Coming out from under questionable tax shelter
BY BARBARA FLOM
Back in the heyday of irrational exuberance, dot-com IPOs punctuated the business news like the sound of champagne corks popping.
Such an embarrassment of riches seethed around the marketplace that not merely CEOs and business owners but even software programmers and file clerks became independently wealthy. There was only one real problem with all this: taxes. No one wanted to pay them.
In this environment, tax shelter schemes proliferated faster than jackrabbits. An army of accountants, consultants, attorneys, banks and other advisers peddled a range of deals whose common themes were complexity, obfuscation and an element of legerdemain. Income vanished; losses sprang from nothing; tax basis multiplied — and taxes disappeared.
Although these deals weren’t cheap, thousands signed up. Some folks engaged in more than one shelter as they reaped repeated gains from an overheated stock market and sought offsetting losses to avoid paying capital gains taxes.
A lot has changed in the intervening years. The Internal Revenue Service, armed with new disclosure rules, has gone on the offensive: creating a list of suspect transactions, pursuing advisers (both for their own violations and for names of the taxpayers they represented), and opening hundreds of audits.
So, if you bought one of these deals, but the IRS hasn’t knocked on your door yet, what should you do?
Ten ways to tell that the “innovative tax strategy” you were sold is really an illegal tax shelter:
1. You first learned about the strategy when a financial adviser became aware that you were about to recognize an enormous capital gain.
2. Before anyone would divulge the details of this “proprietary” strategy, you (and perhaps your other advisers) had to sign a confidentiality agreement.
3. You heard that only highly sophisticated investors use it, but the strategy was identified by an overly cute name such as “Son of BOSS,” “FLIP/OPIS,” “COBRA” or “BLIPS.”
4. When you signed up, you were advised that the strategy was “bulletproof,” a “slam dunk,” and technically complied with the Internal Revenue Code. But afterward, the lengthy written advice (if you read it) concluded that it was only “more likely than not” that your position would be sustained if challenged.
5. The legal opinions also, if you looked closely, relied heavily on your statements that you were using the strategy for a substantial “business purpose” and planned to make a profit.
6. The strategy involved so many esoteric transactions (short sales, options and derivatives such as swaps and forward contracts) and domestic and offshore entities that you wouldn't have known how to make a profit if your life depended on it. Not to mention that it would have been quite difficult to earn a profit after paying the adviser's hefty fees (typically based on a percentage of your tax savings).
7. Your friends who recommended this adviser laugh nervously when you ask how things are going.
8. Your adviser's voicemail greeting now says that until further notice, he can be reached in his Barbados office. No one answers the phone in Barbados.
9. Your adviser's picture appeared on Page 1 of the Wall Street Journal, in an article outlining how the Internal Revenue Service is assessing substantial taxes, interest and penalties against several hundred taxpayers who engaged in transactions that sound just like yours.
10. Your name is mentioned two paragraphs below your adviser's sketch.
— Barbara Flom
First and simplest, if you value a good night’s sleep, you can file an amended return showing the gain you previously had “sheltered,” pay the tax and interest, and sit back. The IRS will probably send you a 20 percent penalty notice, and you’ll likely be audited once or twice just to make sure you’ve learned your lesson.
It’s painful — but peace of mind can be priceless.
But let’s say you’re not ready to put your head on a chopping block. What else can you do? One possibility is to wait until the IRS makes a “global settlement offer” for your particular shelter, and then decide whether to participate in it. The IRS has already made such offers for Son of BOSS and the Executive Option strategies, and taxpayers have been flocking to take advantage of them.
Just last month, the IRS announced that its Son of BOSS offer led to settlement with some 1,200 taxpayers and brought in receipts of $3.7 billion. The typical offer requires a taxpayer to pay all back taxes and interest, but frequently reduces or waives penalties. Note that these offers take a “carrot-and-stick” approach: The IRS makes it plain that taxpayers who do not take the offer will have to go to court to challenge the assessments.
Still not thrilled?
For those who are itching for a good fight, there are two other possibilities (not mutually exclusive):
uSue the IRS, in either Tax Court or federal district court, to overturn the tax assessment.
uSue the adviser(s) who got you into this mess.
Some taxpayers have sued everyone who had any role in advising them to use these strategies. Litigation being much slower than watching paint dry, most of those cases are still in the earliest stages, and it will be several years before we know whether any taxpayer will recover anything meaningful.
Nevertheless, the law firm of Jenkens & Gilchrist recently finalized an $81.6 million putative global settlement with taxpayers it represented in several types of tax shelter transactions. Although this settlement appears substantial, it shouldn’t raise anyone’s hopes too far. The amount is less than the total fees taxpayers allegedly paid the firm for working on the shelter transactions.
Of course, your best result would be not to have to pay the tax you thought you avoided. Currently, hundreds of taxpayers are attempting to challenge IRS tax assessments on Son of BOSS, “Midco” and numerous other “listed transactions” that the IRS has identified as abusive.
It remains to be seen whether the courts will agree with the IRS that any particular transaction is truly unlawful. In recent years, the IRS has both won and lost some very high-profile cases of this type, and several of those decisions are on appeal.
The IRS has done its best, with disclosure rules and penalties, to discourage shelter activity by altering the cost-benefit analysis of both shelter participants and their advisers. But at the end of the day, whether anything has really changed depends on what you do the next time someone offers to show you how to make income disappear.
Barbara Flom is a principal in the corporate, securities and tax group for the Chicago-based law firm Goldberg, Kohn, Bell, Black, Rosenbloom & Moritz Ltd. She can be reached at barbara.flom@goldbergkohn.com.

