Capital gains taxes

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

There’s no telling where the vast fortunes hide on tree-softened Phillips Avenue here in Sioux Falls.

Joan Crain’s job is to guide the wealthy through complicated financial decisions where mistakes can cost millions of dollars. That task is proving particularly tricky now thanks to Joe Biden’s proposed tax plan and the lack of clarity over what the Democrats will pass.

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

The effort to appeal to centrist Democrats fails to take into account gaping loopholes lawmakers must close if they plan to fund an ambitious spending proposal.

While Biden isn’t getting some of his proposed tax increases on the wealthy, some surprising new hikes may be in the works.

Fighting among Democratic lawmakers over proposed hikes in individual and capital gains taxes is intensifying, creating more questions and opportunities for advisors.

Using private placement life insurance to avoid taxes is getting more popular, some financial advisors say.

Will the giant tax incentive thrive as a tool to defer, minimize and eliminate capital gains tax?

A Treasury Department spokesperson gave an answer that provides clarity for advisors with affluent clients.

The $1 million threshold at which the 23.8% capital gains rate would nearly double has sparked questions — and a strategy for some well-paid professionals.

Most advisors don’t know about the tax benefit for qualified small business stock, which can put millions of dollars tax-free into an entrepreneur-client’s bank account.

Many indexes rebalance quarterly or twice a year, so they’re slow to reflect stocks whose wild swings no longer reflect an investor’s goals.

Securities-based lending is up sharply as wealthy investors leverage gains in their stock portfolios into low-interest loans for pricey purchases.

Trusts aren’t just for the .01%, as some advisors sell mass affluent and high-net-worth clients on their tax benefits.