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Challenge to Collection Due Process? Will Supreme Court Affirm IRS’s Offset of Valid Refund With Disputed Tax Liability?

Earlier this year the IRS announced that, as part of its larger compliance efforts begun last fall under the Inflation Reduction Act, the agency’s stepped-up enforcement activity with respect to high wealth, high income...more

Thinking About Making Taxable Gifts Before the 2026 Sunset?

As we will see shortly, it is often “better to give than to receive,” though this statement begs the obvious question of whether it is better to do so during one’s lifetime or upon one’s death. Many well-to-do individuals...more

New York Tax Continues to Inconvenience Nonresidents Working Remotely

Last Friday, New York’s Governor Hochul delivered the following remarks at the annual meeting of the Business Council of New York State:“Someone asked me today, are we going to raise income taxes? I said, ‘I’m not raising...more

Unconstitutionally Excessive FBAR Penalties? It Depends

You may recall that earlier this year the IRS launched an initiative to pursue 125,000 “high-income, high-wealth” taxpayers who have not filed taxes since 2017. These were cases where the IRS received third party information...more

New York’s Tax Treatment of Compensatory Restricted Stock and Dividends in the Hands of a Nonresident Executive

As far back as I can remember, the end of August has always elicited a sense of dread comparable to what many schoolchildren, and a fair number of adults, experience every Sunday afternoon. In retrospect, I cannot say that...more

When A Shareholder Loses Control of Their S Corporation

If given their druthers, most transactional corporate attorneys would prefer to spend their day practicing “happy law,” by which they typically mean transactions that involve capital formation, mergers and acquisitions, joint...more

Taxing A Foreigner’s Sale of a Partnership Interest – Déjà Vu All Over Again

There is no denying that many parts of the Code are complex and, in some cases, too obscure for many “laypersons” to comprehend. Over time, this reality spawned the need for advisers who are both knowledgeable and experienced...more

Swapping Foreign Real Properties On a Tax Deferred Basis

Over the last couple of years, several of my friends have become citizens of the country from which their parents emigrated to the U.S. Also during that period, some acquaintances took advantage of the so-called “golden...more

Tax Considerations and the Reclassification of Marijuana – We’re Not There Yet

Having been swept along for nine days “by the force of the hostile winds on the fishy sea,” Odysseus and his crew came to a strange land. After securing their ships, Odysseus sent some of his “companions ahead, telling them...more

The Supreme Court’s Non-Opinion On The “Realization” of Income – A Lost Opportunity?

In less than four months, the citizens of the United States will be electing their next President to a four-year term. They will also be deciding which of the two major political parties will “control” the Senate, the House,...more

Funding the Buyout of a Deceased Shareholder With Corporate-Owned Life Insurance – Did the Court Decide Connelly Correctly?

You may have heard or even read about the U.S. Supreme Court’s recent decision regarding the date of death value of a deceased shareholder’s shares in a closely held corporation that owned a life insurance policy on the...more

Trust Beneficiary Engages In Like Kind Exchange Using Trust Property

It is a basic principle of the income tax that the gain or loss realized by a taxpayer from the conversion of property into cash, or from the exchange of property for other property that differs materially in kind from the...more

Collecting an Individual’s Unpaid Taxes from Their Controlled Entities

An anonymous thinker, lost to history, is credited with having said that the unofficial motto of the IRS is, “We have what it takes to take what you have.” In some instances, the truth of the above statement is manifested in...more

Tax Authorities of the World Unite? Not Quite, But the IRS Joins the Movement to Tax the Rich

Earlier this year, the OECD observed there has been a significant increase in global wealth inequality over the last two decades. It also acknowledged that “taxation is a key instrument . . . that governments have at their...more

Partnership Transactions Lacking Economic Substance or Business Purpose: Investor Beware

Assume that X and Y agree to the following: X will transfer ownership of Prop to Y, and Y will transfer cash to X. What just happened? Obviously, X has sold Prop to Y. If the amount of cash that X receives is greater than...more

Missing the Tax Court’s 90-Day Deficiency Deadline – Now What?

Over the years, I have observed there is only one thing that a taxpayer fears more than being notified by the IRS that their income tax return for a particular taxable year has been selected for audit, and that is being...more

IRS Cannot Offset Taxpayer’s Refund With A Disputed Tax Liability

Imagine the IRS notifies Taxpayer that they have an outstanding tax liability with respect to Tax Year, and that the agency intends to levy on Taxpayer’s property to collect the allegedly unpaid tax. Taxpayer challenges the...more

An Inveterate Golfer At the IRS

As we approach the deadline for paying federal individual income taxes and, generally, for filing the returns on which such taxes are determined, some of you may be recalling how the Inflation Reduction Act of 2022...more

Trust Fund Recovery Penalty & The Closely Held Business

Depending upon what you read or, perhaps more accurately, depending upon how much you believe of what you read, you may be aware that many closely held businesses are concerned about their future. Most of these survived...more

“C’mon Man! Tax the Rich!” Business Owners Face Tax Increases*

Last week, Sen. Warren reintroduced her “Ultra-Millionaires” wealth tax proposal to the Senate. Query her timing. The measure has the proverbial snowball’s chance in Hell of being enacted by this Congress.Perhaps the Senator...more

Estate, Gift, GST & Related Income Tax Proposals – What is the White House Doing?

Earlier this week the White House released its Fiscal Year 2025 Budget. Of course, the federal government has not yet adopted a budget for the Fiscal Year 2024 even as we approach that year’s halfway mark. But I digress. The...more

Rescission, Repossession, Real Estate – The Three R’s of Unwinding a Sale

How many times have you wished that you could undo something from your past, perhaps a string of incoherent statements made at a client dinner while slightly under the influence, or an expletive-filled email composed and sent...more

Transfers Within the Family Business: Gifts or “Ordinary Course” Transactions?

It is not uncommon, in the context of a business entity in which a family owns a controlling or substantial interest, for an adviser to encounter intersecting gift and income tax issues. This week’s post will consider one...more

Shareholder-Transferee Liability for a Corporation’s Income Tax

Would you be surprised to learn that most shareholders of closely held corporations, and especially those with minority or merely passive interests, believe they cannot be held responsible for the tax obligations of their...more

The Family-Owned Business, Stock Options, And Personal Goodwill – a Smorgasbord of Tax Issues

Many of us have encountered variations of the following scenario: a parent owns and operates a business; one or more of their children are employed in the business; as the children mature and become more experienced and...more

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