Can a CRT be leveraged to create matching challenges for public donors?

Charitable Remainder Trusts (CRTs) present a surprisingly effective, yet often overlooked, mechanism for stimulating public donations through matching challenges. While traditionally viewed as a sophisticated estate planning tool for high-net-worth individuals, the structure of a CRT allows a charity to essentially “pre-fund” a matching gift campaign, incentivizing broader participation from the public. This is accomplished by utilizing a portion of the CRT’s assets to meet the match, effectively amplifying the impact of smaller donations. The key lies in carefully structuring the CRT and the associated matching challenge to align with both the donor’s financial goals and the charity’s fundraising objectives. Many donors seek tax advantages while supporting causes they believe in, and a CRT-funded match provides a win-win scenario for everyone involved. This strategy requires careful planning and legal expertise, but the potential for increased donations is significant.

What are the tax benefits of using a CRT for matching gifts?

The tax advantages associated with CRTs are substantial, which makes them particularly attractive for funding matching gift challenges. Donors contributing assets to a CRT, like appreciated stock or real estate, can generally avoid capital gains taxes on the transferred assets, while simultaneously receiving an immediate income tax deduction for the present value of the remainder interest that will ultimately benefit the charity. According to the National Philanthropic Trust, approximately $39.09 billion was distributed by donor-advised funds and CRTs in 2022. This tax benefit frees up more capital for the matching challenge. The charity then receives a stream of income from the CRT, which can be earmarked specifically for matching donations during a defined campaign period. This effectively “leverages” the initial CRT contribution to generate a much larger overall fundraising result. Furthermore, the CRT provides a predictable and sustainable funding source, reducing the charity’s reliance on unpredictable annual fundraising efforts.

How does a CRT compare to a donor-advised fund for matching gifts?

Both CRTs and donor-advised funds (DAFs) can be used to fund matching gift challenges, but they operate quite differently. DAFs are simpler to establish and administer, offering greater flexibility in grantmaking. However, they do not offer the same level of income tax deduction as a CRT, nor do they avoid capital gains taxes on appreciated assets. A CRT, on the other hand, is more complex and requires ongoing administration, but it offers potentially larger tax benefits and allows the donor to receive income for life or a specified term. “About 85% of charitable giving in the U.S. comes from individuals, and increasingly, those individuals are looking for ways to maximize their philanthropic impact,” states a recent report by Bank of America. The choice between a CRT and a DAF depends on the donor’s individual circumstances and financial goals. For instance, someone seeking both income and a significant tax deduction might prefer a CRT, while someone prioritizing simplicity and flexibility might opt for a DAF.

What went wrong when the Miller family tried a matching challenge without a CRT?

I recall working with the Miller family, who were eager to support the local children’s hospital. They announced a matching challenge – promising to match every dollar donated up to $50,000. Initially, donations poured in, fueled by the excitement of the match. However, they hadn’t fully accounted for the logistics. They intended to fund the match from their personal savings, but a sudden, unexpected business downturn left them struggling to meet their commitment. As a result, they could only fulfill about 60% of the promised match, which understandably angered some donors. The hospital had to scramble to cover the shortfall, damaging its reputation and creating significant internal stress. It was a painful lesson about the importance of having a secure and dedicated funding source for any matching challenge. The impact went beyond dollars and cents; it eroded trust and strained relationships with supporters.

How did the Thompson’s CRT-funded challenge restore donor confidence?

Fast forward to the Thompson family. Knowing the Millers’ experience, they approached me with a different plan. They established a CRT, contributing a substantial portfolio of appreciated stock. This not only avoided capital gains taxes but also created a steady stream of income earmarked specifically for a $100,000 matching challenge for the local animal shelter. The campaign launched smoothly. Donations steadily increased, knowing the full match was guaranteed. The shelter exceeded its fundraising goal by 20%, and donor confidence soared. The Thompsons’ foresight transformed a simple matching challenge into a powerful statement of commitment. Their approach demonstrated that a carefully structured CRT could unlock substantial philanthropic potential. It wasn’t just about the money; it was about building lasting relationships with donors and strengthening the community. In fact, several donors indicated they would be establishing CRTs themselves, inspired by the Thompson’s generosity.


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