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The Returns

Last Friday, December 30, 2022, during the final hours of the 117th Session of Congress, the House Ways and Means Committee – through which all tax legislation passes[i] – released redacted versions of six years of Mr. Trump’s annual federal income returns.

I told myself months ago that I would not waste my time reviewing the returns if they were ever made public. However, after several acquaintances peppered me with questions regarding the returns over the long holiday weekend, I relented and quickly skimmed the earliest of the returns, for 2015.

Continue Reading Trump’s Returns and Congress – Lessons, Next Steps?
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Lately I’ve been thinking about the many ways by which members of the public transfer funds to government and the many reasons for which such transfers are made. After all, we’re still in the “season of giving.”[i]

Continue Reading New York’s “No-Longer-a-Sin” Taxes – Effective? Progressive? Neither?
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Taxing the Rich

During the last couple of months, as we headed into what most folks – excluding transactional attorneys – call the “Holiday Season,”[i] tax authorities from around the globe have been calling for increased taxes on the rich, however one chooses to define this class of individuals.

The chief economist for the European Central Bank, relying on macroeconomic policy and concepts of “fairness,” advised governments to tax the rich to support society’s vulnerable groups.[ii]

In the U.K., His Majesty’s Revenue & Customs announced an initiative to pursue tax fraud by the wealthy and mid-size businesses. In fact, it has been reported that HMRC plans to go so far as to assign agents to personally monitor the tax affairs of certain individuals – an odd variation on the “buddy system.” Continue Reading Pigs Get Fed, and Pay Their Taxes, But Hogs – That Remains to be Seen

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Don’t Be Unreasonable

Much has been written of late regarding the payment by a business of various personal expenses incurred by its owner or certain key employees.

The payment of an owner’s personal expenses appears to violate a basic precept of the tax law with respect to the use of business assets[i] – specifically, that their use be limited to furthering the purposes and interests of the business.

This precept emanates from what is perhaps the golden rule for dealings between a closely held business and any of its owners and “related” persons: that they transact with one another on terms that are as close to arm’s length as practicable. Continue Reading Transacting With One’s Business – Keep It Arm’s Length

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Denial

It wouldn’t be far-fetched to say that, as a species, we humans have a propensity – rooted in our instinctive tendency for self-preservation – toward denying anything we believe may cause us harm. It should come as no surprise that this natural inclination has found expression in the arts. For example, there are certain lyrics and movie scripts that include lines that are memorable only because they recall this defense mechanism called “denial.”

For example, the artist known as Shaggy[i] created a song around two[ii] simple words with which countless children and former children have responded to a variety of accusatory questions: “Wasn’t me.” Continue Reading Personal Liability for NY Sales Taxes –Sometimes, There’s No Denying It

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Related Party Transactions – In General

To avoid the manipulation of tax consequences to which transactions between certain related[i] taxpayers may be susceptible, the IRS and the Courts generally require that such transactions be closely scrutinized to ensure that the form of the transaction reflects its underlying economic reality,[ii] and that the tax consequences arising therefrom are consistent with those arising from transactions between unrelated parties dealing at arm’s length with one another.[iii]

Similarly, the Code and the regulations promulgated thereunder have long recognized that a taxpayer who engages in certain transactions with another party should be denied a particular tax benefit that would otherwise be realized from the transaction if the taxpayer and the other party bear a certain relationship to one another and if the sought-after tax benefit is inconsistent with the economic consequences of the transaction. Continue Reading Related Party Transactions Converting Gain Into Ordinary Income – Be Careful Out There

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I am guessing that, later this week, many if not most of us will celebrate our uniquely American holiday, Thanksgiving Day. Hopefully, we will be fortunate enough to spend the day and share a meal with family and friends. With a bit of luck, politics will not find its way into our conversations and work will not intrude upon our time at home.

I’m willing to bet that turkey[i] will be on the menu – whether roasted or fried, whole, quartered, or segmented in some other way[ii] – alongside lasagna, moussaka, tandoori chicken, sauerbraten, rice and beans, perogy, goulash, couscous, kebab, borscht, empanada, chicken teriyaki, falafel, lamb, or whatever else our people brought with them when they came to this country.

As wonderful as the Thanksgiving holiday is, for historical reasons I have always associated it with federal taxes. Wait a minute, just hear me out.

Continue Reading Thanksgiving and. . . Taxes?

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The Mid-Terms

With 50 seats in the Senate, the Dems still control that Chamber. A win in the Georgia runoff, however, may lessen the burden for Majority Leader Schumer by, perhaps, neutralizing the significance of a certain member of his own party.[i]

Meanwhile, the GOP has claimed “control” of the House by a very thin margin,[ii] but the party’s leadership is already being challenged by its more conservative members.[iii]

On the other side of the aisle, moderate Dems in the House are certainly taking notice of how well the elections went for the “progressive” wing of their party.[iv]

Politics being what it is, would it surprise you if nothing happened in Congress for the next two years? Probably not. Continue Reading Thinking About Leaving New York? Don’t Forget to Check Your Federal Tax Return

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Priority Guidance Plan

Some folks eagerly await the release of a new album. Others camp outside of big box retailers to get the jump on holiday gifts. There are those who line up at box offices to purchase tickets for a concert that is months away. Then there are some who might as well be sitting on pins and needles after they’ve learned that their favorite tech company is about to announce the arrival of their latest “must-have”[i] gadget. Continue Reading Sale to IDGT, Death of Grantor, Basis Step-Up: Treasury’s Priority Guidance & the Dems’ Loss of the House

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The Key Person

The closely held corporation is often a fragile creature. Too often, its continued success and well-being are overly dependent upon the continued involvement of one individual – namely, the founder and principal owner of the corporation’s business.

This strong-willed individual may be responsible for the day-to-day management and operation of the business. Their relationships with the customers and vendors of the business, and with the business community generally, may represent a significant part of the corporation’s goodwill. Continue Reading Trusts, the Death of a Shareholder, and The S Corporation Election