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Posts from September 2014.

S corporations and their shareholders must keep track of stock and debt basis.  Failure to do so can lead to disastrous results.  Nathel v. Commissioner, 105 AFTR 2d 2010-2699 (2d Cir 2010), illustrates this point.

In Nathel, the government and the taxpayer stipulated to the facts.  Two brothers and a friend formed three separate S corporations to operate food distribution businesses in New York, Florida and California.  All three shareholders made initial capital contributions to the corporations.  The brothers also made loans to two of the corporations.

In 2001, one corporation was liquidated.  In a reorganization of sorts, the friend ended up owning 100% of the second corporation and the two brothers ended up equally owning the third corporation.

In late 2000, before the reorganization, the brothers made loans to the corporations totaling around $1.3 million.  In 2001, they made capital contributions totaling approximately $1.4 million.  Also, in 2001, they received loan repayments combined in excess of $1.6 million.

Immediately before the repayment of the loans, the brothers had zero basis in their stock and only nominal basis in the loans.  Ouch!  To avoid the ordinary income tax hit on the delta between the $1.6 million in loan repayments and their nominal loan basis, the brothers, with the likely help of their handy dandy tax advisor, asserted the $1.4 million in capital contributions was really tax-exempt income to the corporation, excludable under IRC Section 118(a), but which, under IRC Section 1367(b)(2)(B), increased their loan basis.  Therefore, the ordinary income tax hit on the loan repayments was nominal.

The Nathel brothers were correct about one point - - under IRC Sections 1366 and 1367, if the corporation had income, including tax-exempt income, such would restore debt basis to the extent of their share of that income.  The Service pointed out to the Nathel brothers, however, that they were wrong about the most important point:  capital contributions, in accordance with IRC Section 118, are not income to the recipient corporation.  So, since the corporation had no income, there was no loan basis restoration.  The additional capital contributions did, however, increase their stock basis, which may be of help to the Nathel brothers down the road.  Additional stock basis, however, was of no help to the Nathel brothers as it did not reduce the tax burden resulting from the loan repayment.

  • The taxpayers lose the debate;
  • The IRS issues a 90-day letter; and
  • The Nathel brothers are off to Tax Court.

The Nathel brothers, of course, lose again!  Rather than stay down for the count, they proceed forward to the Second Circuit Court of Appeals, where they lose a third time.

There are two morals to this story:

  1. Capital contributions are not income to the recipient corporation for purposes of IRC Sections 1366 and 1367; and
  2. Shareholders of S corporations need to keep track of stock and debt basis to avoid the unpleasant tax news the Nathel brothers received in this case.

In a recent GAO report that looked at tax years 2006 through 2008, the government found that losses deducted by S corporation shareholders that exceeded basis limitations totaled around $10,000,000, or amounted to about $21,600 per shareholder/taxpayer. The GAO concluded that this non-compliance is the consequence of the actions of the shareholder, not the corporation.  In other words, it is the shareholders’, not the corporation’s, duty to track and compute stock basis.  Don’t be surprised, however, if Congress does not amend the law, requiring S corporations to compute each shareholder’s basis and include it on the IRS Form K-1 each year.  Partnerships already have this duty in that they have to report the partner’s beginning and ending capital account balances on the IRS Form K?1 each year.

S corporations and their shareholders must track both stock and debt basis.  It is that simple.

Please join me for the NYU 73RD Institute on Federal Taxation.  This year’s Institute will be held in San Diego at the Hotel Del Coronado November 16 – 21, and in New York City at the Grand Hyatt New York October 19 – 24.  Please see the attached brochure.  The coverage of tax topics is both timely and broad.  This year’s presentations will cover topics in the areas of:  executive compensation and employee benefits; partnerships and LLCs; corporate tax; closely held businesses; and trusts and estates.  What is so terrific about the Institute, in addition to a wonderful faculty and the interesting current presentation topics, you can choose the presentations you want to attend.  In other words, you can pick and choose the topics that relate to your tax practice.

This is my second time speaking at the Institute.  My topic this year is: "Developments In The World Of S Corporations."  I plan to deliver a White Paper that will provide attendees with an historic overview of Subchapter S and a look through a crystal ball at the future of Subchapter S, including a review of the recent cases, rulings and legislative proposals impacting Subchapter S.

I hope to see you in either San Diego or New York.



The IRS will strike down transactions among related parties that lack economic outlay. At least two recent US Tax Court cases are illustrative of the issue.


Kerzner v. Commissioner, T.C. Memo 2009-76 (April 6, 2009). The Service beat the taxpayers in this case by a nose. Mr. and Mrs. Kerzner were equal partners in a partnership that owned a building. The partnership leased the building to an S corporation which was owned equally by two shareholders, Mr. and Mrs. Kerzner. Over the years, the partnership loaned the Kerzners money. In turn, they loaned the money to their S corporation, which used the money to pay rent to the partnership.

At the end of each year, promissory notes were drafted to document the loans; some of the notes stated an interest rate, some did not. Even though the notes required payment of principal, virtually no payments were ever made because the notes each year were replaced with new notes before any payment was due.

The S corporation had large losses. The Kerzners claimed basis in the loans to the corporation and took the losses on their individual tax returns. Upon audit, the Service claimed the loans lacked economic substance and did not give the Kerzners basis to absorb the losses.

Two points of law need to be understood:

  • First, in accordance with Code Section 1366(d)(1), the losses taken by the Kerzners cannot exceed their adjusted basis in the stock, plus their adjusted basis in any loans from them to the corporation; and
  • Second, basis is only obtained in loans if: (i) the corporation owes the debt directly to the shareholders; and (ii) the shareholders really made an economic outlay that rendered them poorer. There must be economic substance—the loans must be real.

In this case, the money started with the partnership and ended with the partnership. Because it is likely no cash ever actually exchanged hands and only a mere after-the-fact paper trail was created, there was no economic substance. Consequently, the US Tax Court disallowed the losses.

The Kerzners could have changed the result!

  • They could have taken a real distribution from the partnership and loaned it to the S corporation, and required the corporation to make monthly payments of principal and interest;
  • They could have borrowed money from a bank and loaned it to the S corporation, and required it to make monthly payments of principal and interest; or
  • They could have used their own resources and loaned money to the S corporation and required it to make monthly payments.


The 2012 tax court memo case of Maguire v. Commissioner sounds a lot like the saga of the Kerzners.

Like the Kerzner case, this is also a Tax Court Memorandum case. A Memorandum Opinion is generally only issued in a case that does not involve a novel legal issue. Like Kerzner, this case definitely did not involve a novel legal issue. Its outcome, however, is debatable.

While the facts and legal issues in this case are much like the Kerzner case, the outcomes are opposite.

Maguire v. Commissioner, T.C.M. 2012-160 (June 6, 2012). The Maguires, husband and wife, owned two S corporations. The businesses of the corporations were related. One corporation operated an automobile dealership. The other corporation operated a finance company that purchased customer notes from the dealership. The finance company operated at a profit while the automobile dealership operated at a loss. The Maguires did not have sufficient basis in the dealership to deduct the losses. They had substantial basis, however, in the finance company.

The Maguires could have fixed the problem. In a reorganization, they could have formed a parent holding company, an S corporation, and put the two corporations downstream as wholly-owned subsidiaries, and made QSub elections. This would have totally resolved the problem. Unfortunately, they had a minority owner in each entity that would not agree to the reorganization.

The Maguires came up with what they thought was the next best solution. At the end of each year, the finance company owned substantial A/R from the dealership. So, the Maguires caused the finance company to distribute the A/R to them; they had substantial basis to absorb the distribution without tax. Then, they contributed the A/R to the dealership, freeing up the losses with their newly found basis. The transactions were allegedly contemporaneously documented in minutes and the books of both corporations. The underlying customer notes were real and legally binding.

The Service disallowed the losses, arguing the actions between the related entities and the Maguires lacked any economic outlay. This was the same argument the government asserted in Kerzner. Although the transactions were documented by journal entries and corporate resolutions, the parties’ economic positions were not altered.

Losses deductible by a shareholder are limited to his or her basis in the corporation under Code Section §1366(d). A shareholder’s basis in the corporation is increased by capital contributions. To qualify as a capital contribution, the shareholder must make an actual economic outlay.  The US Tax Court disagreed with the IRS. Judge Ruwe found the “distributions and contributions did have real consequences that altered the positions of petitioners individually and those of their businesses.” There was an economic outlay.

The court’s decision hinged on several key facts, including:

  • The transactions were properly memorialized in minutes of both corporations;
  • The transactions were properly recorded in the books of both corporations;
  • The underlying customer notes were real; and
  • The accounts receivable were legally enforceable, and thus had value.


The facts in Maguire are strikingly similar to the facts presented to the court in Kerzner.  The only real difference is that, in Maguire, there was credible evidence that the documentation was done contemporaneously with the transactions each year. Whether economic outlay exists is a question of fact. A few takeaways from Maguire and Kerzner relative to transactions among related parties include:

  • Documentation is king. Transactions must be properly documented in the records of the related entities;
  • The documentation should be contemporaneous with the transactions; after the fact documentation should be avoided;
  • An actual transfer of funds should occur;
  • The agreements need to have real consideration and be legally binding; and
  • Caution is always required when transactions occur among related parties.

Kerzner and Maguire should serve as lessons for tax advisors. Transactions among related entities will be closely scrutinized. Economic substance must exist to withstand the attack.


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Larry J. Brant

Larry J. Brant is a Shareholder in Foster Garvey, a law firm based out of the Pacific Northwest, with offices in Seattle, Washington; Portland, Oregon; Washington, D.C.; New York, New York, Spokane, Washington; and Beijing, China. Mr. Brant practices in the Portland office. His practice focuses on tax, tax controversy and transactions. Mr. Brant is a past Chair of the Oregon State Bar Taxation Section. He was the long-term Chair of the Oregon Tax Institute, and is currently a member of the Board of Directors of the Portland Tax Forum. Mr. Brant has served as an adjunct professor, teaching corporate taxation, at Northwestern School of Law, Lewis and Clark College. He is an Expert Contributor to Thomson Reuters Checkpoint Catalyst. Mr. Brant is a Fellow in the American College of Tax Counsel. He publishes articles on numerous income tax issues, including Taxation of S Corporations, Reasonable Compensation, Circular 230, Worker Classification, IRC § 1031 Exchanges, Choice of Entity, Entity Tax Classification, and State and Local Taxation. Mr. Brant is a frequent lecturer at local, regional and national tax and business conferences for CPAs and attorneys. He was the 2015 Recipient of the Oregon State Bar Tax Section Award of Merit.

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