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7 Charitable Giving Missteps and Higher Taxes on Capital Gains

7 Charitable Giving Missteps and Higher Taxes on Capital Gains

| May 12, 2021

Individuals, foundations, bequests, and corporations gave an estimated $449.6 billion to U.S. charities in 2019, according to findings in [[ Giving USA 2020: The Annual Report on Philanthropy for the Year 2019]].

Individuals accounted for an estimated $309.7 billion, up 4.7% in 2019 versus the prior year. Foundations added an estimated $75.7 billion, while another $43.2 billion was given by bequest.

We tend to think about charitable donations around the holidays. It’s year-end and your gift to a charity may be sparked not only by your desire to help others, but by tax planning strategies.

The standard deduction is much larger today thanks to 2018’s tax reform, which reduced the incentive to give for some folks. Gifts to a charity can only reduce your tax bill if you itemize when filing. If you were unable to itemize, 2020 came with a small concession. You could deduct up to [[ $300 of cash donations]] without having to itemize.

But let’s not forget that your gifts will not qualify for a tax deduction unless they are received by a tax-exempt organization, as defined by section 501(c)(3) of the Internal Revenue Code. For example, making donations to a personal fundraiser through [[ GoFundMe]] is growing increasingly common, but they are not tax deductible.

While ensuring your gift is tax deductible is one challenge, there are others you’ll need to navigate, too.

Let’s review seven potential potholes to avoid when it comes to charitable giving.

  1. Spreading limited dollars over too many causes. I call this “trying to butter everyone’s bread.” There are plenty of worthy charities. However, might it be a good idea to concentrate your limited resources on causes you are most passionate about?

Here are some ideas. You might consider educational charities, culture and the arts, health and organizations that look for treatments and cures for diseases, charities that benefit animals or the environment, your church or place of worship, human services, international relief, or organizations that support the poor in your community.

The choices are almost limitless. Your resources are not.

  1. Getting the best return. You’ve found charities that meet your criteria. For many, we want the best return on our dollar. We want our cash to be spent and invested wisely, not frittered away by large administrative costs.

According to CharityWatch, “Ask how much of your donation goes for general administration and fundraising expenses and how much is left for the program services you want to support. Most highly efficient charities spend 75% or more on programs.

“Keep in mind that newer groups and those that are working on less popular issues may find it necessary to spend a greater percentage on fundraising and administrative costs than well-established, popular groups.”

According to [[ Smart Asset]], which reviewed a report by the Tampa Bay Times and The Center for Investigative Reporting, 50 charities collected more than $1.35 billion in donations. Yet, $970 million went not to worthy recipients, but to the people who collected the money.

You desire to support your cause, not enrich the fundraisers.

A small effort on your part, i.e., “kicking the tires” of the charity, will go a long way. There are several charity watchdogs you can find online. Do your homework. You may find your decision reinforced by what you find. Or you may decide to steer clear of a particular organization based on your research.

  1. Skip the middleman. Give directly to the charity and avoid solicitors. The middleman gets paid to raise funds. That’s a haircut on your donation you will want to avoid.


  1. Steer clear of emotional appeals. This is tricky and difficult. We want to help. We feel good about ourselves when we share our blessings with others who are less fortunate. It’s part of who we are. Emotional appeals pull at our heartstrings. No one, including myself, is immune to what appear to be worthy charities. 

Just be careful. You may want to concentrate on causes that have special meaning to you.

Furthermore, be careful about what might be called the flavor of the month. For instance, when a disaster occurs, there are reputable outfits we are all familiar with.

Sadly, fraudsters can also play on our desire to help. Donate here and little if any money will make its way to those suffering from a natural disaster. Instead, your funds may simply line the pockets of scammers.


  1. Why wait until the last minute. Many nonprofits get a big chunk of cash at year-end. If possible, you can set up monthly payments that help even out the cash flow of these organizations, making it easier on their budgets—and your finances.


  1. Rethink the small donation. Ten dollars is ten dollars, and plenty of ten dollar donations will add up, but processing costs for the charity is high. Besides, if you give once, you’ll probably be inundated by requests that raise a nonprofit’s costs, diluting the impact of your one-time gift.


  1. Failure to develop a strategy. As I’ve said, we are tempted to respond when we hear a well-crafted message. Sometimes, it is a worthy cause. Our desire to help is admirable, and it speaks volumes about who we are, but be careful about exhausting limited finances and reducing donations to causes you care about the most.

Will you be paying higher taxes on your capital gains?

The short answer is probably “No.” The longer answer is, “I don’t know” because tax hikes proposed by the president may or may not be enacted into law by Congress.

Last month, President Joe Biden unveiled [[ The American Families Plan]], which among other things, proposes to raise capital gains taxes on long-term capital gains—on the sale of assets held more than one year—for households earning more than $1 million in income.

This won’t affect most people, at least directly. I don’t plan on diving into the economics behind the proposal. But if the plan becomes law, let’s look at ways we can use tax planning strategies to avoid or lessen the impact.

Thanks to a stronger economy, the successful rollout of the vaccines, very low interest rates, and more, stocks have rallied sharply over the last year. You have benefited, but the sale of an asset could create a tax liability, depending on your tax bracket and how long you’ve held the asset.

Today, the [[ maximum long-term rate on capital gains is 20%]] plus [[ the 3.8% net investment income (NNI) tax on certain income]].

But if you earn more than $1 million per year, listen up. Your rate may go much higher.

Currently, ordinary income is taxed no higher than 37.0%. That could rise to 39.6% if the president’s plan is approved. If you earn over $1 million, you may pay that 39.6% rate on the sale of assets held over one year plus the 3.8% NII tax.

It’s a substantial increase in taxes for the wealthiest Americans.

How might we lessen the impact, assuming we see a big increase in the capital gains rate?

  1. If a higher rate is not made retroactive, we can consider recognizing profits in tax year 2021, thus avoiding the new rate. Further, we step up the cost basis.


  1. Another way to sidestep the tax is to simply avoid large asset sales in taxable accounts, assuming there isn’t a compelling reason to do so. The only constant in tax law is change, and a future Congress and president could adjust the rates again.

However, there is an important caveat: the time-honored tradition of passing on assets to heirs without paying taxes could be in jeopardy, which most of you know as the stepped-up basis at death.  In his proposal, the president wants to [[ trigger taxes on unrealized gains passed to heirs]]. This would occur after a $1 million exemption.

  1. We can also strategically time the sale of assets, making sure we do not pass the $1 million limit on income. That would ensure the maximum federal rate paid would remain at 20% plus the 3.8% NII tax. It’s a far cry from 43.4%.

In a perfect world, we would not allow investment planning to be affected by tax planning. But tax laws and tax planning do affect investment planning.

Biden’s proposals are a long way from being enacted into law. They may be modified in Congress before any bill reaches his desk and is signed into law. Our team will be closely monitoring the situation. We can become more proactive when we have a better idea how everything will shake out.

As always, we encourage you to consult with your tax advisor before implementing any tax strategies.

Table 1: Key Index Returns




Dow Jones Industrial Average



NASDAQ Composite



S&P 500 Index



Russell 2000 Index



MSCI World ex-USA*



MSCI Emerging Markets*



Bloomberg Barclays US Aggregate Bond Total Return



Source:, Bloomberg, MarketWatch

MTD: returns: Mar 31, 2021—Apr 30, 2021

YTD returns: Dec 31, 2020—Apr 30, 2021

*in US dollars


I trust you’ve found this review to be educational and informative.

If you have any questions or would like to discuss any matters, please feel free to give me a call.