Navigating Estate Planning in the Face of Stock Redemption Risks: What You Need to Know

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Estate Planning WYNTK FEATURED

As trusted advisors in the realm of finance and estate planning, we at Tonneson + Co are closely monitoring an upcoming decision by the US Supreme Court that could significantly impact estate planning strategies involving closely held businesses. The case of Connelly v. United States revolves around the complex issue of how life insurance proceeds affect the valuation of redeemed stock in an estate.  

Here’s a breakdown of what’s at stake:  


Brothers Michael and Thomas Connelly, shareholders in the family business Crown C Supply Co., entered into a stock purchase agreement in 2001. This agreement stipulated that upon the death of one brother, the surviving brother would have the option to purchase the deceased’s shares or compel Crown to redeem them using proceeds from a life insurance policy on the deceased brother’s life.  

The Issue

At the heart of the matter is whether the value of the redeemed stock should include the life insurance proceeds. The IRS contends that including the insurance payout in the valuation of the redeemed stock increases the value of the estate, thereby impacting the estate tax liability. On the other hand, the estate argues that the insurance proceeds were offset under the terms of the stock purchase agreement, as they were specifically designated for the redemption of the deceased brother’s shares.  


The outcome of this case could have far-reaching implications for estate planning, particularly for closely held businesses. If the court upholds the IRS’s position, it may introduce greater risks to buy-sell agreements and prompt planners to reconsider recommending this option to clients. Additionally, businesses may face increased financial strain if they are required to include insurance proceeds in their valuation, potentially impacting cash flow and balance sheets.  

What You Need to Consider

As we await the Supreme Court’s decision, it’s essential for business owners and estate planners to stay informed and prepared. Consider the following:  

  1. Review Existing Agreements: If the court rules in favor of the IRS, existing buy-sell agreements may need to be reviewed and possibly revised to mitigate potential tax implications.  
  2. Evaluate Funding Strategies: Explore alternative funding strategies for buy-sell agreements, especially if relying on life insurance proceeds. Assess the impact on cash flow and consider the long-term financial implications. 
  3. Understand Estate Tax Changes: Stay informed about changes to estate and gift tax laws, particularly the temporary expansion set to expire after 2025. This knowledge will help you adapt your estate planning strategies accordingly.  

At Tonneson + Co, we’re committed to helping our clients navigate complex financial matters with clarity and confidence. As developments unfold in the Connelly case, we’ll continue to provide guidance tailored to your unique needs and goals.  

For more information or assistance with your estate planning needs, don’t hesitate to reach out to our team. Your financial peace of mind is our priority.  

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If you’re interested in working with Tonneson + Co, please reach out to us. We look forward to hearing from you!

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