How A Drug Dealer Then Affects Marijuana Taxation Today

 

I spent substantial time last week reviewing and researching issues related to the marijuana industry. There is one Code section – Section 280E – that overpowers almost all tax planning in this area.

That section came into the Code in 1982.

It came in response to a Tax Court decision.

Let’s talk about it.

Here is the Court setting the table:

During …, petitioner Jeffrey Edmonson was self-employed in the trade or business of selling amphetamines, cocaine, and marijuana. His primary source of controlled substances was one Jerome Caby, who delivered the goods to petitioner in Minneapolis on consignment. Petitioner paid Caby after the drugs were sold. Petitioner received on consignment 1,100,000 amphetamine tablets, 100 pounds of marijuana, and 13 ounces of cocaine during the taxable year 1974. He had no beginning inventory of any of these goods and had an ending inventory of only 8 ounces of cocaine.

What got this bus in motion was a 1961 Supreme Court decision holding that everyone who made money – whether through legal or illegal activities – had to pay taxes on that money.

Edmonson got busted.

The IRS came in with a jeopardy assessment.

The IRS was concerned about Edmonson skipping, hence the jeopardy. This assessment causes all taxes, penalties, and interest to become immediately due. This allows to IRS to exercise its Collections powers (liens, levies, not answering phone calls for extreme durations) on an expedited basis.

Edmonson might not have been too concerned about po-po, but he wasn’t about to mess with the IRS. Although he did not keep books and records (obviously), he came up with a bunch of expenses to reduce his taxable income.

The IRS said: are you kidding me?

Off they went to Tax Court.

Edmonson went green eyeshade.

·      He calculated cost of goods sold for the amphetamines, marijuana, and cocaine

·      He calculated his business mileage

·      He had business trips and meals

·      He paid packing expenses

·      He had bought a small scale

·      He used a phone

·      He even deducted an office-in-home

The IRS, on the other hand, reduced his cost of goods sold and simply disallowed all other expenses.

The Court reduced or disallowed some expenses (it reduced his office in home, for example), but it allowed many others, including his cost of goods sold.

Here is the Court:

Petitioner asserts by his testimony that he had a cost of goods sold of $106,200. The nature of petitioner’s role in the drug market, together with his appearance and candor at trial, cause us to believe that he was honest, forthright, and candid in his reconstruction of the income and expenses from his illegal activities in the taxable year 1974.

The Edmonson decision revealed an unanticipated quirk in the tax Code. This did not go over well with Congress, which closed the Edmonson loophole by passing Code section 280E in 1982:

No deduction or credit shall be allowed for any amount 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.

This Code section pretty much disallows all business deductions (marijuana is classified as a controlled substance), except for cost of goods sold. Cost of goods sold is not considered a deduction in the tax Code; rather it is a subtraction from gross receipts to arrive at gross income. Think about a business where you could not deduct (most or all) your salaries, rent, utilities, taxes, insurance and so on. That is the headwind a marijuana business faces.

Meanwhile, things around us have changed greatly since 1982. Marijuana is legal in 21 states, and medical marijuana is legal in almost twice that number. Colorado by itself has collected over $2 billion in taxes since legalizing marijuana. There are publicly traded companies in the marijuana industry. There are even ETFs should you want to invest in this sector.

And that is how we have business activity that may be legal under state law but is illegal under federal law. The federal tax Code taps into federal law – that is, the Controlled Substances Act – and that tap activates Section 280E and its harsh tax result. 

Our case this time was Edmonson v Commissioner, T.C. Memo 1981-623.

Basis Basics

I am looking at a case involving a basis limitation.

Earlier today I accepted a meeting invite with a new (at least to me) client who may be the poster child for poor tax planning when it comes to basis.

Let’s talk about basis – more specifically, basis in a passthrough entity.

The classic passthrough entities are partnerships and S corporations. The “passthrough” modifier means that the entity (generally) does not pay its own tax. Rather it slices and dices its income, deductions and credits among its owners, and the owners include their slice in their own respective tax returns.

Make money and basis is an afterthought.

Lose money and basis becomes important.

Why?

Because you can deduct your share of passthrough losses only to the extent that you have basis in the passthrough.

How in the world can a passthrough have losses that you do not have basis in?

Easy: it borrows money.

The tax issue then becomes: can you count your share of the debt as additional basis?

And we have gotten to one of the mind-blowing areas of passthrough taxation.  Tax planners and advisors bent the rules so hard back in the days of old-fashioned tax shelters that we are still reeling from the effect.

Let’s start easy.

You and I form a partnership. We both put in $10 grand.

What is our basis?

                                     Me             You

         Cash                  10,000       10,000                  

 

The partnership buys an office condo for $500 grand. We put $20 grand down and take a mortgage for the rest.

What is our basis?

                                     Me             You

         Cash                  10,000       10,000                  

         Mortgage        240,000       240,000

                                250,000       250,000

So we can each have enough basis to deduct $250,000 of losses from this office condo. Hopefully that won’t be necessary. I would prefer to make a profit and just pay my tax, thank you.

Let’s change one thing.

Let’s make it an S corporation rather than partnership.

What is our basis?

                                     Me             You

         Cash               10,000        10,000                   

         Mortgage             -0-              -0-

                                10,000        10,000

Huh?

Welcome to tax law.

A partner in a general partnership gets to increase his/her basis by his/her allocable share of partnership debt. The rule can be different for LLC’s taxed as a partnership, but let’s not get out over our skis right now.       

When you and I are partners in a partnership, we get to add our share of the mortgage - $480,000 – to our basis.

S corporations tighten up that rule a lot. You and I get basis only for our direct loans to the S corporation. That mortgage is not a direct loan from us, so we do not get basis.

What does a tax planner do?

For one thing, he/she does not put an office condo in an S corporation if one expects it to throw off tax losses.

What if it has already happened?

I suppose you and I can throw cash into the S. I assure you my wife will not be happy with that sparkling tax planning gem.

I suppose we could refinance the mortgage in our own names rather than the corporate name.

That would be odd if you think about. We would have personal debt on a building we do not own personally.

Yeah, it is better not to go there.

The client meeting I mentioned earlier?

They took a partnership interest holding debt-laden real estate and put it inside an S corporation.

Problem: that debt doesn’t create basis to them in the S corporation. We have debt and no tax pop. Who advised this? Someone who should not work tax, I would say.

I am going to leverage our example to discuss what the Kohouts (our tax case this time) did that drew the Tax Court’s disapproval.               

Let’s go back to our S corporation. Let’s add a new fact: we owe someone $480,000. Mind you, you and I owe – not the S corporation. Whatever the transaction was, it has nothing to do with the S corporation.

We hatch the following plan.

We put in $240,000 each.

You: OK.

We then have the corporation pay the someone $480,000.

You: Hold up, won’t that reduce our basis when we cut the check?

Ahh, but we have the corporation call it a “loan” The corporation still has a $480,000 asset. Mind you, the asset is no longer cash. It is now a “loan.”  Wells Fargo and Fifth Third do it all the time.

You: Why would the corporation lend someone $480,000? Wells Fargo and Fifth Third are at least … well, banks.

You have to learn when to stop asking questions.

You: Are we going to have a delay between putting in the cash and paying - excuse me - “loaning” someone $480,000?

Nope. Same day, same time. Get it over with. Rip the band-aid.

You: Wouldn’t a Court have an issue with this if we get caught … errr … have the bad luck to get audited?

Segue to our court case.

In Kohout the Court considered a situation similar enough to our example. They dryly commented:

Courts evaluating a transaction for economic substance should exercise common sense …”

The Court said that all the money sloshing around could be construed as one economic transaction. As the money did not take even a breather in the S corporation, the Court refused to spot the Kohouts any increase in basis.

Our case this time was Kohout v Commissioner, T.C. Memo 2022-37.

No Shareholder, No S Corporation Election

 Our case this time takes us to Louisville.

There is a nonprofit called the Waterfront Development Corporation (WDC). It has existed since 1986, and its mission is to development, redevelop and revitalize certain industrial areas around the Ohio river downtown. I would probably shy away from getting involved - anticipating unceasing headaches from the city, Jefferson county and the Commonwealth of Kentucky - but I am glad that there are people who will lift that load.

One of those individuals was Clinton Deckard, who wanted to assist WDC financially, and to that effect he formed Waterfront Fashion Week Inc. (WFWI) in 2012. WFWI was going to organize and promote Waterfront Fashion Week – essentially a fundraiser for WDC.

Seems laudable.

Mr Deckard had been advised to form a nonprofit, on the presumption that a nonprofit would encourage people and businesses to contribute. He saw an attorney who organized WFWI as a nonprofit corporation under Kentucky statute.

Unfortunately, Waterfront Fashion Week failed to raise funds; in fact, it lost money. Mr Deckard wound up putting in more than $275,000 of his own money into WFWI to shore up the leaks. There was nothing to contribute to WDC.  What remained was a financial crater-in-the-ground of approximately $300 grand. Whereas WFWI had been organized as a nonprofit for state law purposes, it had not obtained tax-exempt status from the IRS. If it had, Mr Deckard could have gotten a tax-deductible donation for his generosity.

COMMENT: While we use the terms “nonprofit” and “tax-exempt” interchangeably at times, in this instance the technical difference is critical. WFWI was a nonprofit because it was a nonprofit corporation under state law. If it wanted to be tax-exempt, it had to keep going and obtain exempt status from the IRS.  One has to be organized under as a nonprofit for the IRS to consider tax-exempt status, but there also many more requirements.

No doubt Mr Deckard would have just written a check for $275 grand to WDC had he foreseen how this was going to turn out. WDC was tax-exempt, so he could have gotten a tax-deductible donation. As it was, he had ….

…. an idea. He tried something. WFWI had never applied for tax-exempt status with the IRS.

WFWI filed instead for S corporation status. Granted, it filed late, but there are procedures that a knowledgeable tax advisor can use. Mr Deckard signed the election as president of WFWI. An S election requires S corporation tax returns, which it filed. Mind you, the returns were late – the tax advisor would have to face off against near-certain IRS penalties - but it was better than nothing.

Why do this?

An S corporation generally does not pay tax. Rather it passes its income (or deductions) on to its shareholders who then include the income or deductions with their other income and deductions and then pay tax personally on the amalgamation

It was a clever move.

Except ….

Remember that the attorney organized WFWI as a nonprofit corporation under Kentucky statute.

So?

Under Kentucky law, a nonprofit corporation does not have shareholders.

And what does the tax Code require before electing S corporation status?

Mr Deckard has to be a shareholder in the S corporation.

He tried, he really did. He presented a number of arguments that he was the beneficial owner of WFWI, and that beneficial status was sufficient to allow  an S corporation election.

But a shareholder by definition would get to share in the profits or losses of the S corporation. Under Kentucky statute, Mr Deckard could NEVER participate in those profits or losses. Since he could never participate, he could never be a shareholder as intended by the tax Code. There was no shareholder, no S corporation election, no S corporation – none of that.

He struck out.

The sad thing is that it is doubtful whether WFWI needed to have organized as a nonprofit in the first place.

Why do I say that?

If you or I make a donation, we need a tax-exempt organization on the other side. The only way we can get some tax pop is as a donation.

A business has another option.

The payment could just be a trade or business expense.

Say that you have a restaurant downtown (obviously pre-COVID days). You send a check to a charitable event that will fill-up downtown for a good portion of the weekend. Is it a donation? Could be. It could also be just a promotion expense – there are going to be crowds downtown, you are downtown, people have to eat, and you happen to be conveniently located to the crowds. Is that payment more-than-50% promotion or more-than-50-% donation?

I think of generosity when I think of a donation. I think of return-on-investment when I think of promotion or business expenses.

What difference does it make? The more-than-50% promotion or business deduction does not require a tax-exempt on the other side. It is a business expense on its own power; it does not need an assist.

I cannot help but suspect that WFWI was primarily recruiting money from Louisville businesses. I also suspect that many if not most would have had a keen interest in downtown development and revitalization. Are we closer to our promotion example or our donation example?

Perhaps Mr Deckard never needed a nonprofit corporation.

When A Tax Shelter Blows Up

Can you image losing a tax case with the IRS and owing a billion dollars?

Who did this? We are talking about Dow Chemical Company (“Dow”). They lost in the District Court for the Middle District of Louisiana. I suppose they have no choice but to appeal. It is a billion dollars, after all.

What got them in this mess? 

A couple of tax shelters, one marketed by Goldman Sachs and both implemented by the law firm of King & Spalding. The IRS sued for tax years 1993 to 2003. 

Let’s talk about the first of the shelters – called a SLIP – which lasted from 1993 to 1997. Dow was not the only one that tried to SLIP the IRS. Merck and International Paper tried also.

SLIP stands for “Special Limited Investment Partnership.”  Its claim to fame was taking low-basis assets and turning them into tax deductions.  How would you do this? Well you could contribute them to a partnership, but that low basis would carryover. You would get no increased tax deduction by putting it a partnership.

Hmmm.

What if you put low-basis assets into a partnership and then leased them back?  Wait, the partnership would then have taxable income. Who would own the partnership? If you owned it, then the whole effort would be circular. 

What if there are other partners? Problem: you do not want other partners. 

What if you limit the other partners to a fixed return? It would be the same as paying interest to a bank, right? In partnership taxation we call this a priority or preference distribution. 

Problem: most of that income would be coming back to you. How can we solve this puzzle?

We delink the income distribution from the cash distribution. We bring in partners who will accept 6 or 7 percent priority, and we allocate virtually all the income to them.

Now why would someone agree to this?

If someone doesn’t pay U.S. tax, that’s why. Someone like a foreign bank.

Eureka!

You offer a foreign bank the deal, now referred to as a “structured financial transaction.” This means that it is complicated, and you will be paying top dollar for investment, legal and accounting advice. You explain to the bank that it would:

·        Receive a significant premium over a corporate bond

·        Take on less credit risk than a corporate bond

·        Escape any U.S. tax

Sure enough, Dow and Goldman Sachs rounded up five foreign banks willing to contribute $200 million. Dow set up a maze of subsidiaries, into which it dumped 73 patents. The interesting fact about these patents is that Dow had amortized them virtually to zero, Dow still used them in current operations and retained enough of the processes to make it unlikely anyone would want to buy the patents, though.  The patents appraised at $867 million.

One of those Dow subs contributed the patents into a partnership called Chemtech I, taking back an 81 percent ownership.

Dow paid Chemtech I around $143 million for use of the patents.

Chemtech I paid the foreign banks 7 percent as their priority return. Since the banks had invested $200 million, this was a cool $14 million in their pockets. Chemtech I paid a couple of other things, took the remaining cash and put in a subsidiary. That subsidiary loaned the money back to Dow. How much cash did it loan back, you ask? About $136 million. For one year.

On its tax return Chemtech I reported approximately $122 million in income. It allocated $115 million of that to the banks. Only $28 million in income went back to Dow itself.

What we have just talked about is known in tax lingo as a “strip.”

And there is the SLIP. All Dow did was move money around. It paid the foreign banks $14 million in interest but called it a priority, thereby dragging over $115 million of income with it. As the banks did not pay U.S. tax, they did not care. Dow however did.

In 1997 there was a change in U.S. tax law, and Dow had to switch to another tax strategy. Dow wanted to cash out the banks and start something else.

The banks wanted their share of the market value of those patents on the way out. Seems fair, as they were “partners” and all. Dow said “no way”. The partnership agreement stipulated how the patents were to be valued and how to calculate the banks’ share. Dow paid the banks approximately $8 million. The banks complained, but to no avail. Dow controlled the calculation of value.

Once the banks were out of the way, Dow created a second tax shelter using a fully-depreciated chemical plant in Louisiana. This strategy did not require banks, but it did employ a very clever maneuver to pump-up the basis of the plant, thereby creating depreciation deductions that Dow could use to offset real income from other sources.

Oh, there was a formidable tax issue that Dow resolved by ripping up a piece of paper and replacing it with another.

OBSERVATION: And there you see the IRS’ frustration: Dow is not dealing with independent parties. In Chemtech I, it was dealing with banks acting as banks. Dow called them partners, but it may as well have called them peanut –butter sandwiches for the difference it made. In the second deal (called Chemtech II), Dow did not even leave the ranch. It replaced a deal between its subsidiaries with another deal between its subsidiaries. Really?  No wonder the IRS was hot around the ears.

So the IRS gets into Dow’s tax returns. In 2005 it issued a Notice of Final Partnership Administrative Adjustment for tax years 1993 and 1994. Dow responds that the IRS did not give the notice to the properly designated person – the Tax Matters Partner – and the notice was therefore invalid.

OBSERVATION: The tax matters partner rule is to protect both the partnership and the IRS. It means something when you have big partnerships with hundreds if not thousands of partners. Dow however was setting up partnerships like they were jellybeans. I find it cheeky – to be polite – that Dow’s defense was “you sent the mail to the wrong cubicle.”

This thing goes back and forth like a tennis match. In the end, a court has to decide. The IRS had scooped up additional years – through 2003 – by the time this was resolved.

How would the IRS attack the shelters?

There are a couple of ways. The first is the “economic substance” doctrine. Think of it as the tax equivalent of “where’s the beef?” The court looks at the transactions and determines if there is any reality to what supposedly is going on. There are three prongs to this test:

(1) Does the transaction have economic substance compelled by business or regulatory realties;

(2) Does the transaction have tax-independent considerations; and

(3)  Is the transaction not designed in toto with tax avoidance intent?

The Court looks at the SLIPS and observes the obvious:

(1) The SLIPs did not change Dow’s financial position in any way. Chemtech I could not have licensed those patents to a third party if it wanted to, as it did not own all the rights. This means that Chemtech I could not produce independent revenue. That is a problem.

(2) The cash flow was circular. The little bit that left (to the banks) was the equivalent of interest. Big problem.

(3) Dow argued that it was preserving its credit rating and borrowing power, but it could not prove any increase in its credit rating or borrowing power. Dow also stumbled explaining why it structured the transaction this way rather than another way – like having domestic banks in Chemtech I.

The second way the IRS attacked was by arguing the partnership was a sham. This argument is slightly different from “economic substance,” as that argument looks at transactions. The sham partnership argument looks at the partnership itself and asks: is this a real partnership?

The Court notes the following:

·        The banks got a priority of 7%.

·        The only room left for the banks to profit was if the patents went up in value. The banks were only allocated 1% of that number, and Dow controlled how to calculate the number.

·        When the banks complained about their lousy 1%, a Dow executive called them “greedy.”

OBSERVATION: It was clear the Court was not impressed with this executive’s comment.

·        It was virtually impossible for the banks to lose money.

·        The one risk to the banks – IRS challenge – was indemnified by Dow.

The Court observed that true partners have the risk of loss and the hope of gain. The banks had virtually no risk of loss and sharply limited room for gain. There may have been a banking relationship, but there was no more a partnership here than in a Kardashian marriage.

The Court said the shelters were bogus and Dow owed the tax.

And a 20 percent penalty to boot.

MY TAKE:  Those who know me, or who follow this blog, know that I generally side with the taxpayer. After all, it is the taxpayer who sets an alarm clock, takes on a mortgage or builds a website that actually works, whereas the government is little more than weight in the trunk.

Still, at least pretend that there is some business reason for all the tax fireworks that are going off.

This court opinion is 74 pages long. While I am somewhat impressed with the tax wizardry that Dow brought to bear, I must admit that I am reading tax planning for its own sake. That may groove someone like me, but that is not enough to pass muster. There has to be a business purpose for moving all the pieces around the board, otherwise the IRS can challenge your best-laid plans.

The IRS challenged Dow. 

Dow lost.