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Big catAs discussed in recent blog posts, the Oregon Legislative Assembly recently enacted a Corporate Activity Tax (“CAT”). Governor Kate Brown signed the legislation into law, effective January 1, 2020. Put in simplest terms, the CAT is a gross receipts tax on businesses with greater than $1 million of “commercial activity sourced to this state.”

Given the broadness of the new law and the many anticipated difficulties that taxpayers, tax advisors and the government will likely encounter determining what constitutes “commercial activity sourced to this state,” the need for the Oregon Department of Revenue (the “Department”) to adopt administrative rules on the new law is evident.

sailboat in stormAs we reported in our June 4 blog post, Oregon lawmakers had recently enacted a “corporate activity tax” (“CAT”) that applies to certain Oregon businesses. The new law, absent challenge, becomes effective January 1, 2020.

We also recently reported that a prominent group of Oregon businesses planned to challenge the CAT. It appears, however, that the momentum for a challenge has recently died.

In this blog post, we discuss the reasons causing the death of the challenge. In addition, we cover some technical changes in the new law that are currently awaiting Governor Kate Brown’s signature.

Capitol in Salem, OregonWe are taking a break from our multi-post coverage of Opportunity Zones to address a recent, significant piece of Oregon tax legislation. 

On May 16, 2019, Governor Kate Brown signed into law legislation imposing a new “corporate activity tax” (“CAT”) on certain Oregon businesses.  The new law expressly provides that the tax revenue generated from the legislation will be used to fund public school education. 

Although the new tax is called a “corporate” activity tax, it is imposed on individuals, corporations, and numerous other business entities.  The CAT applies for tax years beginning on or after January 1, 2020. 

To help defray the expected increased costs of goods and services purchased from taxpayers subject to the CAT that will assuredly be passed along to consumers, the Oregon Legislative Assembly modestly reduced personal income tax rates at the lower income brackets.


M&A dealThe Tax Cuts and Jobs Act (“TCJA”) will significantly impact merger and acquisition (“M&A”) activity. Although billed as tax reform, the TCJA did not reform or simplify the Internal Revenue Code (“Code”).

Virtually none of the provisions of the TCJA directly impact M&A transactions. Rather, the TCJA added or modified several sections of the Code that indirectly impact transaction structuring, pricing, negotiations and due diligence. Making matters more complex, some of these provisions of the TCJA are temporary.

This blog post briefly highlights several key provisions of the TCJA and the impact on M&A.

ConfettiAs reported in my November 2015 blog post, in accordance with Internal Revenue Code (“Code”) Section 280E, taxpayers (for purposes of computing federal taxable income) are prohibited from deducting expenses related to the production, processing or sale of illegal drugs, including marijuana.

A Bit of Welcome Relief?

Measure 91, officially called the Control, Regulation, and Taxation of Marijuana and Industrial Hemp Act, passed by Oregon voters, appears to have alleviated some of the impact of Code Section 280E as it relates to Oregon taxable income. Specifically:

  1. Section 71 of Measure 91 provides that Code Section 280E does not apply for purposes of determining Oregon taxable income or loss under our corporate income tax regime. This provision sets forth no specific effective date. So, in accordance with Sections 81 and 82 of Measure 91, it became effective on July 1, 2015.
  2. Section 74 of Measure 91 provides that Code Section 280E does not apply for purposes of determining Oregon taxable income or loss under our individual income tax regime. This provision of Measure 91 specifically provides that the change became effective for tax years beginning on or after January 1, 2015.

So, following the passage of Measure 91, were there any Oregon tax problems plaguing the cannibals industry? The short answer is: Maybe.

Measure 91 generally only applies to the recreational marijuana industry. Even though nothing in Measure 91 says Sections 71 and 74 are limited to recreational marijuana, maybe an argument could be made that these provisions did nothing to alleviate the Code Section 280E issue for medical marijuana business activities.

Don’t despair; Oregon lawmakers came to the rescue. The law is now clear (at least as clear as a law can be) that, with respect to the Oregon individual income tax regime, folks in both medical and recreational marijuana businesses may deduct (for Oregon purposes only) expenses that would be otherwise be nondeductible under Code Section 280E.

House Bill 4014 Is Signed Into Law

On March 3, 2016, Oregon Governor Kate Brown signed House Bill 4014 into law. The bill, which spans numerous pages, deals with several issues related to the Oregon cannabis industry, including the application of Code Section 280E to both the recreational and the medical marijuana industries.

The provisions of House Bill 4014 relating to Oregon income taxation are contained in: Sections 28, 28a and 29.

SECTION 28 of House Bill 4014 amends ORS 316.680 by adding subsection (i) providing that there shall be subtracted from federal taxable income:

“Any federal deduction that the taxpayer would have been allowed for the production, processing or sale of marijuana items authorized under ORS 475B.010 to 475B.395 but for section 280E of the Internal Revenue Code.”

SECTION 28a of House Bill 4014 amends ORS 316.680 by adding subsection (i) providing that there shall be subtracted from federal taxable income:

“Any federal deduction that the taxpayer would have been allowed for the production, processing or sale of marijuana items authorized under ORS 475B.010 to 475B.395 or 475B.395 or 475B.400 to 475B.525 but for section 280E of the Internal Revenue Code.”

SECTION 29 of House Bill 4014 provides that the amendments to ORS 316.680 by Section 28 apply to conduct occurring on or after July 1, 2015 but before January 1, 2016, and to tax years ending before January 1, 2016. The amendments to ORS 316.680 by section 28a apply to conduct occurring on or after January 1, 2016, and to tax years beginning on or after January 1, 2016.

Implications for the Oregon Cannabis Industry

What this means for the cannabis industry in Oregon is twofold:

  1. For Oregon personal income tax purposes only (for tax years beginning on or after July 1, 2015 but before January 1, 2016), the prohibition contained in Code Section 280E does not apply to the non-medical production, processing or sale of marijuana. In other words, a subtraction from Oregon personal income tax is permitted by folks in a recreational marijuana business for any federal deduction a taxpayer would have been allowed for expenses related to the production, processing or sale of marijuana had there been no prohibition under Code Section 280E.
  2. For Oregon personal income tax purposes only (for tax years beginning on or after January 1, 2016), the prohibition contained in Code Section 280E does not apply to the production, processing or sale of marijuana (medical and non-medical marijuana).  In other words, on or after January 1 of this year a subtraction from Oregon personal income tax is permitted by folks in both a medical and recreational marijuana business for any federal deduction a taxpayer would have been allowed for expenses related to the production, processing or sale of marijuana had there been no prohibition under Code Section 280E.

Interestingly, House Bill 4014 does not appear to address the Oregon corporate excise or income tax regimes. Remember, Section 71 of Measure 91 clearly tells us that, after July 1, 2015, Code Section 280E does not apply to the computation of Oregon corporate taxable income.

Why did Oregon lawmakers feel the need to make it clear that Code Section 280E does not apply to the computation of Oregon individual taxable income in the case of both medical and recreational marijuana business activities (as of January 1, 2016), but did not do the same for the computation of Oregon corporate taxable income?

Oregon law clearly contemplates corporations and other entities will be used to operate marijuana related businesses. In fact, both Measure 91 and the Oregon regulations governing the local marijuana industry allow businesses to be organized as corporations (and other entities). The definition of "person" in Measure 91 includes corporations (Section 5(24)), and various parts of the regulations contemplate that marijuana licenses will be issued to corporations and other entities (e.g., OAR 845-025-1045(3).

Was this apparent omission intentional or simply as oversight by Oregon lawmakers? It certainly seems Measure 91 covers (for purposes of Code Section 280E) recreational and medical marijuana activities at both the Oregon corporate and individual income tax levels. Was House Bill 4014 necessary to clarify the elimination of the application of Code Section 280E for Oregon income tax purposes?

It will be interesting to see how the Oregon Department of Revenue interprets House Bill 4014 and Measure 91 in this regard. Time will tell.

An Observation

One interesting observation about Measure 91 is that the clear language eliminating the application of Code Section 280E for Oregon individual and corporate taxation is not expressly limited to marijuana activities. Arguably, it eliminated the application of Code Section 280E for Oregon income tax purposes in all instances (including the sale or distribution of illegal drugs). It appears House Bill 4014 removes that interpretation of the law in the instance of the Oregon individual tax regime as it expressly limits the application to marijuana, but its silence as to the Oregon corporate tax regime leaves that interpretation alive. I hope this was not the legislature’s intent.

As a general rule, in accordance with IRC § 162(a), taxpayers are allowed to deduct, for federal income tax purposes, all of the ordinary and necessary expenses they paid or incurred during the taxable year in carrying on a trade or business.  There are, however, numerous exceptions to this general rule.  One exception is found in IRC § 280E.  It provides:

“No deduction or credit shall be allowed for any payment paid or incurred during the taxable year in carrying on any trade or business if such trade or business (or the activities which comprise such trade or business) consists of trafficking in controlled substances (within the meaning of schedule I and II of the Controlled Substances Act) which is prohibited by Federal law or the law of any state in which such trade or business is conducted.”

Marijuana-plant-300x200Congress enacted IRC § 280E as part of the Tax Equity and Fiscal Responsibility Act of 1982, in part, to support the government’s campaign to curb illegal drug trafficking.  Even though several states have now legalized medical and/or recreational marijuana, IRC § 280E may come into play.  The sale or distribution of marijuana is still a crime under federal law.  The impact of IRC § 280E is to limit the taxpayer’s business deductions to the cost of goods sold.

On October 22, 2015, the U.S. Tax Court issued its opinion in Canna Care, Inc. v. Commissioner, T.C. Memo 2015-206.  In that case, Judge Haines was presented with a California taxpayer that is in the business of selling medical marijuana, an activity that is legal under California law.

The facts of this case are interesting.  Bryan and Lanette Davies, facing significant financial setbacks and hefty educational costs for their six (6) children, turned to faith for a solution.  After “much prayer,” Mr. Davies concluded that God wanted him to start a medical marijuana business.  Unfortunately, it does not appear that he consulted with God or a qualified tax advisor about the tax implications of this new business before he and his wife embarked upon the activity.

The good news for the Davies is that their business blossomed.  In fact, they employ ten (10) people in the business and have enjoyed financial success.  They timely filed state and federal income tax returns, reported income and paid, what they believed, was the proper amount of taxes.  The bad news for the Davies is the fact that the IRS did not agree with their computation of the tax liability.

The IRS issued a notice of deficiency.  Not able to resolve the matter at IRS appeals, the Davies found themselves in the U.S. Tax Court.  The sole issue in the case was whether the taxpayers’ business deductions were properly disallowed by the Service under IRC § 280E.

To no avail, the Davies presented numerous arguments as to why marijuana should no longer be a controlled schedule I substance.  They also asserted that their new business created employment opportunities for others, cured their family’s financial woes, and allowed them to participate in civic and charitable activities.

Judge Haines quickly dismissed the Davies’ arguments, concluding the sale of marijuana is prohibited under federal law—marijuana is a schedule I controlled substance.  Accordingly, IRC § 280E prevents taxpayers from deducting the expenses incurred in connection with such activity (other than the cost of goods sold).

Faced with a tax assessment exceeding $800,000, the Davies argued that their business does more than sell marijuana.  In fact, it sells books, shirts and other items related to medical marijuana.  Citing other cases, they argued that their expenses should be apportioned among the various activities (i.e., the sale of medical marijuana and the sale of other items), and that they should be able to deduct the expenses related to the sale of the non-marijuana items.

The court explained that, where a taxpayer is involved in more than one distinct trade or business, it may be able to apportion its ordinary, necessary and reasonable expenses among the different trades or businesses.  Unfortunately for the Davies, they could not show that they operated two (2) or more trades or businesses.  In this case, the facts indicated that the sale of shirts, books and other items was merely incidental to the sale of medical marijuana.  There was not more than one (1) trade or business.

PRACTICE ALERT:  Whether more than one (1) trade or business exists is a question of facts and circumstances.  Under CHAMP v. Commissioner, 128 T.C. 182 (2007), if a taxpayer operates more than one (1) distinct trade or business, it may be allowed to apportion its expenses among the trades or businesses.  If only one (1) of the businesses is impacted by IRC § 280E, only the expenses relating thereto should be denied.  The key is establishing that more than one (1) trade or business exists, and reasonably be able to apportion the expenses among those trades or businesses.  Keeping separate books and records, and accounting for business expenses in a separate manner, is likely the best approach.  The more separation and distinction among the businesses the better the chances of showing more than one (1) trade or business exists.  Maintaining separate entities or business names for each activity may be warranted.

The Davies lost the case and are now faced with a hefty tax bill.  Unless IRC § 280E is amended, taxpayers involved in the sale of medical and/or recreational marijuana, despite state legalization, will be presented with the same dilemma faced by the Davies in Canna Care, Inc. v. Commissioner.

I would like to invite you to NYU 74th Institute on Federal Taxation taking place in New York, New York on October 25-30, 2015, and in San Francisco, California on November 15-20, 2015.

The NYU Tax Institute is one of our country’s most pre-eminent tax conferences for CPAs and attorneys. I am proud to be a presenter on the closely-held business panel of the program on Oct. 29 and Nov. 19. This is my third time speaking at the Institute. This year, I will present a newly-written white paper on qualified subchapter S subsidiaries.

As in the past years, the Institute will cover a broad spectrum of tax topics, including tax controversy, executive compensation and employee benefits, international taxation, corporate taxation, real estate taxation, partnership taxation, taxation of closely-held businesses, trusts and estate, and ethics. What’s nice about the Institute is that you can pick and choose what sessions you’d like to attend in order to best meet your practice needs.

I hope you can join us this year in either New York or San Francisco. I am confident you will find the topic coverage and the faculty to be fabulous!

Click here to see the complete brochure and registration information: NYU 74th IFT Registration



Barnes v. Commissioner, 712 F.3d 581 (D.C. Cir. 2013) aff’g T.C.M. 2012-80 (2012) is illustrative of the point that understanding the basis adjustment rules is vital.

If this case was made into a movie, the name of the movie would tell the entire story – S corporation shareholders are not allowed to just make up the basis adjustment rules!  Also, as I have repeatedly stated, poor records lead to disastrous results.  The DC Circuit affirmed the US Tax Court in April of 2013 to finally put an end to the case.

Marc and Anne Barnes, husband and wife, are entrepreneurs.  They were engaged in several businesses, including restaurants, nightclubs and entertainment promotion.  These businesses were operated through a sole proprietorship and several entities they owned 100% of, including two S corporations and a C corporation.

The tax returns at issue were the 2003 returns.  One of the Barnes’ S corporations was Whitney Restaurants, Inc. which operated a Washington DC restaurant and nightclub called Republic Gardens (Whitney has since sold Republic Gardens).  Upon audit of the Barnes’ 2003 tax return, the Service pulled in the 1120S of Whitney Restaurants.

In addition to some smaller items, the Service disallowed a $123,006 loss stemming from Whitney on the ground the Barnes’ had insufficient basis to take the losses.  In addition, the Service assessed an IRC Section 6662 accuracy related penalty and an IRC Section 6651 late filing penalty.

The Barnes’ contested the assessment, including the penalties, and filed a petition in the US Tax Court.  Prior to the court’s ruling, however, they conceded liability for the late filing penalty.  The return was eight months late.  So, the Court was left to decide whether the assessment of taxes and the accuracy related penalty were appropriate.

The facts are a little convoluted.  In 1995, the Barnes’ had a $22,282 loss from Whitney, suspended due to lack of basis.  On their 1996 joint return, they reported the $22,282 loss even though their 1996 K-1 showed an additional $136,229 loss for the tax year.  In 1997, they contributed $278,000 in capital to Whitney, enabling them to finally take the suspended losses from 1995 and 1996, which totaled $158,511, but in fact they only deducted the current 1997 loss of $52,594 on the 1997 return.  USER ERROR!

To follow the story, we must fast forward to 2003.  The taxpayers awake from the sleep they were in and with the help of a new accountant, they determine they should have deducted the losses on the 1997 return.   Guess what; that year is closed.  Ouch!

Sounds bad; but, the Barnes’ find a way to relieve some of the pain.  They claim, since they did not use the basis for the losses from 1995 and 1996, they can take a deduction for the losses resulting from the current year on the current return – tax year 2003 -- using the unused basis from 1997.  They make three arguments in favor of this position:

First, they argue IRC Section 1367(a)(2)(B) only requires you to reduce basis for losses you actually report on your return.  So, since they did not take the losses on the 1997 return, there should be no reduction in basis.  WRONG!

IRC Section 1367(a)(2)(B) requires an S corporation shareholder to reduce stock basis by any losses that a shareholder should have taken into account under IRC Section 1366(a)(1)(A), even if the shareholder did not actually claim the benefit of the pass-through of the losses on his/her return.

Next, the Barnes’ argued the tax benefit rule allowed them to claim a deduction in 2003 for the loss they should have deducted in 1997.  WRONG AGAIN!

The tax benefit rule generally only applies when taxpayers recover amounts they deducted in a prior year.  When that situation arises, the taxpayer may exclude the recovered income to the extent the prior deduction did not give rise to a tax benefit.  The tax benefit was inapplicable in the Barnes case.

Last, the Barnes argued that their failure to properly deduct the losses in 1997 caused them to compute an incorrect amount of losses that could be used to offset income in 2003.  I do not understand the argument.  It makes no sense.  Guess what, the Tax Court did not understand it either.  The Barnes’ lose the battle!

The Barnes’ do not go down for the count.  Instead, they turn on their CPA and claim they relied upon professional advice.  So, no penalties for accuracy or negligence are appropriate.  Unfortunately, the court concluded they did not provide evidence to show they acted in good faith in relying upon professional advice. In fact, the evidence showed the accounting firm’s advice was limited by the Barnes’ inadequate accounting records and erroneous basis information from prior years in which it did not represent the taxpayers.

The result is simple:  The Barnes’ were stuck with the tax and penalty assessment and a boat load of interest as the case muddled through the IRS and the court system for over nine years.

There are two pearls of wisdom to take away from the case:

  1. You reduce stock basis by the losses allowable under IRC Section 1366 even if you fail to report the losses on your return; and
  2. If a taxpayer does not provide you with adequate records, they will not likely prevail in a dispute over negligence or accuracy related penalties.

CPAs and other tax advisors need to be careful.  You want to resist the temptation to represent or continue to represent clients that do not maintain adequate records.

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 Brant

Larry J. Brant is a Shareholder in Garvey Schubert Barer, a law firm based out of the Pacific Northwest, with offices in Seattle, Washington; Portland, Oregon; New York, New York; Washington, D.C.; 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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