Capital gains taxes

New year, new priorities; advisory service roadblocks; GM sues Frisco; and other highlights from our favorite tax bloggers.

More art than science, financial advisors can face difficulty in determining what constitutes a "substantially identical" security.

While a securities-based loan is more commonly used to buy a fancy house or take a dream vacation, it's also an underused strategy for some affluent investors to pay large tax bills.

Million-dollar baseballs are raining down on fans like pennies from heaven, and the taxman isn't far behind.

Yvon Chouinard described his decision to give away the outdoor apparel-maker as his last-ditch effort to do all he could to protect the planet, but the deal is structured in ways that bring his family tax perks.

Liquidating crypto brings certain challenges, from complicating the underwriting process to possibly triggering significant (and often unexpected) tax gains.

President Joe Biden’s plan to tax unrealized capital gains ran into opposition from key Democratic Senator Joe Manchin, likely dooming it just hours after it was sent to Congress.

The budget calls for a minimum 20% tax rate that would hit both the income and unrealized capital gains of households worth more than $100 million.

The request will show a $1 trillion reduction in deficit spending over the coming decade, generated in part by a new tax targeting billionaires.

The $2.6 billion Miami firm is the largest independent advisor yet to take advantage of the U.S. territory’s incentives.

The bull market has made many wealthy clients overweight in single stocks. Here’s what they can do to diversify their retirement nest eggs and cut taxes.

It's counterintuitive, but basic short selling can boost the after-tax return on an entire retirement portfolio.

The “resident investor” incentive lures wealthy individuals with the promise of legally skirting U.S. income tax.

The ability to deduct the full value of the stock and avoid capital gains taxes is lesser-known by rich investors and many advisors.

Democrats’ tax bill would slash in half the tax benefits of founder stock, but a potential workaround exists.

Many proposals for tax hikes on the wealthy haven't materialized, leaving investors with trusts, gifts or sales that might now seem hasty — or not.

The Internal Revenue Service provided detailed reporting directions Wednesday for certain passthrough entities and taxpayers reporting partnership interests held in connection with the performance of services, often referred to as “carried interest.”

The latest proposal underscores a fierce fight in Congress over ways to pay for Biden's slimmer social-spending agenda.

The 400 wealthiest families slashed their income tax to an average rate of 8.2% from 2010-2018 because of preferential capital gains rates.

Two of the most generous tax loopholes are on the chopping block, the latest surprise in emerging tax increases.