Content by Jim Duffy

The key advantage lies in the ability to avoid paying capital gains taxes on appreciated assets, such as real estate, stocks, or other investments. A donor can generally claim a charitable deduction for the full fair market value of the property. By contrast, if a donor sells these assets and contributes the sale proceeds, the donor would incur capital gains tax on the appreciation which would decrease the benefit of the deduction to the donor. However, when the property is donated directly to a qualified charity, the donor can bypass this tax liability.

For example, if a donor has stock worth $100,000 that they originally purchased for $50,000 in 2019 and they sold it in 2024 and contributed the $100,000 to charity that same year, the donor would have $50,000 of capital gain and a $100,000 charitable deduction. The donor is subject to a 20% federal capital gains tax (and potentially state tax) on the capital gain of at least $20,000. If we assume that the donor is in the 35% federal income tax bracket, the charitable deduction can save him $35,000 for a net tax benefit of $15,000 ($35,000- $20,000). By contrast, if the donor contributed the stock, they would have no tax but still be entitled to deduct the full $100,000 charitable deduction resulting in tax savings of $35,000.

The contrast is even greater if you compare a gift of cash that was earned as wages or business income because that income is taxed at higher ordinary income tax rates. Assuming the donor is subject to a 35% federal income tax rate, the charitable deduction would simply shelter the tax on the amount of income that is given away ($35,000 tax – $35,000 deduction benefit).

There can be limitations on the deductibility of appreciated property depending on the nature of the charity receiving the donation and whether the value of the gift would exceed certain percentages of the donor’s income, e.g. 30%. Accordingly, advance planning is advisable for significant gifts.

Bottom Line: Donating property to a charity can offer enhanced tax advantages compared to giving cash making it an appealing option for those with appreciated assets.

“I always wondered why somebody didn’t do something about that. Then I realized I was somebody.”– Lily Tomlin

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Photo of James Duffy James Duffy

Jim is a partner in Taft’s Tax practice and practices principally in the areas of federal tax law; tax credit financing; individual, partnership and corporate tax planning; M&A; tax-exempt organizations and general commercial and corporate law.

Jim has been actively practicing in the

Jim is a partner in Taft’s Tax practice and practices principally in the areas of federal tax law; tax credit financing; individual, partnership and corporate tax planning; M&A; tax-exempt organizations and general commercial and corporate law.

Jim has been actively practicing in the area of the New Markets Tax Credits (NMTC) program since its inception in 2001. He has organized community development entities (CDEs) and represented CDEs, borrowers and other parties in structuring and closing numerous NMTC transactions. Jim also advises clients regarding Qualified Opportunity Zone matters.

Jim advises LLCs, partnerships, corporations and individuals in connection with the formation of new companies, mergers and acquisitions, formation of joint ventures, like-kind exchanges, ownership succession planning, and general business operations. These clients are involved in a variety of industries, including banking, venture capital, real estate, construction, consulting and investing.

Jim also advises charitable and non-charitable tax-exempt organizations, including health care entities, schools, religious and civic organizations. In addition to advising management of these organizations with respect to matters pertaining to general operation and maintenance of tax-exempt status, Jim has assisted clients in forming, restructuring and dissolving tax-exempt organizations, as well as forming donor- advised funds.

Prior to joining the firm, Jim worked at the law firm of Lewis Rice and Fingersh in St. Louis, Missouri, where he concentrated his practice in federal and state taxation. He also clerked for the Hon. Robert P. Ruwe of the U.S. Tax Court in Washington, D.C.