IRS Determines Corporation Provided Brokerage Services; Taxpayer Denied QSBS Gain Exclusion

Compliance, Income Tax, Tax, Tax Controversy, TCJA

In a recent Chief Counsel Advice (“CCA”) issued by the IRS, the IRS concluded that the taxpayer’s sale of stock did not qualify for the gain exclusion as Qualified Small Business Stock (“QSBS”) under Section 1202 since the business of the corporation was akin to brokerage services.[1] The IRS concluded that the corporation’s business, one…
Read More

Court Says No to IRS Attempt to Aggregate Gifts for Discount Purposes

Cases, District Court, Estate and Gift Tax, Estate Planning, Tax, Tax Controversy

In a recent case out of the United States District Court for the District of Connecticut, the Court denied the IRS’ motion for summary judgment and refused to aggregate the gift of partial interests in real estate together for purposes of valuing the gifts and thus determining appropriate discounts.[1] The IRS alleged that no discount…
Read More

Injunctive Relief Hiding in Plain Sight? CIC Services, LLC v. IRS

Cases, District Court, Income Tax, Tax Controversy

So, we did not write on the first District Court case which was a loss for CIC Services, LLC (“CIC”) and Ryan, LLC(“Ryan”), the Plaintiffs. But, a Supreme Court decision gave the Plaintiffs another bite at the apple. This case involves Notice 2016-66 (“Notice”), the older-sibling notice to Notice 2017-10, in which micro-captive insurance transactions…
Read More

IRS Demands iTunes Cards? Beware the Dirty Dozen!

Charitable Giving, Compliance, Current Events, Income Tax, Tax, Tax Controversy

In January of 2002 the Internal Revenue Service (“IRS”) issued a press release highlighting a dozen different tax scams and encouraged taxpayers to “maintain national vigilance.”[1] This list was dubbed the “Dirty Dozen,” and the IRS has continued to issue similar press releases containing updated lists of purported tax scams for taxpayers to be on…
Read More

Executor Liability for Decedent’s Tax Obligations

Cases, Estate Administration, Estate and Gift Tax, Fiduciaries, Tax, Tax Controversy, Tax Court

A recent Tax Court opinion[1] highlights one of the risks of serving as executor or administrator of an estate, potential liability for a decedent’s tax obligations. The case involves application of the federal priority statute[2] applicable to fiduciaries.[3] That statute provides, in relevant part, that “a representative of a person or an estate (except a…
Read More

Corporation Liable for Employment Tax on Reasonable Compensation of Corporate Officers

Employment Tax, Income Tax, Tax Controversy, Tax Court

In a recent Tax Court case, the Court determined that corporate officers were indeed employees of the corporation entitled to reasonable compensation, and as such, the corporation is liable for employment taxes on reasonable compensation imputed to the corporate officers.[1] Mr. and Mrs. Hacker, who owned 51% and 49% of Blossom Day Care Centers (“Blossom”)…
Read More

Substance over Form: Friend of the Taxpayer?

Cases, Current Events, Income Tax, Tax Controversy, Tax Court

In the recent Complex Media[1] case, the Tax Court addressed a taxpayer’s ability to recast the form of a transaction under the “substance over form” doctrine. Since taxpayers typically control the form their transactions take, tax decisions routinely stick taxpayers with the consequences of that form. Some courts have precluded taxpayers from even raising substance…
Read More

Directions