Billionaire Tax Proposal Sets Ultra-Rich on the Hunt for Ways to Avoid It

Democrats’ proposal for a tax on billionaires is already spurring questions about how the sweeping new levy would be implemented and how America’s wealthiest -- and their sophisticated advisers -- can get around it.

The plan attempts to zero in on a narrow slice of the super-rich -- those with at least $1 billion in assets or incomes of $100 million for three consecutive years. Anyone in that category would be forced to pay an annual tax on any unrealized gains on publicly traded assets like stocks. For private assets, which are far more difficult to value, the Internal Revenue Service would take a more hands-off approach, requiring billionaires pay an extra tax when the holdings are sold.

Advocates of the tax, including its sponsor, Senate Finance Committee Chairman Ron Wyden, say it’s a way to raise revenue while leveling the playing field between the middle class, which pays taxes every year on their salaries, and the very wealthy, who can use a variety of strategies to defer tax bills, sometimes indefinitely. Critics of the levy argue it would too difficult to implement, may be held unconstitutional by the Supreme Court and, according to billionaire hedge fund manager Leon Cooperman, represents a deplorable example of “attacking wealthy people.”

Democrats’ biggest challenge in designing such a tax may be devising ways to make sure that the richest Americans actually end up paying it. The legislation -- which was unveiled Wednesday but has been under consideration by Wyden and his team for a couple of years -- includes provisions aimed at blocking strategies, such as trusts and insurance products, that advisers to the top 0.0001% were already thinking about deploying.