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Sunday, July 19, 2020

No Required Minimum Distributions For 2020


There is a tax deadline coming up. It may matter to those who are taking required minimum distributions (MRDs) from your IRAs and certain employer-based plans.

You may recall that there is a trigger concerning retirement plans when one reaches age 72.
COMMENT: The trigger used to be age 70 ½ for tax years before 2020.
The trigger is – with some exception for employer-based plans – that one has to start withdrawing from his/her retirement account. There are even IRS-provided tables, into which one can insert one’s age and obtain a factor to calculate a required minimum distribution.
COMMENT: There are severe penalties for not withdrawing a minimum distribution. Fortunately, the IRS is fairly lenient in allowing one to “catch-up” and avoid those penalties. At 50% of the required distribution, the MRD penalty rate is one of the most severe in the tax Code.
Let’s say that you are in the age range for MRDs. You have, in fact, been taking monthly MRDs this far into 2020.

There has been a law change: you can take 2020 distributions if you wish, but distributions are not mandatory or otherwise required. That is, there are no MRDs for 2020. This means that you can take less than the otherwise-table-calculated amount (including none, if you wish) and not taunt that 50% penalty.

Why the change in tax law?

The change is related to the severe economic contractions emanating from COVID and its associated lockdowns and stay-at-home restrictions. Congress realized that there was little financial sense in forcing one to sell stocks and securities into a bear market to raise the cash necessary to pay oneself MRDs.

Hot on the heels of the change is the fact that different people take MRDs at different times. Some people take the distribution early in the year, others late, and yet others take distributions monthly or quarterly. There is no wrong answer; it just depends on one’s cash flow needs.

Let’s take the example we started with: monthly distributions.

Well, it’s fine and dandy that I do not have to take any more distributions, but what about the amount I took in January -before the law change? And February – before …., well, you get the point.

You can put the money back into the IRA or retirement account.

Think of it as a mulligan.

But you have to do this by a certain date: August 31, 2020.

You have approximately another month to get it done.

Here are some questions you may have:

(1)  Does this change apply to 401(k)s, 403(b)s, 457(b)s?

Answer: Yes.

(2)  How about inherited accounts?

Answer: Yes. You have to put it back in the same (that is, the inherited) account, of course.

(3)  What if I was having taxes withheld?

Answer: You are going to have reach into your pocketbook temporarily. Say that you took a $25,000 distribution with 20% federal withholding. You never spent any of it, so you have $20,000 sitting in your bank account. If you want to unwind the entire transaction, you are going to have to take $5,000 from somewhere, add it to the $20,000 you already have and put $25,000 back into your IRA or retirement account.

You may wonder what happened to the $5 grand that was withheld. It will be refunded to you – when you file your 2020 tax return.

(4)  Continuing with Example (3): what if I don’t have the $5 grand?

Answer: Then put back the $20,000 you do have. It’s not 100%, but you put back most of it. You will have that gigantic withholding when you finally file your 2020 taxes.

(5)  What if I turned 70 ½ last year (2019) and HAVE TO take a MRD in 2020?

Answer: The answer may surprise you. The downside to waiting is that you would (normally) have to take a distribution for 2019 (you turned 70 ½, after all) and another for 2020 itself. This means that you are taking two MRDs in one tax year. Under the new 2020 tax law, you do not have to take EITHER (2019 or 2020) distribution. Your first distribution would be in 2021, and you would have had no distributions for 2019 or 2020.

(6)  Does this change apply to pensions?

Answer: No. Pensions are “defined benefit” plans, whereas IRAs, 401(k)s and so on are “defined contribution” plans. The change is only for defined contribution plans.

(7)  Does this change apply to Roths?

Answer: Roths do not have minimum required distributions, so this law change means bupkis to them.

(8)  What if I went the other way: I withdrew from my traditional IRA and would like to put it back as a Roth?

Answer: Normally one cannot do this, as MRDs do not qualify for a Roth conversion. With no MRDs for 2020, however, you have a one-time opportunity to flip some of your traditional IRA into a Roth. Remember that you will have to pay tax on this, though.  

(9)  How does this law change interact with the qualified charitable distribution rules?

Answer: A qualified charitable distribution (QCD) is when you have your IRA custodian issue a check directly to a charity. You do not get a deduction for the contribution, but the upside is that you do not have to report the distribution as income. If you do not itemize deductions, this technique is – by far – the most tax-efficient way to go. The QCD rules are independent of the MRD 2020 rule change. If you want to donate via charitable distributions in 2020, then go for it!

If you are already into your MRD for 2020 and do not need the money – some or all of it – remember that you have approximately another month to put it back.


Saturday, July 18, 2020

An Expiring Six Figure Tax Refund


We had an unusual client situation this 2020 tax-season-that-refuses-to-go-away.

It involved a high earner and a private plane.

More specifically, buying a private plane.

The high earner bought the plane in 2016, which meant there was a dollar-for-dollar depreciation deduction if the plane was successfully placed in business use. While that may sound simple enough, there is a high wall in the tax Code (specifically, Section 280F(d)(6)(C)(ii)) that one has to scale. The IRS is onto wealthy taxpayers buying a plane for “business” use, using it also for personal reasons and reporting relatively minimal income for that personal use under the SIFL rules.
COMMENT: Think of the SIFL rules as picking up mileage-rate income for your personal use of a company car.
It took a while to resolve the issues involved in this return. We prepared and the client filed his 2016 return in 2020. We filed on paper, as it was too late to electronically file. Going into COVID, mind you, when soon there would be no one at the IRS to open the mail. In fact, at one point the IRS estimated that it had over 10 million pieces of unopened mail to process.

Not the best-case scenario, but I was not immediately concerned.

Until our client received an IRS letter that the period for claiming a 2016 tax refund was about to expire.

That amount was six figures.

Let’s talk about the tax statute of limitations.

There are different sides to the statute of limitations.

In general, we know that there is a three-year statute for the IRS to look at one’s return. If you filed, for example, your 2016 tax return on April 15, 2017, the IRS has until April 15, 2020 (barring unusual circumstances) to look at and change your return.

The technical term for any additional taxes is “assessment”, and the IRS has 10 years to collect any taxes assessed. You there have a second limitations period.

But what if the IRS owes you?

Let’s say that you have a refund for 2016. You are in no hurry to file, because there is nothing for the IRS to chase down. You have a refund, after all.

That three-year statute flips and can now be your enemy.

You have to claim that refund within three years.

What if you don’t?

Then you lose it.

You had better file that 2016 tax return by April 15, 2020.

Let’s go tax nerd here.

Technically, there are two limitations periods running concurrently. You have to meet both of them to get to your refund.

(1)  You have to file a refund claim within three years of filing the return.

There is some technical mumbo-jumbo here. Since you never filed a return, the filing serves as both a return and a claim (for refund). You would easily meet the three-year test as filing the return also counts as filing a claim. You did both at the same time.

That, however, is not the problem.

(2)   Taxes paid within the preceding three-year period are recoverable.

The taxes for 2016 were considered paid-in as of April 15, 2017 (when the return was due). As long as you get that return/claim in by April 15, 2020, you are good, right?

Who was not working on April 15, 2020?

The IRS, that‘s who.

Nor many CPA firms. If CPAs were working, odds are they were working in a diminished capacity.  

Still, our return was filed before April 15, 2020, so was there need to be concerned that it was sitting in a trailer with millions of other returns?

And didn’t many deadlines got extended to July 15, in any event?

That answer is fine until the client begins to panic. Did the period run out on April 15? Is the period running out on July 15? ARE YOU SURE?

My partner was anxious: should we call the IRS? Should we file another claim? Should we request an extension of the statute?

Ixnay on that last one, champ.

We had one more card to play.

Guess what extends the three-year lookback period for recoverable taxes?

An extension, that’s what, and our client had one for 2016.

No matter what, our client’s lookback period for taxes goes through October 15, 2020. The client has three years and six months to get to those taxes.

I am, by the way, a fan of routine extensions for tax returns of complexity. COVID has given me another reason why.

Happy client.

Crazy year.

Sunday, July 5, 2020

Requesting A Payment Plan With Over $7 Million In The Bank


Sometimes I wonder how people get themselves into situations.

Let’s take a look at a recent Tax Court case. It does not break new ground, but it does remind us that – sometimes – you need common sense when dealing with the IRS.

The Strashny’s filed their 2017 tax return on time but did not pay the tax due.
COMMENT: In and of itself, that does not concern me. The penalty for failing to file a tax return is 10 ten times more severe than filing but not paying. If the Strashny’s were my client and had no money, I would have advised the same.
The 2017 return had tax due, including interest, of over $1.1 million.
COMMENT: Where did the money go? I am curious now.
In June, 2018 the IRS assessed the tax along with a failure-to-pay penalty.

In July, 2018 the Strashny’s sent an installment payment request. Because of the amount of money involved, they had to disclose personal financial information (Form 433-A). They wanted to stretch the payments over 72 months.
COMMENT: Standard procedure so far.
Meanwhile the IRS sent out a Notice of Intent to Levy letter (CP90), which seemed to have upset the Strashny’s.

A collection appeal goes before an IRS officer settlement officer (or “SO,” in this context). In April, 2019 she sent a letter requesting a conference in May.
COMMENT: Notice the lapsed time – July, 2018 to April, 2019. Yep, it takes that long. It also explains while the IRS sent that CP90 (Notice of Intent to Levy): they know the process is going to take a while.
The taxpayers sent and the SO received a copy of their 2018 tax return. They showed wages of over $200,000.

OK, so they had cash flow.

All that personal financial information they had sent earlier showed cryptocurrency holdings of over $7 million. Heck, they were even drawing over $19,000 per month on the account.

More cash flow.
COMMENT: Folks, there are technical issues in this case, such as checking or not checking a certain box when requesting a collection hearing. I am a tax nerd, so I get it. However, all that is side noise. Just about anyone is going to look at you skeptically if you cite cash issues when you have $7 million in the bank.
The SO said no to the payment plan.

The Strashny’s petitioned the Tax Court.
COMMENT: Notice that this case does not deal with tax law. It deals, rather, with tax procedure. Procedure established by the IRS to deal with the day-to-day of tax administration. There is a very difficult standard that a taxpayer has to meet in cases like this: the taxpayer has to show that the IRS abused its authority.
The Strashny’s apparently thought that the IRS had to approve their request for a payment plan.

The Court made short work of the matter. It reasoned that the IRS has (with limited exceptions) the right to accept or reject a payment plan. To bring some predictability to the process, the IRS has published criteria for its decision process. For example, economic hardship, ill health, old age and so on are all fair considerations when reviewing a payment plan.

What is not fair consideration is a taxpayer’s refusal to liquidate an asset.

Mind you, we are not talking a house (you have to live somewhere) or a car (you have to get to work). There are criteria for those. We are talking about an investment portfolio worth over $7 million.

The Court agreed with the IRS SO.

So do I.

Was there middle ground? Yes, I think so. Perhaps the Strashny’s could have gotten 12 or 24 months, citing the market swings of cryptocurrency and their concern with initiating a downward price run. Perhaps there was margin on the account, so they had to be mindful of paying off debt as they liquidated positions. Maybe the portfolio was pledged on some other debt – such as business debt – and its rash liquidation would have triggered negative consequences. That approach would have, however, required common sense – and perhaps a drop of empathy for the person on the other side of the table – traits not immediately apparent here.

They got greedy. They got nothing.

Our case this time was Strashny v Commissioner.

Sunday, June 28, 2020

This Is Why We Cannot Have Nice Things


I am looking at a case involving a conservation easement.

We have talked about easements before. There is nothing innately sinister about them, but unfortunately they have caught the eye of people who have … stretched them beyond recognition.

I’ll give you an example of an easement:

·      You own land in a bucolic setting.
·      It is your intention to never part with the land.
·      It is liturgy to the beauty and awe of nature. You will never develop it or allow it to be developed.

If you feel that strongly, you might donate an easement to a charitable organization who can see to it that the land is never developed. It can protect and defend long after you are gone.

Question: have you made a donation?

I think you have. You kept the land, but you have donated one of your land-related legal rights – the right to develop the land.

What is this right worth?

That is the issue driving this area of tax controversy.

What if the land is on the flight path for eventual population growth and development? There was a time when Houston’s Galleria district, for example, was undeveloped land. Say you had owned the land back when. What would that easement have been worth?

You donated a potential fortune.

Let’s look at a recent case.

Plateau Holdings LLC (Plateau) owned two parcels of land in Tennessee. In fact, those parcels were the only things it owned. The land had been sold and resold, mined, and it took a while to reunite the surface and mineral rights to obtain full title to the land. It had lakes, overlooks, waterfalls and sounded postcard-worthy; it was also a whole lot out-of-the-way between Nashville and Chattanooga. Just to get utilities to the property would probably require the utility company to issue bonds to cover the cost.

Enter the investor.

He bought the two parcels (actually 98.99%, which is close enough) for approximately $5.8 million.

He worked out an arrangement with a tax-exempt organization named Foothills Land Conservancy. The easement would restrict much of the land, with the remainder available for development, commercial timber, hunting, fishing and other recreational use.

Routine stuff, methinks.

The investor donated the easement to Foothills eight days after purchasing the land.

Next is valuing the easement

Bring in the valuation specialist. Well, not actually him, as he had died before the trial started, but others who would explain his work. He had valued the easement at slightly over $25 million.

Needless to say, the IRS jumped all over this.

The case goes on for 40 pages.

The taxpayer argument was relatively straightforward. The value of the easement is equal to the reduction in the best and highest use value of the land before and after the granting of the easement.

And how do you value an undeveloped “low density mountain resort residential development”? The specialist was looking at properties in North Carolina, Georgia, and elsewhere in Tennessee. He had to assume government zoning, that financing would be available, that utilities and roads would be built, that consumer demand would exist.

There is a flight of fancy to this “best and highest” line of reasoning.

For example, I would have considered my best and highest professional “use” to be a long and successful career in the NFL. I probably would have been a strong safety, a moniker no longer used in today’s NFL (think tackling). Rather than playing on Sundays, I have instead been a tax practitioner for more than three decades.

According to this before-and-after reasoning, I should be able to deduct the difference between my earning power as a successful NFL Hall of Famer and my actual career as a tax CPA. I intend to donate that difference to the CTG Foundation for Impoverished Accountants.

Yeah, that is snark.

What do I see here?

·      Someone donated less than 100% of something.
·      That something cost about $6 million.
·      Someone waited a week and gave some of that something away.
·      That some of something was valued at more than four times the cost of the entire something. 

Nah, not buying it.

Neither did the Court.

Here is one of the biggest slams I have read in tax case in a while:

           We give no weight to the opinion of petitioner’s experts.”

The taxpayer pushed it too far.

Our case this time for the home gamers was Plateau Holdings LLC v Commissioner.

Monday, June 22, 2020

It’s A Cliff, Not A Slope


It is one of my least favorite areas of individual tax practice.

We are talking about health insurance. More specifically, health insurance purchased through the exchanges, coupled with advance payment of the premiums.

Why?

Because there is a nasty tax trap in there, and I saw the trap again the other day. It caught a client who gets by, but who is hardly in a position to service heavy tax debt.

Let’s set it up.

You can purchase health insurance in the private market or from government-sponsored marketplaces – also called exchanges. The exchanges were created under the Affordable Care Act, more colloquially known as Obamacare.

If you purchase health insurance through the exchange and your income is below a certain level, you can receive government assistance in paying the insurance premiums. Make very little income, for example, and it is possible that the insurance will be free to you. Make a little more and you will be expected to contribute to your own upkeep. Make too much and you are eliminated from the discussion altogether.

The trap has to do with the dividing line of “too much.”

Let’s look at the Abrego case.

Mr and Mrs Abrego lived in California. For 2015 he was a driver for disabled individuals, and he also prepared a few tax returns (between 20 and 30) every year. Mrs Abrego was a housekeeper.

They enrolled in the California exchange. They also did the following:

(1)  They provided an estimate of their income for 2015. Remember, the final subsidy is ultimately based on their 2015 income, which will not be known until 2016. While it is possible that someone would purchase health insurance, pay for it out-of-pocket and eventually get reimbursed by the IRS when filing their 2015 tax return in 2016, it is far more likely that someone will estimate their 2015 income to then estimate their subsidy. One would use the estimated subsidy to offset the very real monthly premiums. Makes sense, as long as all those estimated numbers come in as expected.

(2)  They picked a policy. The monthly premiums were $1,029.

(3)  The exchange cranked their expected 2015 numbers and determined that they could personally pay $108 per month.

(4)  The difference - $ 1,029 minus $108 = $921– was their monthly subsidy.

The Abregos kept this up for 10 months. Their total 2015 subsidy was $9,210 ($921 times 12).

Since the Abregos received a subsidy, they had to file a tax return. One reason is to compare actual numbers to the estimated numbers. If they guessed low on income, they would have to pay back some of the subsidy. If they guessed high, the government would owe them for underestimating the subsidy.

The Abregos filed their 2015 return.

They reported $63,332 of household income.

How much subsidy should they have received?

There is the rub.

The subsidy changes as income climbs. The subsidy gets to zero when one hits 400% of the poverty line.

What was the poverty line in California for 2015?

$15,730 for a married couple.

Four times the poverty line was $62,920.

They reported $63,332.

Which is more than $62,920.

By $412.

They have to pay back the subsidy.

How much do they have to pay back?

All of it - $9,210.

Folks, the tax rate on that last $412 is astronomical.

It is frustrating to see this fact pattern play out. The odds of a heads-up from the client while someone can still do something are – by the way – zero. That leaves retroactive tax planning, whose success rate is also pretty close to zero.

Our client left no room to maneuver. Why did her income go up? Because she sold something. Why did she not call CTG galactic command before selling – you know: just in case? What would we have done? Probably advised her to NOT SELL in the same year she is receiving a government subsidy.

How did it turn out for the Abregos?

They should have been toast, except for one thing.

Remember that he prepared tax returns. He did that on the side, meaning that he had a gig going. He was self-employed.

He got to claim business deductions.

And he had forgotten one.

How much was it?

$662.

It got their income below the magic $69,920 level.

They were on the sliding scale to pay back some of that subsidy. Some - not all.

It was a rare victory in this area.

Our case for the homegamers was Abrego v Commissioner.

Sunday, June 7, 2020

Using A Liquidating Trust


I am reading a case where the IRS wanted taxes of almost $1.5 million.

I am not surprised to read that it involved a real estate developer.

Part of tax practice is working within someone’s risk tolerance (including mine, by the way). Some clients are so risk adverse that an IRS notice – on any matter for any reason – can be interpreted as a mistake by the tax practitioner. Then you have the gunslingers at the other end of the spectrum. These are the clients you have to rope-in, for their own as well as your sake.

My experience has been that real estate developers seem to cluster around the gunslinger end of the spectrum. We have one who recently explained to me that “paying taxes means that the tax advisor made a mistake.” That, folks, is a lot of pressure … on my partner.

Jason Sage is a developer in Oregon. He represented several companies, including JLS Customs Homes. You may recall that 2008 – 2009 was a rough time for real estate, and JLS took it in the teeth. It had three projects, dragging behind approximately $18 million in debt.

Eventually the real estate market collapsed. Sage had to do something. He and his advisors decided to utilize liquidating trusts. The idea is that one transfers everything one has into a trust, which might be owned by one’s creditors; then again, it might not. The creditors might accept the settling of the trust (a fancy term for putting money and assets into a trust) as discharge of the underlying debt; then again, they might not. Each deal is its own story, and the tax consequences can vary depending on the telling.

Our story involves the transfer of three projects to three liquidating trusts. Since real estate had tanked, these transfers – treated for tax purposes as sales - threw off huge losses. These losses were so big they created overall losses - called “net operating losses” (NOLs). Tax law at the time allowed the net operating losses to travel back in time, meaning that Sage could recoup taxes previously paid.
COMMENT: I see nothing wrong with this. If the government wants to participate in one’s profits, then it can also participate in one’s losses. To do otherwise smacks more of robbery than taxation.
The IRS took a look at this arrangement and immediately called foul.

Trust taxation looks carefully at whether the trust is a separate tax entity from the person establishing the trust, funding the trust or benefiting from the trust.  There is a type called a “grantor trust” which is disregarded as a separate tax entity altogether. The most common type of grantor trust is probably the “living trust,” which has gained popularity as a probate-mitigating tool. The idea behind the grantor trust is that the grantor – say me, for example – is allowed to put money in, take money out, change beneficiaries, even terminate the trust altogether without anyone being able to gainsay my decision.

Tax law considers this to be too much control over the trust, so the trust and I are considered to be the same person for tax purposes. I would have a grantor trust. Its tax return is combined with mine.

How do I avoid this result? Well, I have to start with limiting my otherwise unrestricted control over the trust. Yield enough control and the IRS will respect the trust as separate from me.

The IRS argued that Sage’s liquidating trusts were grantor trusts. They were not separate tax entities, and one cannot sell and create a loss by selling to oneself. Without that loss, there was no NOL carryover and therefore no tax refund.

Sage had to persuade the Court that the trusts were in fact separate from him and his companies.

After all, the trusts were for the benefit of his creditors. One has to concede that creditors are an adverse party, and the existence of an adverse party is an indicator that the trust is a separate tax entity. Extrapolating, the existence of creditors means that someone with interests adverse to Sage’s own had sway over the trusts. It was that sway that made these non-grantor trusts.

Persuasive, except for one thing.

Sage had never involved the creditors when setting up the trusts.

It was hard for them to be adverse when they did not even know the trusts were there.

Our case this time was Sage v Commissioner.

Sunday, May 31, 2020

Paying Tax On Borrowed Money


I am looking at a Tax Court case where the IRS was chasing almost two-thirds of a million dollars. It involves an attorney and something called “litigation support agreements.”

There is a term you do not hear every day.

The taxpayer is a class-action lawyer.

You see, in a class action, the law firm sues on behalf of a group – or class - of affected parties. Perhaps numerous people were affected by a negligent act, for example, but there is not enough there for any one person to pursue litigation individually. Combine them, however, and you have something.

Or the lawsuit can be total malarkey and the law firm is seeking a payday, with little to no regard to the “class” it allegedly represents.

Ultimately, a class action is a tool that can be used for good or ill, and its fate depends upon the intent and will of its wielder.

Let get’s back to our taxpayer.

It takes money to pursue these cases. One has to bring in experts. There can be depositions, travel, cross-examinations. This takes money, and we already mentioned that a reason for class action is that no one person has enough reason – including money – to litigate on his/her own power.

Did you know there are people out there who will play bank with these cases? That is what “litigation support agreements” are. Yep, somebody loans money to the law firm, and – if the case hits – they get a very nice payoff on their loan. If the case fails, however, they get nothing. High risk: high reward. It’s like going to Vegas.

The taxpayer received over $1.4 million of these loans over a couple of years.

Then IRS came in.

Why?

I see two reasons, but I flat-out believe that one reason was key.

The taxpayer left the $1.4 million off his tax return as taxable income. The taxpayer thought he had a good reason for doing so: the $1.4 million represented loan monies, and it is long-standing tax doctrine that one (generally) cannot have income by borrowing money. Why? Because one has to pay it back, that is why. You are not going to get rich by borrowing money.

There are variations, though. It is also tax doctrine that one can have income when a lender forgives one’s debt. That is why banks issue Forms 1099-C (Cancellation of Debt) when they write-off someone’s credit card. How is it income? Because one is ahead by not having to pay it back.

Our taxpayer had different loan deals and agreements going, but here is representative language for one litigation support agreement:
… shall be a litigation support payment to [XXX] made on a nonrecourse basis and is used to pay for all time and expenses incurred by [XXX} in pursuant [sic] of this litigation. Said payment shall be repaid to …. at the successful conclusion of this litigation with annual interest to be paid as simple interest at the rate of …. as of the date of concluding this litigation.”
Let’s see: there is reference to repayment and an interest rate.

Good: sounds like a loan.

So where is the problem?

Let’s look at the term “nonrecourse.” In general, nonrecourse means that – if the loan fails – the lender can pursue any collateral or security under the loan. What the lender cannot do, however, is go after the borrower personally. Say I borrow a million dollars nonrecourse on a California house that subsequently declines in value to $300 grand. I can just mail the keys back to the lender and walk away without the lender able to chase me down. I am trying to divine what the broader consequence to society could possibly be if numerous people did this, but of course that is silly and could never happen.

Still, nonrecourse loans happen all the time. They should not be fatal, as I am technically still obligated on the loan - at least until the time I mail back the keys.

Let’s look at the next phrase: “successful conclusion of this litigation.”

When are you on the hook for this loan?

I would argue that you are on the hook upon “successful conclusion of this litigation.”

When are you not on the hook?

I would say any time prior to then.

The loan becomes a loan – not at the time of lending – but in the future upon occurrence of a distinguishable event.

The IRS was arguing that the taxpayer received $1.4 million for which he was not liable. He might be liable at a later time - perhaps when the universe begins to cool or the Browns win a Super Bowl – but not when that cash hit his hand.

Granted, chances are good that whoever lent $1.4 would pursue tort action if the taxpayer skipped town and sequestered on an island for a few years, but that would be a different legal action. Whoever put up the money might sue for fraud, nonperformance or malfeasance, but not because the taxpayer was liable for the debt. 

Let’s go back: what keeps one from having income when he/she borrows money?

Right: the obligation to pay it back.

So who did not have an obligation to pay it back?

The taxpayer, that’s who.

The IRS won the case. Still, what bothered me is why the IRS would go after this guy so aggressively. After all, give this arrangement a few years and it will resolve itself. The law firm receives money; the law firm spends money. When it is all said and done, the law firm will burn through all the money, leaving no “net money” for the IRS to tax.

So what fired up the IRS?

The taxpayer filed for bankruptcy.

Before burning through the money.

Meaning there was “net money” left.

He was depriving the IRS of its cut.

There is the overwhelming reason I see.

Our case this time was Novoselsky v Commisioner.