There Is No Tax Relief If You Are Robbed

 

Some tax items have been around for so long that perhaps it would be best to leave them alone.

I’ll give you an example: employees deducting business mileage on their car.

Seems sensible. You tax someone on their work income. That someone incurs expenses to perform that work. Fairness and equity tell you that one should be able to offset the expenses of generating the income against such income.

The Tax Cut and Jobs Act of 2017 (TCJA) did away with that deduction, however. Mind you, the TCJA itself expires in 2025, so we may see this deduction return for 2026.

There are reasons why Congress eliminated the deduction, we are told. They increased the standard deduction, for example, and one could not claim the mileage anyway if one’s itemized deductions were less than the standard deduction. True statement.

Still, it seems to me that Congress could have left the deduction intact. Many if not most would not use it (because of the larger standard deduction), but the high-mileage warriors would still have the deduction if they needed it.

Here’s another:  a tree falls on your house. Or you get robbed.

This has been a tax break since Carter had liver pills.

Used to be.

Back to the TCJA. Personal casualty and theft losses are deductible only if the loss results from a federally declared disaster.

Reread what I just said.

What does theft have to do with a federally declared disaster?

Nothing, of course.

I would make more sense to simply say that the TCJA did away with theft loss deductions.

Let’s talk about the Gomas case.

Dennis and Suzanne Gomas were retired and living their best life in Florida. Mr. G’s brother died, and in 2010 he inherited a business called Feline’s Pride. The business sold pet food online.

OK.

The business was in New York.

We are now talking about remote management. There are any numbers of ways this can go south.

His business manager in New York must have binged The Sopranos, as she was stealing inventory, selling customer lists, not supervising employees, and on and on.

Mr. G moved the business to Florida. His stepdaughter (Anderson) started helping him.

Good, it seems.

By 2015 Mr. G was thinking about closing the business but Anderson persuaded him to keep it open. He turned operations over to Anderson, although the next year (2016) he formally dissolved the company. Anderson kept whatever remained of the business.

In 2017 Anderson prevailed on the G’s to give her $20,000 to (supposedly) better run the business.

I get it. I too am a parent.

Anderson next told the Gs that their crooked New York business manager and others had opened merchant sub-accounts using Mr. G’s personal information. These reprobates were defrauding customers, and the bank wanted to hold the merchant account holder (read: Mr. G) responsible.

          COMMENT: Nope. Sounds wrong. Time to lawyer up.

Anderson convinced the G’s that she had found an attorney (Rickman), and he needed $125,000 at once to prevent Mr. G’s arrest.

COMMENT: For $125 grand, I am meeting with Rickman.

The G’s gave Anderson the $125,000.

But the story kept on.

There were more business subaccounts. Troubles and tribulations were afoot and abounding. It was all Rickman could do to keep Mr. G out of prison. Fortunately, the G’s had Anderson to help sail these treacherous and deadly shoals.

The G’s never met Rickman. They were tapping all their assets, however, including retirement accounts. They were going broke.

Anderson was going after that Academy award. She managed to drag in friends of the family for another $200 grand or so. That proved to be her downfall, as the friends were not as inclined as her parents to believe. In fact, they came to disbelieve. She had pushed too far.

The friends reached out to Rickman. Sure enough, there was an attorney named Rickman, but he did not know and was not representing the G’s. He had no idea about the made-up e-mail address or merchant bank or legal documents or other hot air.

Anderson was convicted to 25 years in prison.

Good.

The G’s tried to salvage some tax relief out of this. For example, in 2017 they had withdrawn almost $1.2 million from their retirement accounts, paying about $410 grand in tax.

Idea: let’s file an amended return and get that $410 grand back.

Next: we need a tax Code-related reason. How about this: we send Anderson a 1099 for $1.1 million, saying that the monies were sent to her for expenses supposedly belonging to a prior business.

I get it. Try to show a business hook. There is a gigantic problem as the business had been closed, but you have to swing the bat you are given.

The IRS of course bounced the amended return.

Off to Court they went.

You might be asking: why didn’t the G’s just say what really happened – that they were robbed?

Because the TCJA had done away with the personal theft deduction. Unless it was presidentially-declared, I suppose.

So, the G’s were left bobbing in the water with much weaker and ultimately non-persuasive arguments to power their amended return and its refund claim.

Even the judge was aghast:

Plaintiffs were the undisputed victims of a complicated theft spanning around two years, resulting in the loss of nearly $2 million dollars. The thief — Mrs. Gomas’s own daughter and Mr. Gomas’s stepdaughter — was rightly convicted and is serving a lengthy prison sentence. The fact that these elderly Plaintiffs are now required to pay tax on monies that were stolen from them seems unjust.

Here is Court shade at the IRS:

In view of the egregious and undisputed facts presented here, it is unfortunate that the IRS is unwilling — or believes it lacks the authority — to exercise its discretion and excuse payment of taxes on the stolen funds.

There is even some shade for Congress:

It is highly unlikely that Congress, when it eliminated the theft loss deduction beginning in 2018, envisioned injustices like the case before this Court. Be that as it may, the law is clear here and it favors the IRS. Seeking to avoid an unjust outcome, Plaintiffs have attempted to recharacterize the facts from what they really are — a theft loss — to something else. Established law does not support this effort. The Court is bound to follow the law, even where, as here, the outcome seems unjust.

To be fair, Congress changed the law. The change was unfair to the G’s, but the Court could not substitute penumbral law over actual law.

The G’s were hosed.

Seriously, Congress should have left theft losses alone. The reason is the same as for employee mileage. The Code as revised for TCJA would make most of the provision superfluous, but at least the provision would exist for the most extreme or egregious situations.

COMMENT: I for one am hopeful that the IRS and G's will resolve this matter administratively. This is not a complementary tale for the IRS, and – frankly – they have other potentially disastrous issues at the moment. It is not too late, for example, for the IRS and G’s to work out an offer in compromise, a partial pay or a do-not-collect status. This would allow the IRS to resolve the matter quietly. Truthfully, they should have already done this and avoided the possible shockwaves from this case.

Our case this time was Gomas v United States, District Court for the Middle District of Florida, Case 8:22-CV-01271.

Tax Preparer Gives Gambler A Losing Hand

 

I am looking at a bench opinion.

The tax issue is relatively straightforward, so the case is about substantiation. To say that it went off the rails is an understatement.

Let us introduce Jacob Bright. Jacob is in his mid-thirties, works in storm restoration and spends way too much time and money gambling. The court notes that he “recognizes and regrets the negative effect that gambling has had on his life.”

He has three casinos he likes to visit: two are in Minnesota and one in Iowa. He does most of his sports betting in Iowa and plays slots and table games in Minnesota.

He reliably uses a player’s card, so the casinos do much of the accounting for him.

Got it. When he provides his paperwork to his tax preparer, I expect two things:

(1)  Forms W-2G for his winnings

(2)  His player’s card annual accountings

The tax preparer adds up the W-2Gs and shows the sum as gross gambling receipts. Then he/she will cross-check that gambling losses exceed winnings, enter losses as a miscellaneous itemized deduction and move on. It is so rare to see net winnings (at least meaningful winnings) that we won’t even talk about it.

COMMENT: Whereas the tax law changed in 2018 to do away with most miscellaneous itemized deductions, gambling losses survived. One will have to itemize, of course, to claim gambling losses.   

Here starts the downward cascade:

Mr. Bright hired a return preparer who was recommended to him, but he did not get what or whom he expected. Rather than the recommended preparer, the return preparer’s daughter actually prepared his return.”

OK. How did this go south, though?

The return preparer reported that Mr. Bright was a professional gambler ….”

Nope. Mind you, there are a few who will qualify as professionals, but we are talking the unicorns. Being a professional means that you can deduct losses in excess of winnings, thereby possibly creating a net operating loss (NOL). An NOL can offset other income (up to a point), income such as one’s W-2. The IRS is very, very reluctant to allow someone to claim professional gambler status, and the case history is decades long. Jacob’s preparer should have known this. It is not a professional secret.

Jacob did not review the return before signing. For some reason the preparer showed over $240 grand of gross gambling receipts. I added up the information available in the opinion and arrived at little more than $110 grand. I have no idea what she did, and Jacob did not even realize what she did. Perhaps she did not worry about it as she intended the math to zero-out.

She should not have done this.

The IRS adjusted the initial tax filing to disallow professional gambler status.

No surprise.

Jacob then filed an amended return to show his gambling losses as miscellaneous itemized deductions. He did not, however, correct his gross gambling winnings to the $110 grand.

The IRS did not allow the gambling losses on the amended return.

Off to Tax Court they went.

There are several things happening:

(1)  The IRS was arguing that Jacob did not have adequate documentation for his losses. Mind you, there is some truth to this. Casino reports showed gambling activity for months with no W-2Gs (I would presume that he had no winnings, but that is a presumption and not a fact). Slot winnings below $1,200 do not have to be reported, and he gambled on games other than slots. Still, the casino reports do provide some documentation. I would argue that they provide substantiation of his minimum losses.

(2)  Let’s say that the IRS behaved civilly and allowed all the losses on the casino reports. That is swell, but the tax return showed gambling receipts of $240 grand. Unless the casino reports showed losses of (at least) $240 grand, Jacob still had issues.

(3)  The Court disagreed with the IRS disallowing all gambling deductions. It looked at the casino reports, noting that each was prepared differently. Still, it did not require advanced degrees in mathematics to calculate the losses embedded in each report. The Court calculated total losses of slightly over $191 grand. That relieved a lot – but not all – of the pressure on Jacob.

(4)  Jacob did the obvious: he told the Court that the $240 grand of receipts was a bogus number. He did not even know where it came from.

(5)  The IRS immediately responded that it was being whipsawed. Jacob reported the $240 grand number, not the IRS. Now he wanted to change it. Fine, said the IRS: prove the new number. And don’t come back with just numbers reported on W-2Gs. What about smaller winnings? What about winnings from sports betting? If he wanted to change the number, he was also responsible for proving it.

The IRS had a point. It was being unfair and unreasonable but also technically correct.

Bottom line: the IRS was not going to permit Jacob to reduce his gross receipts number without some documentation. Since all he had was the casino reports, the result was that Jacob could not change the number.

Where does this leave us? I see $240 – $191 = $49 grand of bogus income.

My takeaway is that we have just discussed a case of tax malpractice. That is what lawyers are for, Jacob.

Our case this time was Jacob Bright v Commissioner, Docket No. 0794-22.

Losing A Casualty Loss

 

I have stayed away from talking about casualty losses.

To be fair, one needs to distinguish business casualty losses from personal casualty losses. Business casualties are still deductible under the Code. Personal casualties are not. This change occurred with the Tax Cut and Jobs Act of 2017 and is tax law until 2025, when much of it expires.

This is the tax law that did away with office-in-home deductions, for example. Great timing given that COVID would soon have multitudes working from home.

It also did away with personal casualty losses, with an exception for presidentially - declared disaster areas.

Have someone steal your personal laptop. No casualty loss. Accident with your personal car? No casualty loss. Lost your house during the storms and tornados in western Tennessee at the end of March 2023? That would be a casualty loss because there was a presidential declaration.

I consider it terrible tax law, but Congress was primarily concerned about finding money.  

I am reading a case that involves casualty losses. Two, in fact. The Court included several humorous flourishes in its decision.

Let’s go over it.

Thomas Richey and his wife Maureen Cleary bought a second home in Stone Harbor on Cape May in the south of New Jersey. The house was on the waterfront with access to the open ocean. They also bought a 40-foot boat.

Sounds nice.

In 2017 storm Stella hit.

Richey and Cleary claimed casualty losses totaling over $820,000 on their 2017 tax return.

That will catch attention.

Here is the Court:

Such a large loss - one that caused them to reduce their adjusted gross income of more than $850,000 to a taxable income of zero – bobbed into the Commissioner’s view, and he selected their return for audit.”

The Commissioner did more than select the return; he denied the casualty loss deduction altogether.

Richey and Cleary petitioned the Tax Court.

Yep. Had to.

Whereas they lived in Maryland (remember: New Jersey was their second home), they petitioned the Court for trial in Los Angeles.

I do not get the why. Very little upside. Possible massive downside.

We added the case to one of our trial calendars for Los Angeles, but on the first day of that session neither petitioner showed up.”

Uh, Richey …?!

We postponed trial for a day to enable Richey to testify via Zoom.”

Richey explained that he learned about the trial only a week before, and even then, no one gave him specific details.

We do not find this credible ….”

This could have started better. 

The couple’s case began taking on water right at the start…”

The Court seemed amused.

Back to business, Richey. Let’s first establish that a casualty occurred.

He testified that he had taken pictures of the damage to both boat and home on his phone shortly after the storm.”

Good.

He explained, however, that a later software update to his phone deleted them.”

Seriously?

That left him to introduce only photographs of the house taken … nearly a year after the storm hit and after reconstruction had already begun.”

A year? Were you that busy?

These photographs depict no visible damage other than that which one might see at any construction site, and we could see nothing that showed damage that we could specifically attribute to the storm. “

Richey, I have a question for you.

… we did not find Richey’s testimony, standing alone, credible on this point.”

Have you seen John Wick?

As for the boat, the couple introduces a photograph of what the boat looked like before the storm, but nothing to show what it looked like afterwards. The couple also gave us no receipts for any boat repairs.”

Tell me the truth: did you do something to this judge’s dog?

Whom are we to believe?”

Richey, this is legal-speak for “we do not believe you.”

OK, we are going to have to lean double hard on the appraisals. Those involve third parties, so maybe we can get the Court to back off a bit.

Richey and Cleary did not get an appraisal of their own home valuing it before and after the storm.”

And may I ask why, Richey?

Richey instead consulted a real-estate agent who provided them with Multiple Listing Service (MLS) printouts of other people’s homes. This is a problem for many different reasons.”

You think?

The first … is that he didn’t talk to this agent until after the audit had begun.”

I have an idea, Richey, but it’s a long shot.

It is not impossible for a homeowner to conduct an appraisal himself …”

Richey, go improv. You live in Cape May. You know the prices. You know the damage the storm wrought. Make the Court believe you. Sell it.

They also produced no evidence of their awareness of market conditions in Stone Harbor. What we got were photographs of MLS printouts.”

You are a man of commitment and sheer will, Richey.

We infer from Richey’s having to reach out to an agent to give him such comparables an unspoken admission that he is not qualified to conduct an adequate appraisal on his own.”

I am familiar with the parlance, Richey.

If the absence of proof of damage causes the couple’s case to founder, the absence of proof on valuing that damage causes it to sink altogether.”

Well, that’s that. Maybe we can get something on the boat.

Richey and Cleary fare no better on the loss they claim for their boat.”

Richey, walk out of here with your pride intact.

All these attacks by the Commissioner have picked completely clean the flesh of their claimed deduction.”

Richey, just walk out of here.

Richey’s first mistake was scheduling a Tax Court hearing in Los Angeles. That led to the disastrous failure-to-show, which clearly angered the Court. The Court felt they were being lied to, and they never relented. The lack of an appraisal – while not necessarily having to be fatal – was fatal in this case. Richey was unable to persuade the Court that he had the experience or expertise to substitute for an appraisal.    

Sometimes the Court will carry water for a petitioner who is underprepared. We have reviewed a couple of these cases before, but that beneficent result presupposes the Court likes the person. That was not a factor here.

Our case this time was Richey and Cleary v Commissioner, T.C. Memo 2023-43.

Donating Cryptocurrency

 

I was reading something recently, and it reminded me how muddled our tax Code is.

Let’s talk about cryptocurrency. I know that there is bad odor to this topic after Sam Bankman-Fried and FTX, but cryptocurrencies and their exchanges are likely a permanent fixture in the financial landscape.

I admit that I think of cryptos – at least the main ones such as Bitcoin, Ethereum or Binance Coin – as akin to publicly traded stock. You go to www.finance.yahoo.com , enter the ticker symbol and see Bitcoin’s trading price. If you want to buy Bitcoin, you will need around $23 grand as I write this.

Sounds a lot like buying stock to me.   

The IRS reinforced that perspective in 2014 when it explained that virtual currency is to be treated as property for federal income tax purposes. The key here is that crypto is NOT considered a currency. If you buy something at Lululemon, you do not have gain or loss from the transaction. Both parties are transacting in American dollars, and there is no gain or loss from exchanging the same currency.

COMMENT: Mind you, this is different from a business transaction involving different currencies. Say that my business buys from a Norwegian supplier, and the terms require payment in krone within 20 days. Next say that the dollar appreciates against the krone (meaning that it takes fewer dollars to purchase the same amount of krone). I bought something costing XX dollars. Had I paid for it then and there, the conversation is done. But I did not. I am paying 20 days later, and I pay XX minus Y dollars. That “Y” is a currency gain, and it is taxable.

So, what happens if crypto is considered property rather than currency?

It would be like selling Proctor and Gamble stock (or a piece of P&G stock) when I pay my Norwegian supplier. I would have gain or loss. The tax Code is not concerned with the use of cash from the sale.

Let’s substitute Bitcoin for P&G. You have a Bitcoin-denominated wallet. On your way to work you pick-up and pay for dry cleaning, a cup of coffee and donuts for the office. What have you done? You just racked up more taxable trades before 9 a.m. than most people will all day, that is what you have done.

Got it. We can analogize using crypto to trading stock.

Let’s set up a tax trap involving crypto.

I donate Bitcoin.

The tax Code requires a qualified appraisal when donating property worth over $5,000.

I go to www.marketwatch.com.

I enter BTC-USD.

I see that it closed at $22,987 on January 27, 2023. I print out the screen shot and attach it to my tax return as substantiation for my donation.

Where is the trap?

The IRS has previously said crypto is property, not cash.

A donation of property worth over $5 grand generally requires an appraisal. Not all property, though. Publicly-traded securities do not require an appraisal.

So is Bitcoin a publicly-traded security?

Let’s see. It trades. There is an organized market. We can look up daily prices and volumes.

Sounds publicly-traded.

Let’s look at Section 165(g)(2), however:

    (2)  Security defined.

For purposes of this subsection, the term "security" means-

(A)  a share of stock in a corporation;

(B)  a right to subscribe for, or to receive, a share of stock in a corporation; or

(C)  a bond, debenture, note, or certificate, or other evidence of indebtedness, issued by a corporation or by a government or political subdivision thereof, with interest coupons or in registered form.

The IRS Office of Chief Counsel looked at this and concluded that it could not see crypto fitting the above categories.

Crypto could therefore not be considered a security.

As property not a security, any donation over $5 grand would require a qualified appraisal.

There was no qualified appraisal in our example. All I did was take a screen shot and include it with the return.

That means no charitable deduction.

I have not done a historical dive on Section 165(g)(2), but I know top-of-mind that it has been in the Code since at least 1986.

Do you know what did not exist in 1986?

The obvious.

Time to update the law, me thinks.

This time we were discussing CCA 202302012.

A Good Hire Can Help Prove You Are Serious About A Business

If you have gig, there is a presumption in the Code that it will be profitable.

Mind you, it may not be profitable every year. Not even Fortune 100 companies are profitable every year.  Still, the gig is expected to be profitable on a cumulative basis.

Seems obvious. Why are we talking about this?

Say that you have an internet-based business. The business itself is profitable, but you are spending so much on research, hardware, and infrastructure that - overall – the business shows a loss. You know better. You know that, soon enough, the business will turn the corner, those expenses will taper off, and you will make a fortune.

Or maybe you are funding a promising teenage boxer. Everyone sees the potential for the next Mike Tyson. You see it too.

What if your business is sitting on land that will one day be – if it is not already – absurdly valuable? Even if the business is unprofitable, the sale of the land will eventually trump those losses.

We are talking about hobby losses. You say it is a business. The IRS says it is not. It is one of the trickiest areas in the Code.  

There are several repetitive factors that the IRS looks for, such as:

(1)  You don’t treat it like a business. Little things are a tell, like not having accounting and not pivoting when it seems clear you have a loser.

(2)  You make a ton of money elsewhere, so it is financially insignificant whether that activity ever shows a profit.

(3)  You derive a high degree of personal pleasure from the activity.

Let’s look at a recent hobby loss case.

In 2004 the Wondries bought an 1,100-acre ranch in California. They borrowed at the bank, indicating in the paperwork that they would make money by selling cattle and providing guided hunting expeditions.

Mr. Wondries was a sharp cookie. He had already owned around 23 car dealerships, and he had a track record of turning losing dealerships into profitable ones.

He had no experience in ranching, though, so he hired someone (Mr. Palm) who did. Wondries hired Palm the same day he bought the ranch.

Good thing. Palm was mentoring Wondries on the fly, and they both realized that cattle raising was a no-go. They could not overcome feed prices. They thought about allowing the cattle to graze in the fields and growing their own barley, but a drought soon took away that option.

There was no money there. They sold most of the cattle.

Pivot.

Next was the guided hunting expeditions. The ranch was too small for certain (read: the desirable and profitable) hunts. We haven’t even mentioned insuring a hunting activity.

Bye to hunting.

Pivot again.

Wondries and Palm still thought they could make money by holding the land for investment. Seems that Wondries bought the land at a good price, so there was room to run.

Over three years (2016 to 2017) the ranch lost over $925 grand. You and I would have run for the hills, but Mr. Wondries’ W-2’s for the period totaled over $12 million. He could take a financial hit.

Big W-2. Substantial losses from a gig. Looks like meaningful personal pleasure is involved. The IRS caught scent and went for it.  Hobby loss. No loss deductions for you.

Off to Tax Court they went.

These cases tend to be very fact specific. While there are criteria the courts repetitively consider, that does not mean each court interprets, applies, or weights the criteria in the same manner.

Let’s go over them briefly.

(1)  The way taxpayer conducts the activity

 

The Court saw a business plan, an accounting system, and the hiring of an industry pro.

 

This went in the taxpayers’ favor.

 

(2)  Expertise of taxpayer or advisors

 

Wondries’ expertise was in dealerships, but he recognized that and hired a ranching pro. He also listened to the pro while trying to make the ranch profitable.

 

This went in the taxpayers’ favor.

 

(3)  Time and effort expended by taxpayer

 

The Wondries together spent an average of six days per month at the ranch. It was not much in the scheme of things.

 

To be fair, they had other stuff going on.

 

This still went in the taxpayers’ favor. Why? Because the manager was there full-time, and his time was imputed to the Wondries.

 

(4)  Expectation that assets used in activity will appreciate   

 This went in the taxpayers’ favor.

 

(5)  Taxpayer success in other activities

 

Wondries was a successful businessman.  

 

This went in the taxpayers’ favor.

 

(6)  History of activity income or loss

 

The ranch was a loser.

 

This went against the taxpayers.

 

(7)  The amount of profits compared to losses

 

The concept here is whether there were wee profits against huge losses.

 

This went against the taxpayers.

 

(8)  Taxpayer financial status

 

The Wondries were loaded.

 

This went against the taxpayers.

 

(9)  Elements of personal pleasure in the activity

 

The IRS pounced on this one. A ranch? Does anything say personal pleasure like a ranch?

 

The Court thought otherwise. They noted that the Wondries were working when they were there. They were hiking, biking, or boating when they visited their other properties. This lowers one’s motivation in wanting to visit the ranch.

 

The Court spotted the taxpayers this one.

 

The Tax Court decided the ranching activity was a business and not a hobby.

Not surprisingly, they also noted that:

                  This is a close case.”

What swung it for the Wondries?

Two things stand out to me:

(1)  The Court did not see significant personal pleasure in owning the ranch. In fact, it sounded like any pleasure from showing- off the ranch was more than offset by working every time the Wondries visited.

(2)  Hiring an industry pro to run the place. By my count, the ranch manager swung the Court’s decision in at least three of the above criteria

Hobby loss cases are fickle. What can tax advisors take away from this case?

Hire a pro to run the thing. Give the pro authority. Listen to the pro. Pivot upon that advice.

To say it differently, don’t be this:

Our case this time was Wondries v Commissioner, T.C. Memo 2023-5.

Keeping Records For More Than Three Years

 

How long should you keep tax records?

We have heard that one should keep records for at least three years, as the IRS has three years to examine your return.

There is a lot of wiggle room there, however.

Let’s look at a wiggle that repeats with some frequency: a net operating loss (NOL) carryover.

An NOL occurs when a business’ tax deductions exceed its tax revenues.

I include the word “business” intentionally. Nonbusiness income - think interest, dividends, royalties – will not generate NOLs, unless you happen to own a bank or something. That would be rare, but it could happen.

An NOL is a negative (net) number from a business.

How does this negative number get on your personal return?

Several ways. Here is one: you own a piece of a passthrough business and receive a Schedule K-1.  

A passthrough normally does not pay taxes on its own power. Its owners do. If that passthrough had a big enough loss, your share of its loss might wipe out all the other income on your personal return. It happens. I have seen it.

You would go negative. Bingo, you have an NOL.

But what do you do with it?

The tax law has varied all over the place on what to do with it. Sometimes you could take it back five years. Sometimes two. Sometimes you could not take it back at all. What you could not take back you could take forward to future years. How many future years? That too has varied. Sometimes it has been fifteen years. Sometimes twenty. Right now, it is to infinity and beyond.

Let’s introduce Betty Amos.

Betty was a Miami CPA and restaurateur.  In the early 1980s she teamed up with two retired NFL players to own and operate Fuddruckers restaurants in Florida.

She wound up running 15 restaurants over the next 27 years.

She was honored in 1993 by the National Association of Women Business Owners. She was named to the University of Miami board of trustees, where she served as chair of the audit and compliance committee.

I am seeing some professional chops.

In 1999 her share of Fudddruckers generated a taxable loss. She filed a joint tax return with her husband showing an NOL of approximately $1.5 million.

In 2000 she went negative again. Her combined NOL over the two years was pushing $1.9 million.

Let’s fast forward a bit.

On her 2014 tax return she showed an NOL carryforward of $4.2 million.

We have gone from $1.9 to $4.2 million. Something is sinking somewhere.

On her 2015 tax return she showed an NOL carryforward of $4.1 million.

That tells me there was a positive $100 grand in 2014, as the NOL carryforward went down by a hundred grand.

Sure enough, the IRS audited her 2014 and 2015 tax years.

More specifically, the IRS was looking at the big negative number on those returns.

Prove it, said the IRS.

Think about this for a moment. This thing started in 1999. We are now talking 2014 and 2015. We are well outside that three-year period, and the IRS wants us to prove … what, specifically?

Just showing the IRS a copy of your 1999 return will probably be insufficient. Yes, that would show you claiming the loss, but it would not prove that you were entitled to the loss. If a K-1 triggered the loss, then substantiation might be simple: just give the IRS a copy of the K-1. If the loss was elsewhere – maybe gig work reported on Schedule C, for example - then substantiation might be more challenging. Hopefully you kept a bankers box containing bank statements, invoices, and other records for that gig activity.

But this happened 15 years ago. Should you hold onto records for 15 years?

Yep, in this case that is the wise thing to do.

Let me bring up one more thing. In truth, I think it is the thing that got Betty in hot water.

When you have an NOL, you are supposed to attach a schedule to your tax return every year that NOL is alive. The schedule shows the year the NOL occurred, its starting amount, how much has been absorbed during intervening years, and its remaining amount. The IRS likes to see this schedule. Granted, one could fudge the numbers and lie, but the fact that a schedule exists gives hope that one is correctly accounting for the NOL.

Betty did not do this.

Betty knew better.

Betty was a CPA. 

The IRS holds tax professionals to a higher standard.

BTW, are you wondering how the IRS reconciles its Indiana-Jones-like stance on Betty’s NOL with a three-year-statute-of-limitations?

Easy. The IRS cannot reach back to 1999 or 2020; that is agreed.

Back it can reach 2014 and 2015.

The IRS will not permit an NOL deduction for 2014 or 2015. Same effect as reaching back to 1999 or 2000, but it gets around the pesky statute-of-limitations issue.

And in the spirit of bayoneting-the-dead, the IRS also wanted penalties.

Betty put up an immediate defense: she had reasonable cause. She had incurred those losses before Carter had liver pills. Things are lost to time. She was certain that she carried numbers correctly forward from year to year.

Remember what I said about tax professionals? Here is the Court:

More significantly, Ms. Amos is a longtime CPA who has worked for high-profile clients, owned her own accounting firm, and been involved with national and state CPA associations. It beggars belief that she would be unaware that each tax years stands alone and that it was her responsibility to demonstrate her entitlement to the deductions she claimed.”

Yep, she was liable for penalties too.

Our case this time was Betty Amos v Commissioner, T.C. Memo 2022-109.