As the year comes to a close, both philanthropy and taxes often come to the forefront. There are ways to combine your year-end charitable giving with “harvesting” losses within your portfolio, to maximize tax efficiency and boost your donating power.

Here’s how to combine tax-smart strategies – tax-loss harvesting declines in the value of holdings in your portfolio – with gifting appreciated securities held long-term. Together, they let you give even more to your favorite charities tax-efficiently, and lower your tax bill, too.

Tax-loss harvest to lower capital gains taxes

You may be familiar with the practice of tax-loss harvesting to reduce your tax burden. That’s the process of selling a stock that’s declined below its purchase price, realizing a loss and then using that loss to offset capital gains in other parts of your portfolio. (The loss must be realized; it cannot be an unrealized loss on paper alone.)

Two points to keep in mind when harvesting tax losses:

• Selling depreciated stock needn’t disrupt your long-term investing goals or your asset allocation. When selling a stock for tax purposes, you can preserve your portfolio’s objectives and maintain your desired portfolio balance by buying another stock with similar characteristics.
• Be mindful not to violate the wash sale rule. This IRS statute states that you can’t claim the loss if you buy the same or substantially identical stock or securities 30 days before – or after – the loss sale trade date. So choose your replacement stock wisely, and time the purchase correctly.¹

Over time, tax-loss harvesting can create significant tax savings. For example, if you owned a $10 million equity portfolio, realizing a tax benefit of 1.5% in a single year could result in potential savings of about $150,000.

By intentionally realizing losses to help minimize your tax bill, tax-loss harvesting also lowers your portfolio’s overall cost basis.²

This gradual decrease of the portfolio’s cost basis over time, combined with markets’ historically upward direction, can leave your portfolio holding many highly appreciated stocks (with large, unrealized gains). That would limit your opportunities for further loss harvesting.

Which brings us to the topic of charitable giving…

Consider donating (some) unrealized gains

If charitable giving is part of your wealth objectives, you can boost your philanthropic giving even further, and reap additional tax benefits, by combining tax-loss harvesting and charitable giving – i.e. donating low-basis (bought low and now highly appreciated) securities with a long-term holding period – gifting them, for example, to a donor-advised fund (DAF).

If you itemize deductions on your tax return instead of taking the standard deduction, gifting qualified appreciated stock that has been held for over a year³ to a DAF, for example, may complement tax-loss harvesting and extend your tax benefits, as many donations are, of course, tax deductible.⁴

This way, the charity benefits – and you don’t pay those taxes.

Let’s break down the advantages of donating appreciated securities to benefit both your tax bill and your favorite charity:

• You can deduct the shares’ full market value. Donating stock you have held for over a year⁵ to charity generally allows you to deduct the security’s full fair market value (subject to limitations based on adjusted gross income). You can use the tax deduction in the tax year in which the charitable gift is made, with any excess charitable deductions carried forward for use in five subsequent years.
• You may eliminate capital gains tax on the appreciation. There’s a big difference between donating appreciated stock and selling the stock and donating the proceeds. The capital gains tax you’d incur by selling the stock can potentially be eliminated because charities are typically exempt from paying these taxes. This is likely to increase your charitable contribution’s value by over 20%, benefiting both you and the charity.

The ins and outs of charitably giving appreciated stock

You’ll want to bear in mind a few details if you’re considering charitably giving appreciated stock:

• For the stock to be qualified, you must have held it for over a year⁶
• You must be a U.S. taxpayer who itemizes deductions on your tax return
• If you have various lots of the same stock, it’s possible to choose, and give to charity, the lot with the lowest basis (the highest gainer)

A donor-advised fund might make sense

DAFs are charitable giving vehicles that are easily established, simple to use, cost-effective and tax-efficient. You can receive an immediate itemized tax deduction for your contribution to a DAF, while having time to strategically identify the charities and causes that you’d like to donate to.

After donating appreciated stock to a DAF, you can replenish your portfolio with cash to purchase the same or similar stock. This would create fresh lots with higher cost bases, complementing the tax benefit of charitable gifting. That’s because fresh lots are more likely to go into loss territory and qualify for capturing tax losses, extending the runway for tax benefits in the future.

Combining tax-loss harvesting with charitable giving can provide significant tax benefits while helping you make a meaningful impact on the causes you care about.

Contact us for tax efficient gifting this season

Don't let these powerful strategies go untapped. Take the next step toward optimizing your investment portfolio and achieving your financial and philanthropic goals. Your J.P. Morgan advisor can help tailor a plan that aligns with your distinct needs and aspirations.

Your journey to smarter giving and greater tax efficiency starts now.