The Connelly Case Is a Wake-Up Call for Business Owners

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Business owners who once felt confident in the security of their buy/sell agreements may need to reconsider their strategies following a landmark Supreme Court ruling this summer. The decision in the “Connelly case” upheld the IRS’ position on how life insurance proceeds should be treated for federal estate tax purposes, sending ripples through the business community.

The case serves as a stark reminder that even well-established agreements may not be sufficient. For business owners, this underscores the importance of revisiting — or potentially rethinking — their succession plans to avoid unintended financial and/or legal consequences.

The Connelly case originated after an owner of Crown C Supply, a family-owned business, passed away. When the deceased owner’s brother declined to purchase his shares, the company was obligated to redeem them using life insurance proceeds. This action inadvertently increased the valuation of the firm, leading to a higher estate tax liability.

The case highlights a critical flaw in many buy/sell agreements — they often fail to account for the complexities of business growth and changing tax regulations. Buy/sell agreements — which are legally binding contracts outlining how shares are managed in the event of an owner’s death, disability, retirement, or departure — are a cornerstone of business succession planning. However, as the Connelly case demonstrates, these agreements can become outdated or inadequate, leaving businesses vulnerable to significant financial risks.

The ruling is a wake-up call for business owners to reassess their succession plans for potential adjustments. With the Supreme Court’s decision shifting the tax and legislative foundation, the legacy and future of many businesses may be at risk. To safeguard their interests, business owners should consult with wealth managers who offer comprehensive services tailored to their unique situations. By doing so, they can avoid the pitfalls that befell Crown C Supply and ensure their businesses remain protected.