over debts a millionaire professional athlete seemingly could have paid."
The Bronx-born rapper faces up to two years in prison, as well as a fine of $200,000 plus IRS penalties and court costs, after pleading guilty to failing to file tax returns in 2007 and 2008, when he made nearly $3 million. Joe will be sentenced in April.

According to the AP, "His sentencing will take into consideration the government's initial allegation that he failed to pay income taxes for years 2007 through 2010," costing the Treasury $718,038. When the judge asked him if he understood the charges he was facing, Fat Joe replied, "I super-understand it."
We're not here to talk about anything else R. Kelly has ever done or been accused of doing. Not composing and performing the anthemic theme song to a cinematic teamup of Bugs Bunny and Michael Jordan, nor turning a series of weirdly amusing soap operettas into an endlessly iterating urban saga. All that matters, for our purposes, is that R. Kelly owed money on taxes from 2005 to 2010, for a total of $4,848,072.71, according to an IRS filing. Maybe his accountant was trapped in the closet.
It's been a weird descent for Flavor Flav, from hype man for legendary hip hop group Public Enemy to serial star of VH1 reality shows. Weird but lucrative, since Flav allegedly owes $906,250.56 in back taxes from 2004-2006, according to TMZ.
Sometimes you can tell a story in numbers. Five Grammys, 100 million records, 30-plus singles, $1,000 bank account, $10.2 million owed to the IRS and the state of California. This is the tale of singer and "psychic friend" Dionne Warwick, who declared bankruptcy last week. Warwick, who still sings live, blamed her troubles on "several consecutive years of negligent and gross financial mismanagement." Here's hoping she turns things around.
There's more to Federline than backup dancing and a two-year marriage to Britney Spears: There's also a $57,615 tax lien filed by the IRS for unpaid taxes in 2009 and 2010.
The former Commodore was alerted in April 2012 to an IRS tax lien to the tune of $1.1 million. He responded with characteristic smoothness: "I was recently made aware of the situation by my new team, and it's being handled immediately." It was him they were looking for.
According to Australian authorities, the star of the "Crocodile Dundee" films and his business partner owed a whopping $150 million in taxes. The allegations came as part of a 2004 fraud investigation called Operation Wickenby; the government said Hogan and others used offshore tax havens. The actor was even briefly prevented from leaving Australia after he returned in 2010 for his mother's funeral. Accounting Today reported in May 2012 that the issue was resolved on a "without admission" basis.
You may know comedian Katt Williams from Nick Cannon's "Wild 'n Out," ABC's "My Wife and Kids," or Comedy Central's "Roast of Flavor Flav." The IRS knows him as a delinquent taxpayer against whom they have filed two liens -- one in 2012 for failure to pay $3.2 million for 2008 and $829,352 for 2009, and another in 2010 for $284,000.

Williams's alleged reluctance to pony up for Uncle Sam stands in contrast with his professed love for his country. After telling a Mexican heckler to "get the (expletive) over there!" -- meaning Mexico -- Williams explained, "I don't think I need to apologize for being pro-America." The heckler, he said, had directed an obscenity at the United States.
Weezy, the man with the most entries on the Billboard Hot 100 chart -- 109 tracks, more than Elvis had (although Wayne was a guest on most of them) -- has had a lot of trouble paying his taxes. Accounting Today reports three separate liens against him: $1.13 million in December 2010 for the years 2004, 2005, and 2007; $5.6 million in 2011 for the years 2008 and 2009; and $7.72 million, paid by Wayne at the end of last year.

Wayne recently wound up in the hospital after what was either an attack of epilepsy or a nasty reaction to the codeine cough syrup concoction known as purple drank. In 2010, he served eight months in Rikers Island for a gun charge.
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