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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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Scammers are ‘relentless’ this tax season: IRS

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Talk of probationary workers, layoffs and cutbacks may be new, but one annual constant continues this season: tax scams.

The Internal Revenue Service says that from email schemes to misleading tax credits, many of the most popular frauds are robust during the year but peak during filing season.

“Scammers are relentless, and they use the guise of tax season to try tricking taxpayers into falling into a variety of traps. These red flags can lead to everything from identity theft to being misled into claiming tax credits for which they’re not entitled,” said IRS communications senior adviser Terry Lemons in a statement.

Let’s look at the latest in relentless from the IRS’s annual Dirty Dozen.

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Private sector slowed hiring in February, says ADP

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Private sector employers added 77,000 jobs in February, while annual pay grew 4.7% year over year, payroll processor ADP reported Wednesday.

Hiring slowed to the smallest level since July, with trade and transportation, health care and education, and information showing job losses. Small business employment also declined. The service-providing sector added 36,000 jobs in February, including 27,000 in professional and business services such as accounting and tax preparation. The goods-producing sector added 42,000 jobs, including 26,000 in construction and 18,000 in manufacturing, offset by losses of 2,000 jobs in the natural resources and mining sector.

“This is the first time in seven years that we saw goods-producing firms outpace service-providing firms in hiring,” said ADP chief economist Nela Richardson.

Small businesses lost 12,000 jobs, including 17,000 in businesses with between one and 19 employees, partially offset by a gain of 5,000 jobs in businesses with between 20 and 49 employees. Medium-size establishments gained 46,000 jobs, including 15,000 at businesses with between 50 and 249 employees, and 31,000 at businesses with between 250 and 499 employees. Large businesses with 500 or more employees added 37,000 jobs for the month.

For people who changed jobs, the year-over-year pay gains slowed slightly, from 6.8% in January to 6.7%. Pay gains for those who stayed at their jobs were flat at 4.7%. For professional and business services, the rate for job stayers was 4.5%.

“With 4% unemployment, we’re still seeing pretty robust supply and demand in the labor market, and it’s still a market where there’s a balance, and that requires small firms to keep pace in terms of wage growth,” said Richardson. “They may, in some sense, be losing traction in terms of pay growth to those larger firms. That might be one of the reasons we see some weakness there.”

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Trump hails tariffs as economy barrels into trade wars

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President Donald Trump took the lectern Tuesday for his primetime address beset by warning signs about the U.S. economy, and acknowledged to Americans there could be more discomfort ahead.

Trump defended his plan to remake the world’s largest economy through the biggest tariff increases in a century, saying it would raise “trillions and trillions” in revenue and rebalance trading relationships he called unfair. He cast the economic pain the levies are expected to cause in the form of higher prices as a “little disturbance” the nation ought to be able to overcome.

“Tariffs are about making America rich again and making America great again. And it’s happening, and it will happen rather quickly,” he said. “There’ll be a little disturbance, but we’re OK with that. It won’t be much.”

For large swaths of his record-setting 100-minute joint address to Congress on Tuesday night, though, Trump preferred to spend time on issues he sees as his political strengths. He hammered topics like transgender rights, migrant crime and diversity, equity and inclusion, and said relatively little about consumer prices.

The president proclaimed he was leading a “common-sense revolution,” saying “our country will be woke no longer.”not supported.

Trump turned to inflation only after a 19-minute opener. He blamed high prices for eggs and other goods on his predecessor, Joe Biden, and offered few new ideas to lower costs.

Some of his proposals at times sounded like magical solutions, including complex energy projects that could take years to complete and using savings from Elon Musk’s cost-cutting campaign, which have amounted to a small fraction of the federal deficit, to help pay down the debt.

The speech came at a pivotal moment. The president’s approval rating, which was positive in the weeks after his November election victory, has gone underwater in a series of polls. Data shows new strains on the economy as factory activity stagnates, inflation simmers, consumer confidence ebbs, and stocks lag behind equity markets in other countries. 

Hours before he spoke, the S&P 500 Index closed at its lowest level since before the November election as Trump’s threats of trade wars with Canada and Mexico became a reality.

U.S. stock futures pointed to a turnaround on Wednesday, partly tied to Commerce Secretary Howard Lutnick saying the administration was already considering limited relief for the North American neighbors hit Tuesday with 25% tariffs on most of their shipments to the US.

An effort to disrupt Trump’s address by Democratic Representative Al Green was drowned out by Republican jeers and the lawmaker was escorted out of the chamber. Other Democrats held up signs with slogans such as “Musk Steals” and “False,” that were mocked on social media. 

“I could find a cure to the most devastating disease,” Trump replied. “And these people sitting right here will not clap.”

In the face of challenging events, he has often resorted to his showmanship and ability to command the nation’s attention to avoid political damage. 

Trump highlighted the heart-wrenching stories of invited guests, including freed American hostages. A 13-year-old boy diagnosed with cancer with ambitions of becoming a police officer was made a Secret Service agent by the agency’s director and Trump told a high school senior that he had earned admission to the US Military Academy at West Point.

Border security

He touted his immigration and border policies, which have ramped up deportations of undocumented migrants and designated Mexican cartels and other foreign gangs as terrorist organizations. He called on Congress to pass additional funds for border security. 

But similar to the economy, the campaign promises that Trump made during the 2024 election have collided head-on with the realities that he’s confronted back in the White House. Inflation is tough to tame and wars are difficult to resolve.

On the world stage, the president sought to cast himself as a peacemaker, even as he boasted about withdrawing the U.S. from international institutions. He praised Ukrainian President Volodymyr Zelenskiy for saying he would accept a natural resources deal that was scuttled last week after a disastrous meeting at the White House, while reiterating his demand for an end to the conflict and expressing reservations about continued U.S. military aid to Kyiv.

Trump spoke just hours after hitting Canada and Mexico — the nation’s largest trading partners — with the new tariffs and doubling levies on Chinese imports to 20%. While those moves are aimed at boosting domestic jobs and production in his vision for a “golden age of America,” economists warn that trade wars will reignite inflation, close export markets for US businesses and weigh on consumer sentiment.

Trump reiterated his threat to impose 25% tariffs on aluminum and steel and to put in place reciprocal tariffs on all countries with barriers to American imports, saying that the U.S. had been “ripped off for decades by nearly every country on Earth, and we will not let that happen any longer.”

“Whatever they tariff us, we tariff them,” Trump said. “Whatever they tax us, we tax them. If they do non-monetary tariffs to keep us out of their market, then we do non-monetary barriers to keep them out of our market.”

Trump touted his tariff moves as more effective at bringing jobs to the U.S. than Biden’s efforts, which included the Chips and Science Act and its billions in subsidies to spur domestic semiconductor manufacturing. Trump urged lawmakers to eliminate the Chips Act and said he would not give chipmakers any more funds from the law.

Separately, Trump announced plans to establish an office of shipbuilding at the White House. And he said he had spoken to the heads of the three largest U.S. automakers Tuesday before his speech. Car companies are particularly concerned that the tariffs on Mexican and Canadian goods could ratchet up prices even on vehicles assembled in the U.S.

Trump is casting his bid to spur domestic energy production as an antidote for inflation. Yet he has yet to implement potential policies that could encourage more domestic oil demand or lower the costs of energy production. And even so, it’s not clear the oil industry will go along. Oil executives who suffered huge losses from collapsing energy prices during the coronavirus pandemic have shown little appetite to dramatically bolster output as they focus on shareholder returns.

Even Trump’s bid to invigorate a long-stalled natural gas pipeline and export project in Alaska would take years to construct, delivering only limited dividends for American consumers, while supplying the fuel to residents inside the state and Asian allies abroad.

In his second term, Trump has moved rapidly to implement his policies with a stream of executive actions that are reshaping the U.S. government and its economic and security ties with the world.

Musk’s DOGE cuts

Musk, who is overseeing an effort to slash the federal government’s workforce and spending through the Department of Government Efficiency, was in the chamber and received a standing ovation from Republicans. 

Those moves have led to consternation throughout Washington and concerns even from some Republicans over their scope. Democrats highlighted that wariness, with some lawmakers inviting former government workers who lost their jobs..

Trump gave a lengthy list of government programs and grants he cast as examples of waste, and reiterated previous claims — since walked back by other government officials — suggesting that Social Security was providing benefits to people hundreds of years old. Democrats frequently interjected to jeer the claims.

Trump’s appearance before Congress presented a crucial opportunity to press fellow Republicans on legislative action. The party is grappling with how to extend expiring tax cuts from Trump’s first term, approve additional benefits he promised during the campaign, and his calls to balance the budget. 

“I’m calling for no tax on tips, no tax on overtime and no tax on Social Security benefits for our great seniors,” Trump said.

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