Charitable Remainder Trusts: How to Sell Appreciated Assets, Defer Tax, and Generate Lifetime Income
A charitable remainder trust lets you contribute appreciated assets, take an immediate charitable deduction, avoid capital gains tax on the sale, and receive income for life or a term of years. It is one of the most powerful tools in estate and tax planning — and one of the most underused.
Charitable remainder trusts occupy a unique position in the tax planning toolkit: they simultaneously serve philanthropic goals, generate current income, and produce significant tax benefits. For the right taxpayer — typically someone with highly appreciated assets, charitable intent, and a need for income — a CRT can accomplish more in a single transaction than almost any other planning technique.
The mechanics are straightforward in concept. The complexity lies in the design choices, the actuarial calculations, and the interaction with the rest of the estate plan.
How a Charitable Remainder Trust Works
A charitable remainder trust is an irrevocable trust that pays income to one or more non-charitable beneficiaries (typically the donor and/or their spouse) for a period of time, after which the remaining trust assets pass to one or more charitable organizations.
The basic transaction works as follows:
- The donor transfers appreciated assets — stock, real estate, a business interest — to the CRT
- The CRT sells the assets without paying capital gains tax (the trust is tax-exempt)
- The trust reinvests the full proceeds and begins making distributions to the income beneficiary
- The donor takes a charitable income tax deduction in the year of contribution equal to the present value of the remainder interest that will eventually pass to charity
- At the end of the trust term (either a fixed number of years or the death of the income beneficiary), the remaining assets pass to the designated charity or charities
The capital gains tax deferral is the central economic benefit. An investor who holds $1,000,000 of stock with a $100,000 basis would owe approximately $171,000 in federal capital gains tax on a direct sale (at the 20% rate plus the 3.8% net investment income tax). By contributing the stock to a CRT instead, the full $1,000,000 is available for reinvestment, and the income stream is based on the undepleted principal.
The Two Types: CRAT and CRUT
There are two primary forms of charitable remainder trust, and the choice between them is one of the most important design decisions.
Charitable Remainder Annuity Trust (CRAT)
A CRAT pays a fixed dollar amount each year — a percentage of the initial fair market value of the contributed assets, calculated once at inception. The payment does not change regardless of how the trust's investments perform.
Minimum payout rate: 5% of initial fair market value
Maximum payout rate: 50% of initial fair market value
Additional contributions: Not permitted after the initial funding
The fixed payment provides certainty for the income beneficiary. If the trust earns more than the payout rate, the excess accumulates inside the trust and ultimately passes to charity. If the trust earns less, the principal is depleted to fund the payments.
The CRAT is appropriate when the donor wants predictable income and does not anticipate making additional contributions to the trust.
Charitable Remainder Unitrust (CRUT)
A CRUT pays a fixed percentage of the trust's fair market value, recalculated annually. If the trust grows, the payments increase. If it declines, the payments decrease.
Minimum payout rate: 5% of annual fair market value
Maximum payout rate: 50% of annual fair market value
Additional contributions: Permitted
The CRUT provides inflation protection — payments grow with the trust's assets — and allows the donor to make additional contributions over time. It is the more commonly used structure for most planning situations.
Several CRUT variations offer additional flexibility:
Net Income CRUT (NICRUT): Pays the lesser of the unitrust amount or the trust's net income. If the trust earns less than the unitrust percentage, the shortfall is not made up in future years.
Net Income with Makeup CRUT (NIMCRUT): Pays the lesser of the unitrust amount or net income, but tracks the shortfall in a "makeup account." In years when the trust earns more than the unitrust percentage, the excess is used to make up prior shortfalls. This structure is particularly useful for donors who want to defer income — by investing in low-yield assets initially and switching to higher-yield assets when income is needed.
Flip CRUT: Starts as a NICRUT or NIMCRUT and "flips" to a standard CRUT upon a triggering event (typically the sale of an illiquid asset or the donor reaching a certain age). This structure is commonly used when the initial contribution is real estate or a business interest that cannot be immediately sold.
The Charitable Deduction
The donor receives a charitable income tax deduction in the year of contribution equal to the present value of the remainder interest — the amount expected to pass to charity at the end of the trust term.
The deduction is calculated using IRS actuarial tables and the Section 7520 rate (a monthly rate published by the IRS equal to 120% of the applicable federal midterm rate). A higher Section 7520 rate produces a larger charitable deduction because the present value of the future charitable remainder is higher when discounted at a higher rate.
The deduction is subject to the standard percentage limitations for charitable contributions:
- 30% of AGI for contributions of appreciated capital gain property to a CRT for the benefit of a public charity
- 20% of AGI for contributions to a CRT for the benefit of a private foundation
- Excess deductions carry forward for up to five years
For a donor with $1,000,000 of appreciated stock and $400,000 of AGI, the 30% limitation means the deduction can be used at a rate of $120,000 per year, with the remainder carried forward. The full deduction is eventually used, but it may take several years.
Taxation of CRT Distributions
CRT distributions are taxed to the income beneficiary under a four-tier ordering system that determines the character of each distribution:
Tier 1 — Ordinary income: Distributions are first characterized as ordinary income to the extent the trust has current or accumulated ordinary income.
Tier 2 — Capital gains: Once ordinary income is exhausted, distributions are characterized as capital gains (long-term before short-term) to the extent the trust has current or accumulated capital gains.
Tier 3 — Other income: Tax-exempt income is distributed next.
Tier 4 — Return of corpus: Only after all income and gains have been distributed are payments treated as a tax-free return of the donor's contribution.
The practical implication is that the capital gains from the initial asset sale do not disappear — they are distributed to the income beneficiary over time as the trust makes payments. The deferral is real, but the gains are eventually taxed. The benefit is that the full pre-tax proceeds are invested and generating returns during the deferral period, and the gains are spread over the trust term rather than recognized in a single year.
The 10% Remainder Requirement
To qualify as a charitable remainder trust, the present value of the remainder interest passing to charity must be at least 10% of the initial fair market value of the contributed assets. This requirement limits how much income can be paid out relative to the trust term and the donor's age.
For a CRAT with a high payout rate or a young donor, the 10% test may not be satisfied — meaning the trust cannot be structured as proposed. The IRS provides tables for calculating whether a proposed CRAT satisfies the test. For CRUTs, the test is generally easier to satisfy because the unitrust payment adjusts with the trust's value.
The 10% test is one reason that CRTs are more commonly used by donors in their 50s and 60s than by younger donors — a longer expected trust term means more payments to the income beneficiary and a smaller remainder for charity, making it harder to satisfy the 10% floor.
CRT as a Retirement Income Strategy
One of the most effective uses of a charitable remainder trust is as a retirement income supplement for donors with highly appreciated assets. The NIMCRUT structure is particularly well-suited to this purpose.
The strategy works as follows: the donor contributes appreciated assets to a NIMCRUT during working years, when income is not needed. The trust invests in growth-oriented, low-yield assets, generating minimal distributable net income. The unitrust amount accumulates in the makeup account. When the donor retires and needs income, the trust shifts to income-producing investments, and the accumulated makeup amount is distributed over several years.
The result is a tax-deferred accumulation vehicle that converts appreciated assets into a retirement income stream — with a charitable deduction in the contribution year and capital gains deferral on the initial sale.
Choosing the Charitable Remainder Beneficiary
The charity named as the remainder beneficiary can be changed in many CRT structures, giving the donor flexibility to direct the ultimate gift as circumstances change. Some donors name a donor-advised fund as the remainder beneficiary, which allows the charitable distribution to be directed to specific operating charities at a later date.
Private foundations can be named as remainder beneficiaries, but the lower AGI limitation (20% vs. 30%) and the additional complexity of private foundation administration make this less common for most donors.
When a CRT Makes Sense
A charitable remainder trust is not appropriate for every taxpayer. The irrevocability of the contribution is the central constraint — once assets are transferred to the CRT, they cannot be recovered. The donor has exchanged the asset for an income stream and a charitable deduction.
The strategy is most compelling when:
- The donor holds highly appreciated assets with a low basis
- The donor has genuine charitable intent — the remainder will eventually go to charity regardless of the tax benefits
- The donor needs or wants income from the assets
- The donor's estate is large enough that the charitable deduction and estate tax reduction are meaningful
- The donor has sufficient other assets to maintain liquidity outside the trust
For donors who meet these criteria, a charitable remainder trust is one of the most tax-efficient transactions available. The combination of capital gains deferral, charitable deduction, and income stream is difficult to replicate through any other single technique.
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Written by
Scott Hatchett
Principal & Owner
Scott Hatchett is the Principal and Owner of Autarky Tax and Accounting. A former US Treasury and IRS agent, he brings insider knowledge of IRS procedures to every client engagement — from proactive tax strategy to audit defense.
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