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Supreme Court ruling on life insurance proceeds has estate tax implications

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In a landmark decision earlier this year, the Supreme Court addressed a crucial issue regarding the valuation of shares in closely held corporations for federal estate tax purposes.

The case, Connelly v. United States (2024), clarified whether life insurance proceeds that are used to redeem a deceased shareholder’s stock should be factored into the stock’s valuation for estate tax calculations. The decision has many implications for CPAs, tax professionals, estate planners and investment advisors.

Case overview

Michael and Thomas Connelly were the sole shareholders of Crown C Supply, a closely held building supply corporation. To ensure continuity and to retain ownership within the family, they had a stock redemption agreement funded by corporate-owned life insurance policies worth $3.5 million each. ‘

Upon Michael’s death, the corporation used $3 million from the life insurance proceeds to redeem his shares. But the IRS and the Connelly estate couldn’t agree on the proper valuation of Michael’s shares. The estate valued the shares based on the $3 million redemption payment, but the agency insisted that the life insurance proceeds should be included in the company’s valuation. From the IRS perspective, the proceeds  would raise the total value of the estate to $6.86 million, consequently valuing Michael’s shares at $5.3 million.

This valuation led to a significant additional estate tax liability for the Connelly estate.

Supreme Court decision

The Supreme Court sided with the IRS, affirming that life insurance proceeds should be included in the corporation’s value when determining the value of the decedent’s shares. The court clarified that the obligation to redeem shares at fair market value is not a liability that reduces the corporation’s value for estate tax purposes.

The court’s decision means that the life insurance proceeds used for the redemption would increase the corporation’s total value, thereby increasing the value of the shares held by the deceased at the time of death.

Contradiction in Blount v. Commissioner

The Connelly decision brings to mind the precedent set in Blount v. Commissioner (2005) two decades earlier. In Blount, the Eleventh Circuit concluded that life insurance proceeds should be excluded (not included) from the valuation of a corporation when they are used to fund a stock redemption obligation.

As you can see, the Supreme Court’s recent Connelly decision rejected the Eleventh Circuit’s approach, finding it “demonstrably erroneous.” Again, the Supreme Court emphasized that a redemption obligation does not offset the value of the life insurance proceeds and should be included in the corporation’s value for estate tax purposes.

This divergence highlights the Supreme Court’s intent to provide a clear and unified approach to handling such cases.

Implications for estate planning

This Connelly ruling underscores the importance of strategic planning for closely held businesses to avoid unexpected tax liabilities. Here are three strategies to consider:

1. Cross-purchase agreements. By using a cross-purchase agreement instead of a corporate redemption agreement, the surviving shareholders individually purchase life insurance policies on each other. Upon a shareholder’s death, the surviving shareholders use the proceeds to buy the decedent’s shares directly. This method ensures that the life insurance proceeds do not inflate the corporation’s value for estate tax purposes, since the proceeds are not part of the corporate assets.

Advantages of cross-purchase agreements:

  • Tax efficiency: The insurance proceeds do not increase the corporation’s value, avoiding higher estate taxes.
  • Direct ownership transfer: Shares are directly transferred to surviving shareholders, maintaining business continuity.
  • Flexible ownership structure: This allows for adjustments in ownership percentages without involving the corporation itself.

 Challenges and considerations:

  • Funding requirements: Ensuring adequate funding for the insurance premiums and potential buyouts can be challenging, especially for smaller businesses.
  • Regulatory compliance: The agreement must comply with relevant laws and regulations, which may require professional legal and financial advice.

2. Defensible valuation methods. To prevent disputes and to ensure compliance with tax laws, it is crucial to establish defensible valuation methods within buy-sell agreements. These methods can include binding appraisals conducted by qualified professionals, formula valuations, or regularly updated agreed values.

Best practices for establishing valuation methods:

  • Regular review: Regularly reviewing and updating buy-sell agreements ensures they reflect current business values and comply with evolving laws.
  • Professional appraisals: Using qualified professionals for appraisals can provide a more accurate and defensible valuation.

3. Legal and regulatory compliance. Ensure that buy-sell agreements meet the requirements of Section 2703 of the Internal Revenue Code governing acquisition or transfer of property at less than FMV. This section disregards valuations in buy-sell agreements unless they are bona fide arrangements, not devices to transfer property to family members for less than full and adequate consideration. They must be comparable to similar arrangements in arm’s-length transactions.

The Supreme Court’s decision in Connelly v. United States highlights the need for closely held businesses to reassess their estate planning and buy-sell agreements. By considering alternative strategies like cross-purchase agreements and by ensuring defensible valuation methods, businesses can better manage their estate tax liabilities and ensure smoother ownership transitions. 

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Accounting

XcelLabs launches to help accountants use AI

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Jody Padar, an author and speaker known as “The Radical CPA,” and Katie Tolin, a growth strategist for CPAs, together launched a training and technology platform called XcelLabs.

XcelLabs provides solutions to help accountants use artificial technology fluently and strategically. The Pennsylvania Institute of CPAs and CPA Crossings joined with Padar and Tolin as strategic partners and investors.

“To reinvent the profession, we must start by training the professional who can then transform their firms,” Padar said in a statement. “By equipping people with data and insights that help them see things differently, they can provide better advice to their clients and firm.”

Padar-Jody- new 2019

Jody Padar

The platform includes XcelLabs Academy, a series of educational online courses on the basics of AI, being a better advisor, leadership and practice management; Navi, a proprietary tool that uses AI to help accountants turn unstructured data like emails, phone calls and meetings into insights; and training and consulting services. These offerings are currently in beta testing.

“Accountants know they need to be more advisory, but not everyone can figure out how to do it,” Tolin said in a statement. “Couple that with the fact that AI will be doing a lot of the lower-level work accountants do today, and we need to create that next level advisor now. By showing accountants how to unlock patterns in their actions and turn client conversations into emotionally intelligent advice, we can create the accounting professional of the future.”

Tolin-Katie-CPA Growth Guides

Katie Tolin

“AI is transforming how CPAs work, and XcelLabs is focused on helping the profession evolve with it,” PICPA CEO Jennifer Cryder said in a statement. “At PICPA, we’re proud to support a mission that aligns so closely with ours: empowering firms to use AI not just for efficiency, but to drive growth, value and long-term relevance.”

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Accounting is changing, and the world can’t wait until 2026

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The accountant the world urgently needs has evolved far beyond the traditional role we recognized just a few years ago. 

The transformation of the accounting profession is not merely an anticipated change; it is a pressing reality that is currently shaping business decisions, academic programs and the expected contributions of professionals. Yet, in many areas, accounting education stubbornly clings to outdated, overly technical models that fail to connect with the actual demands of the market. We must confront a critical question: If we continue to train accountants solely to file tax reports, are we truly equipping them for the challenges of today’s world? 

This shift in mindset extends beyond individual countries or educational systems; it is a global movement. The recent announcement of the CIMA/CGMA 2026 syllabus has made it unmistakably clear: merely knowing how to post journal entries is insufficient. Today’s accountants are required to interpret the landscape, anticipate risks and act with strategic awareness. Critical thinking, sustainable finance, technology and human behavior are not just supplementary topics; they are essential components in the education of any professional seeking to remain relevant. 

The CIMA/CGMA proposal for 2026 is not just a curriculum update; it is a powerful manifesto. This new program positions analytical thinking, strategic business partnering and technology application at the core of accounting education. It unequivocally highlights sustainability, aligning with IFRS S1 and S2, and expands the accountant’s responsibilities beyond mere numbers to encompass conscious leadership, environmental impact and corporate governance. 

The current changes in the accounting profession underscore an urgent shift in expectations from both educators and employers. Today, companies of all sizes and industries demand accountants who can do far more than interpret balance sheets. They expect professionals who grasp the deeper context behind the numbers, identify inconsistencies, anticipate potential issues before they escalate into losses, and act decisively as a bridge between data and decision making. 

To meet these expectations, a radical mindset shift is essential. There are firms still operating on autopilot, mindlessly repeating tasks with minimal critical analysis. Likewise, many academic programs continue to treat accounting as purely a technical discipline, disregarding the vital elements of reflection, strategy and behavioral insight. This outdated approach creates a significant mismatch. While the world forges ahead, parts of the accounting profession remain stuck in the past. 

The consequences of this shift are already becoming evident. The demand for compliance, transparency and sustainability now applies not only to large corporations but also to small and mid-sized businesses. Many of these organizations rely on professionals ill-equipped to drive the necessary changes, putting both business performance and the reputation of the profession at risk. 

The positive news is that accountants who are ready to thrive in this new era do not necessarily need additional degrees. What they truly need is a commitment to awareness, a dedication to continuous learning, and the courage to step beyond their comfort zones. The future of accounting is here, and it is firmly rooted in analytical, strategic and human-oriented perspectives. The 2026 curriculum is a clear indication of the changes underway. Those who fail to think critically and holistically will be left behind. 

In contrast, accountants who see the big picture, understand the ripple effects of their decisions, and actively contribute to the financial and ethical health of organizations will undeniably remain indispensable, anywhere in the world.

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Republicans push Musk aside as Trump tax bill barrels forward

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Congressional Republicans are siding with Donald Trump in the messy divorce between the president and Elon Musk, an optimistic sign for eventual passage of a tax cut bill at the root of the two billionaires’ public feud.

Lawmakers are largely taking their cues from Trump and sticking by the $3 trillion bill at the center of the White House’s economic agenda. Musk, the biggest political donor of the 2024 cycle, has threatened to help primary anyone who votes for the legislation, but lawmakers are betting that staying in the president’s good graces is the safer path to political survival.

“The tax bill is not in jeopardy. We are going to deliver on that,” House Speaker Mike Johnson told reporters on Friday.

“I’ll tell you what — do not doubt, don’t second guess and do not challenge the President of the United States Donald Trump,” he added. “He is the leader of the party. He’s the most consequential political figure of our time.”

A fight between Trump and Musk exploded into public view this week. The sparring started with the tech titan calling the president’s tax bill a “disgusting abomination,” but quickly escalated to more personal attacks and Trump threatening to cancel all federal contracts and subsidies to Musk’s companies, such as Tesla Inc. and SpaceX which have benefitted from government ties.

Republicans on Capitol Hill, who had —  until recently — publicly embraced Musk, said they weren’t swayed by the billionaire’s criticism that the bill cost too much. Lawmakers have refuted official estimates of the package, saying that the tax cuts for households, small businesses and politically important groups — including hospitality and hourly workers — will generate enough economic growth to offset the price tag.

“I don’t tell my friend Elon, I don’t argue with him about how to build rockets, and I wish he wouldn’t argue with me about how to craft legislation and pass it,” Johnson told CNBC earlier Friday.

House Budget Committee Chair Jodey Arrington told reporters that House lawmakers are focused on working with the Senate as it revises the bill to make sure the legislation has the political support in both chambers to make it to Trump’s desk for his signature. 

“We move past the drama and we get the substance of what is needed to make the modest improvements that can be made,” he said.

House fiscal hawks said that they hadn’t changed their prior positions on the legislation based on Musk’s statements. They also said they agree with GOP leaders that there will be other chances to make further spending cuts outside the tax bill. 

Representative Tom McClintock, a fiscal conservative, said “the bill will pass because it has to pass,” adding that both Musk and Trump needed to calm down. “They both need to take a nap,” he said.

Even some of the House bill’s most vociferous critics appeared resigned to its passage. Kentucky Representative Thomas Massie, who voted against the House version, predicted that despite Musk’s objections, the Senate will make only small changes.

“The speaker is right about one thing. This barely passed the House. If they muck with it too much in the Senate, it may not pass the House again,” he said.

Trump is pressuring lawmakers to move at breakneck speed to pass the tax-cut bill, demanding they vote on the bill before the July 4 holiday. The president has been quick to blast critics of the bill — including calling Senator Rand Paul “crazy” for objecting to the inclusion of a debt ceiling increase in the package.

As the legislation worked its way through the House last month, Trump took to social media to criticize holdouts and invited undecided members to the White House to compel them to support the package. It passed by one vote.

Senate Majority Leader John Thune — who is planning to unveil his chamber’s version of the bill as soon as next week — said his timeline is unmoved by Musk. 

“We are already pretty far down the trail,” he said.

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