An Estate And An IRA Rollover

 

Retirement accounts can create headaches with the income taxation of an estate.

We know that – if one is wealthy enough – there can be an estate tax upon death. I doubt that is a risk for most of us. The new tax bill (the One Big Beautiful …), for example, increases the lifetime estate tax exclusion to $15 million, with future increases for inflation. Double that $15 million if you are married. Yeah, even with today’s prices $30 million is pretty strong.

What we are talking about is not estate tax, however, but income tax on an estate.

How can an estate have income tax, you wonder? The concept snaps into place if you think of an estate with will-take-a-while-to-dispose assets. Let’s say that someone passes away owning the following:

·       Checking and savings accounts

·       Brokerage accounts

·       IRAs and 401(k)s

·       Real estate

·       Collectibles

The checking and savings accounts are easy to transfer to the estate beneficiaries. The brokerage accounts are a little more work - you would want to obtain date-of-death values, for example – but not much more than the bank accounts. The IRAs and 401(k)s can be easy or hard, depending on whether the decedent left a designated beneficiary. Real estate can also be easy or hard. If we are selling a principal residence, then – barring deferred maintenance or unique circumstances – it should be no more difficult than selling any other house. Change this to commercial property and you may have a different answer. For example, a presently unoccupied but dedicated structure (think a restaurant) in a smaller town might take a while to sell. And who knows about collectibles; it depends on the collectible, I suppose.

Transferring assets to beneficiaries or selling assets and transferring the cash can take time, sometimes years. The estate will have income or loss while this is happening, meaning it will file its own income tax return. In general, you do not want an estate to show taxable income (or much of it). A single individual, for example, hits the maximum tax bracket (37%) at approximately $626,000 of taxable income. An estate hits the 37% bracket at slightly less than $16 grand of taxable income. Much of planning in this area is moving income out of the estate to the beneficiaries, where hopefully it will face a lower tax rate.

IRAs and 401(k)s have a habit of blowing up the planning.

In my opinion, IRAs and 401(k)s should not even go to an estate. You probably remember designating a beneficiary when you enrolled in your 401(k) or opened an IRA. If married, your first (that is, primary) beneficiary was probably your spouse. You likely named your kids as secondary beneficiaries. Upon your death, the IRA or 401(k) will pass to the beneficiary(ies) under contract law. It happens automatically and does not need the approval – or oversight – of a probate judge.

So how does an IRA or 401(k) get into your estate for income taxation?

Easy: you never named a beneficiary.

It still surprises me – after all these years - how often this happens.

So now you have a chunk of money dropping into a taxable entity with sky-high tax rates.

And getting it out of the estate can also present issues.

Let’s look at the Ozimkoski case.

Suzanne and Thomas Ozimkoski were married. He died in 2006, leaving a simple two-page will and testament instructing that all his property (with minimal exceptions) was to go to his wife. Somewhere in there he had an IRA with Wachovia.

During probate, his son (Ozimkoski Junior) filed two petitions with the court. One was for outright revocation of his father’s will.

Upon learning of this, Wachovia immediately froze the IRA account.

Eventually Suzanne and Junior came to an agreement: she would pay him $110 grand (and a 1967 Harley), and he would go away. Junior withdrew both petitions before the probate court.

Wachovia of course needed copies: of the settlement, of probate court approval, and so on). There was one more teeny tiny thing:

… Jr had called and told a different Wachovia representative that he did not want an inherited IRA.”

What does this mean?

Easy. Unless that IRA was a Roth, somebody was going to pay tax when money came out of the account. That is the way regular IRAs work: it is not taxable now but is taxable later when someone withdraws the money.

My first thought would be to split the IRA into two accounts: one remaining with the estate and the second going to Junior.

Junior however understood that he would be taxed when he took out $110 grand. Junior did not want to pay tax: that is what “he did not want an inherited IRA” means.

It appears that Suzanne was not well-advised. She did the following: 

·       Wachovia transferred $235 grand from the estate IRA to her IRA.

·       Her IRA then distributed $141 grand to her.

·       She in turn transferred $110 grand to Junior.

Wachovia issued Form 1099-R to Suzanne for the distribution. There was no 1099-R to Junior, of course. Suzanne did not report the 1099-R because some of it went (albeit indirectly) to Junior. The IRS computers hummed and whirred, she received notices about underreporting income, and we eventually find her in Tax Court.

She argued that the $110 grand was not her money. It was Junior’s, pursuant to the settlement.

The IRS said: show me where Junior is a beneficiary of the IRA.

You don’t understand, Suzanne argued. There is something called a “conduit” IRA. That is what this was. I was the conduit to get the money to Junior.

The IRS responded: a conduit involves a trust, with Junior as the ultimate beneficiary of the trust. Is there a trust or trust agreement we can look at?

There was not, of course.

Junior received $110 grand, and the money came from the IRA, but Junior was no more a beneficiary of that IRA than you or I.

Back to general tax principles: who is taxed on an IRA distribution?

The person who receives the distribution – that is, the IRA beneficiary.

What if that person immediately transfers the distribution monies to someone else?

Barring unique circumstances – like a conduit – the transfer changes nothing. If Suzanne gave the money to her church, she would have a charitable donation. If she gave it to her kids, she might have a reportable gift. If she bought a Mercedes, then she bought an expensive personal asset. None of those scenarios keeps her from being taxed on the distribution.

Here is the Court:

What is clear from the record before the Court is that petitioner’s probate attorney failed to counsel here on the full tax ramifications of paying Mr. Ozimkoski, Jr., $110,000 from her own IRA.”

While the Court is sympathetic to petitioner’s argument, the distributions she received were from her own IRA and therefore are considered taxable income to her …”

She was liable for the taxes and inevitable penalties the IRS piled on.

Was this situation salvageable?

Not if Junior wanted $110,000 grand with no tax.

It was inevitable that someone was going to pay tax.

If Junior did not want tax, the $110 grand should be reduced by taxes that either Suzanne or the estate would pay on his behalf.

If Junior refused, then the settlement was not for $110 grand; it instead was for $110 grand plus taxes. That arrangement might have been acceptable to Suzanne, but – considering that she went to Tax Court – I don’t think it was.

The Court noted that Suzanne was laboring.

… she was overwhelmed by circumstances surrounding the will contest.”

While the Court is sympathetic to petitioner’s situation …”

Let me check on something. Yep, this is a pro se case.

Suzanne was relying on her probate attorney for tax advice. It seems clear that her attorney did not spot the issue. I would say Suzanne’s reliance on her attorney was misplaced.

Our case this time was Suzanne D. Oster Ozimkoski v Commissioner, T.C. Memo 2016-228.

The Change-Of-Address Rules Matter

 

The IRS requests that one alert them of change-of-address when one moves. There is even a form, but I do not often see the form used in practice. Normally the IRS is alerted when one files the next tax return with the new address.

It is, by the way, a good idea to alert the IRS of a change of address in case you have the misfortune of tax notices. There is a clock for certain tax notices, and once they start it can be difficult to reverse the clock.

I will give you one, as it has become more repetitive in practice than I would have liked: the notice of deficiency, also called a “statutory” notice of deficiency. I generally refer to it as the SNOD.

We have talked about the SNOD before. The IRS wants to reduce its tax assessment to a judgement. That requires the intervention of a court - the Tax Court in this case - and the IRS sends out a multipage, impressive, imposing if not intimidating notice to the taxpayer.

Who in turn collects it with other tax documents - unread - and drops the bundle off a-half-year later (or more) when it is time to meet with the CPA.

There is a problem here: one has 90 days to respond to a SNOD.

Which has passed. The level of difficulty has increased. The matter has already defaulted in favor of the IRS, of course, as the taxpayer never responded. The IRS has unleashed its Collections berserkers, who have little interest whether you actually owe the tax or not.

Here is a Collections story from several years ago. The IRS proposed changes to a client’s tax return. Sure enough, the SNOD got lost in the mail, was stolen from the mailbox, was thrown in the trash, whatever. The IRS changed numbers here and there. Some numbers were small and of minor import. Others were 1099s issued to our client but belonging elsewhere among related taxpayers. Then there was the big number: the rollover of a 401(k) or IRA. A 1099 is issued for a rollover, although it is normally a nontaxable event. The 1099 has a unique code for a rollover. The IRS, the taxpayer and accountant see the code, and everybody moves on.

Not this time.

The IRS did not see the code. Underreported income! Fair share! Tax the rich! The IRS went through its dunning notice series, eventually its SNOD, and then Collections activity. They filed a lien. They were irate, as they thought the taxpayer was ignoring them.

The taxpayer had no idea. It was only when trying to sell some real estate that the lien – and the rest of the story - came to light.

We went all Sherlock on what had happened.

We filed an amended return to reverse the IRS adjustment. We had Collections hold back the war dogs to allow the IRS time to process the amended return.

Which never happened. Collections came back more frenzied than before.

The system had failed. We wanted to know where that amended return was. The IRS is not built for self-reflection, BTW, but we eventually found the return. Someone in Kansas City had started to work the file, I presume quitting time arrived and – as an example of why people hate government unions – never got back to our client. Never. As in ever.

Yeah, the matter eventually got resolved, but it had become a sinkhole of professional time. I did talk with a very pleasant IRS attorney from Nashville, who - once the matter got to her - moved heaven and earth to reverse the lien.

And there you have an example of how not responding to a SNOD can sour someone’s life.

And an example of why I believe that the IRS should be required to reimburse a tax professional’s time when the IRS fails to follow procedures or otherwise just do their job.

Let’s look at Keith Phillips.

Phillips went to prison in 2010.

Somewhere in there something else bad happened: he was injured and lost almost all vision in his right eye. He filed a civil lawsuit against the prison and received a $201 thousand settlement in 2014. He did not file a tax return for 2014.

Nor would I. Damages for physical injuries are nontaxable, and this sounds very physical to me.

The IRS thought otherwise and wanted almost $52 grand in tax, plus penalties, interest, a safe room, coloring books and a binkie while they worked through the microaggression.

They sent a SNOD.

Phillips had no idea. He was in prison.

The Tax Court rubber-stamped the assessment. The IRS began collection activity. They sent letters to the same address as the SNOD but heard nothing back. They filed a tax lien. They notified the State Department that Phillips was seriously delinquent, and State should begin revoking his passport. That State Department matter was fortunately sent to Phillip’s correct address.

Now Phillips was wondering what had happened, although he had no plans to travel overseas in the near future. He filed with the Tax Court.

IRS:            More than 90 days have passed. We win, you lose. Why? Because you are a loser, you big loser you.  

Phillips:       Hey, IRS, you sent the SNOD to the wrong address.

IRS:            Nope, we sent it to the right address.

Phillips:       I never lived at this address.

IRS:             You did. We have a USPS notice for change of address.

Phillips:       Let me see it.

IRS:             Knock yourself out, loser.

Phillips:       This is my son. We have the same name. He was living with his mom. I had been here … in prison … years before this change of address was sent.

IRS:             Oops.

If the SNOD is sent to the wrong address, then the SNOD is not valid. To the IRS’ credit, this error is not common, but it happens.

Mind you, this does not technically mean that the matter is over. Phillips never filed a return for 2014, so the statute of limitations has never started for that year. On the other hand, now that the IRS is aware that the settlement was for personal injury – and thus nontaxable – what is the point?

Our case this time was Phillips v Commissioner, T.C. Memo 2024-44.

A Firefighter Sues

The taxation of legal settlements can be maddening.

The general rule is found in IRC Section 61, which can be colloquially summarized as:

If it breathes, moves, or eats, it is taxable.

Then come the exceptions.

The Code begins with a broad rule, and then you must find and fit into an exception to avoid taxability. A big exception for legal settlements is Section 104(a)(2):

        § 104 Compensation for injuries or sickness.

(a)  In general.

Except in the case of amounts attributable to (and not in excess of) deductions allowed under section 213 (relating to medical, etc., expenses) for any prior taxable year, gross income does not include-

(1)  amounts received under workmen's compensation acts as compensation for personal injuries or sickness;

(2) the amount of any damages (other than punitive damages) received (whether by suit or agreement and whether as lump sums or as periodic payments) on account of personal physical injuries or physical sickness;

What can we learn here?

(1) The Code does not care whether the judge decides or if the parties instead come to an agreement.  

(2)  It does not care if one gets paid in a lump sum or in a series of payments.

(3) It cares very much that the settlement is for something physical – whether injury or sickness.  

What about something nonphysical, such as mental or emotional distress?

Reviewing the history of the Code helps here, as we learn that the Code was changed in 1996 to clarify that mental and emotional injury settlements are excludable from income only if they arose from physical injury or sickness.

This gives the following rule of thumb:

          Physical               =       nontaxable

          Nonphysical        =       taxable      

The attorney must be aware of the above demarcation and wordsmith accordingly if some or all the settlement is for nonphysical damages. 

Can it be done?

Let’s look at the Montes case.

Suzanne Montes wanted to be a firefighter since she was a little girl. She was one of the few women to pass the exam to get into the San Francisco Fire Academy. She then was one of the few women to graduate from the program.

Good for her.

In 2016 she received a sweet assignment to a firehouse in downtown San Francisco.

You may know that firefighters work as a team and in 24-hour shifts. There are about 10 shifts per month, so they spend a LOT of time together. Suzanne was a woman. The remainder of the team were men. Many did not welcome her. First came the disparaging comments, then sabotaging her equipment, then doing - I do not know what specifically and I do not want to know – “disgusting and extremely unsanitary” things to her personal property and effects.

Thanks, guys, for painting men as knuckle-dragging Neanderthals. Way to represent the team.

She complained.

She sued.

She won approximately $380 grand.

Good.

She went to a CPA when it was time to file. The CPA advised that the $380 grand was not taxable.

Even better.

You know the IRS balked, as we are looking at a Tax Court case.

The IRS’s first argument?

Start with the complaint, which claimed sex discrimination and retaliation, including the intentional infliction of emotional distress.

There are no allegations of physical disease or harm to her in the complaint.”

We are not seeing the magic words here: physical injury, physical sickness or micrato raepy sathonich.

Hopefully her attorney salvaged this in the settlement agreement.

Here is the Court:

Our detective work here begins and ends with the settlement agreement.”

Oh oh.

There are no allegations of physical injury …, and indeed, in the summary of the complaint it says, ‘She has lost compensation for which she would have been entitled. She has suffered from emotional distress, embarrassment, and humiliation and her prospects for career advancement have been diminished.’”

No magic words.

Yep, she lost her case. The settlement was taxable.

The Court did hand her a small victory, though. Penalties did not apply because she took a reasonable position based on the advice of a CPA.

Our case this time was Montes v Commissioner, Docket No. 17332-21, June 29, 2023.

 

"I Never Heard Of The Alternative Minimum Tax"

 

I am looking at a case that involves the alternative minimum tax.

While it still exists, much of the steam has thankfully been taken out of the AMT. It started off as Congressional reaction to a handful of ultrawealthy families paying little to no income taxes decades ago. Congress’s response was to require a second tax calculation, disallowing certain things – such as exemptions for your dependents.

Yes, you read that correctly, you large-family tax scofflaw.

Now, it wouldn’t be so bad if this thing had been scaled to only reach the wealthy and ultrawealthy, but that is not what Congress did. Congress instead gave you a spot, and then you were on your own. For 2017 that spot was approximately $84 grand in income for marrieds filing jointly.

I used to see the AMT as often as a Gibson’s employee sees donuts.

Thankfully the Tax Cut and Jobs Act of 2017 did a couple of things to defang the AMT:

(1) It increased the exemption (that is, the spot) for everyone. Marrieds now have an exemption of approximately $115,000, for example.

(2)  More importantly, it adjusted a previous rule that phased-out the exemption as one’s income increased. For example, marrieds in 2017 would start phasing-out when their income reached approximately $160,000. Now it is over $1 million, which makes a lot more sense it if was truly targeted at the wealthy.

Why the absurdly low previous income thresholds for the AMT, especially since it was supposed to target the “rich?” Think of it as Congressional addiction to paper crack – the paper being your dollar bills.

The tax law is a little saner until 2026, when the TCJA goes “poof.” Much prior tax law will then resurrect – including the previous version AMT.

Robert Colton and Alina Mazwin (R&A) filed a joint return for 2016.

The IRS did its computer matching and sent them a notice. There was $125,000 reported by JP Morgan Chase Bank. The IRS wanted taxes on it.

R&A explained to the IRS that the $125,000 was a legal settlement, and that half of it went to Mr Colton’s ex-spouse.

The IRS said OK, but we want taxes on the $62,500.

Let’s take an aside here. You may have heard that lawsuit settlements are not taxable. That is only partially true. The lawsuit has to involve physical injury (think a car crash, for example) to be tax-free.

It appears that Mr Colton’s settlement was of the non-car crash variety, meaning that it was taxable.

R&A then amended their 2016 return, picking up the $62,500 but also claiming a miscellaneous itemized deduction of $80,075 for attorney fees.

Hah! They might even get a tax refund out of this, right? Take that, IRS.

Except …

Guess what is not deductible for the AMT.

Yep, that miscellaneous itemized deduction.

So – for AMT purposes – their income went up by the $62,500 but there was no deduction for the related legal fee.

How much income did R&A have before the IRS contacted them?

About $40 grand.

Yep, the AMT had been bent so far beyond recognition that it trapped someone amending a return to show perhaps $100 grand in income.

Folks, that income level does not go you invited to the cool parties on Martha’s Vineyard.

Let me share a line from the case:

Petitioners stated in their petition that ‘[they] never heard of [the] alternative minimum tax.”

I get it. I consider it unconscionable that an average person has to hire someone like me to prepare their taxes.  

Our case this time for the home gamers was Colton and Mazwin v Commissioner, T.C. Memo 2021-44.

A Bank Of America Horror Story

A major corporation hounds you almost to the point of death. You sue. You receive a settlement. Is it taxable?

Like so much of tax law, it depends. For example, did the attorney include the magic words that complete the incantation?  

Mr. and Mrs. French received a deficiency notice for their 2012 tax year. The IRS wanted $7,231 in taxes and $1,446 in penalties.

At issue was whether a settlement payment was taxable.

Let’s lay out the story:

·      In 2008 the French’s bought a house.

·      Shortly thereafter Bank of America bought their mortgage.

·      In August, 2009 Bank of America transferred their loan to a subsidiary, BAC Home Loan Servicing.

·      In December, 2009 Mr. and Mrs. French signed a loan modification agreement. The modification was to become effective February 1, 2010.

A loan modification means that that payments were temporarily suspended, an interest rate was changed, the loan term was lengthened and so on. There was a lot of modifications going on around that time.

·      Mrs. French suffered from a very bad back. She was admitted to the hospital in October, 2009 for surgery.

·      From late 2009 into early 2010 Bank of America began calling the French’s on a routine basis, sometimes up to 5 times a day. They were hounding the French’s that their mortgage was about to go into foreclosure.

·      Mr. French was concerned about the effect of these endless calls on his wife. He requested that Bank of America call him on another line, that way he could shield his wife from the stress. Bank of America couldn’t care less. If anything, they were continued receiving multiple calls from multiple people across multiple BAC offices.

·      Mrs. French went into the hospital in December, 2009 and again in January, 2010.

·      In January, 2010 Mr. French spoke with a BAC representative. He explained the loan modification. The representative had no idea what Mr. French was talking about. He explained that – whoever Mr. French sent the modification to – it was not BAC. He instructed Mr. French to redo the paperwork, stop payment on the old check and enclose a new check.

·      After much hassle, Mr. French was told that the modification was accepted and that he should start making payments per the new agreement. He made 10 payments of $1,067.10.

·      When she was finally discharged from the hospital on January 21, 2010, a Bank of America representative called to tell Mrs. French that “officers were on their way to evict” them.

·      On January 23, she started experiencing chest pain and shortness of breath. She went back to the hospital. He suffered two pulmonary emboli, passed away twice but was resuscitated. She was discharged February 4, 2010.

·      BAC did not process the first modification as they promised Mr. French. BAC kept their higher monthly payments and interest rate. To make matters worse, they posted their monthly payments to a non-interest- bearing escrow account and treated the payments as if they were processing fees.

·      In October 2010 BAC told Mr. French that they were not honoring the first modification and that the loan was severely delinquent. They sent a second modification, with conditions and terms injurious to the French’s. For example, the second modification did not even address the 10 payments the French’s had previously sent. Mr. French, his back to a wall, signed the second modification in November, 2010.

·      BAC continued, increasing their monthly payment from $1,067.10 to $1,081.49. In September, 2011, BAC sent the French’s a notice that their checks would not be applied and would instead be returned if not for the higher amount.

Finally, the French’s hired an attorney.

The phone calls stopped.

The French’s sued on six claims, alleging fraud, integration of the first and second loan modifications, punitive damages, additional damages, attorney fees and so forth.

What they did not sue for was personal damages to Mrs. French’s health. 

They settled in 2012. The French’s received $41,333, and the attorneys received $20,666.

The French’s did not report the settlement as income on their 2012 tax return.

The IRS wanted to know why.

The French’s presented several arguments:

(1)  $7,500 of the settlement was not taxable under the “disputed debt” doctrine.

If one party does not agree to the terms of a debt, later settlement does not necessarily mean income. It may mean repayment of amounts improperly charged the borrower, for example. An interesting argument, but the Court noted that the settlement agreement never mentioned disputed or contested debt.

(2)  They were being repaid their own money.

(3)  IRC Section 104(a)(2)

 § 104 Compensation for injuries or sickness.

 (a)  In general.

Except in the case of amounts attributable to (and not in excess of) deductions allowed under section 213 (relating to medical, etc., expenses) for any prior taxable year, gross income does not include-

(1)  amounts received under workmen's compensation acts as compensation for personal injuries or sickness;

(2) the amount of any damages (other than punitive damages) received (whether by suit or agreement and whether as lump sums or as periodic payments) on account of personal physical injuries or physical sickness;

To me, this was – by far – their best argument.

But it is one that BAC would never, ever put in writing.

The Court was however willing to look back to the six claims the attorneys filed for Mr. and Mrs. French. Unfortunately, the only language it found was the following:

… suffered lost time, inconvenience, distress [and] fear, and have been denied the benefit of the loan modification they were promised, and are being charged too much on their loan.”

These, folks, are not the magic words to open the Section 104(a)(2) door. For one thing, the words referred to both Mr. and Mrs. French.

The French’s owed the tax, but the IRS relented on the penalties.

Too bad the attorneys did not run the paperwork past a competent tax practitioner before it was too late.

Our case this time was French v Commissioner, T.C. Summary Opinion 2018-36.

Spouses Owning Businesses, Divorce And Taxes

A fundamental concept in taxation is that an “accession to wealth” represents taxable income, unless the Code says otherwise.

There are limits on this, of course, otherwise you would be immediately taxed when your mutual fund or house went up in value. The Code will (usually) want to see a triggering event, such as a sale, exchange or disposition by other means. You don’t pay tax on your stock gain, for example, until you sell the stock.

But the concept also creates problems. For example, consider the recent development of crowdfunding. You have an idea for the next great breakfast sandwich, and you reach out on the internet for money to get the idea going. You have accession to wealth, but is the money taxable to you? The tax consequence can get very murky very quickly. For example:

·        If you provide investors with breakfast sandwiches, there is an argument that you sold sandwiches.

·        If investors instead receive ownership (say shares of stock), we would sidestep that sale-of-sandwiches thing, but you might have an issue with securities laws.

·        If investors receive nothing, one could argue that the monies were a gift. The closer you get to detached generosity without expectation of economic gain, the better the argument.

Let's next consider accession to wealth in a divorce context. Here is Code Section 1041:

(a) General rule. No gain or loss shall be recognized on a transfer of property from an individual to (or in trust for the benefit of)—

(1) a spouse, or

(2) a former spouse, but only if the transfer is incident to the divorce.

(c) Incident to divorce. For purposes of subsection (a)(2), a transfer of property is incident to the divorce if such transfer— 

(1) occurs within 1 year after the date on which the marriage ceases, or

(2) is related to the cessation of the marriage.

Believe it or not, the general definition of income could trigger when marital assets are divided upon divorce. That makes little sense, of course, so Section 1041 provides an escape clause.

Question: how much time do you have to separate the marital assets?

The first answer provided in (c)(1) is one year. It is immediately followed by (c)(2) which (appears to) expand the answer to any period as long as the asset transfer is related to the cessation of marriage. That is a bit open-ended, so the tax Regulations interpret (c)(2) as up to six years.

The Belots started a dance school in New Jersey in 1989. The wife was the dancer and creative force, while the husband attended to the business side. Eventually they had several dance studios, a corporation to manage them and a partnership to own the real estate. They did well. While owned 100% by the spouses, the husband and wife were not necessarily 50:50 owners in each entity.

They started divorce action in 2006,and adjusted their ownership in each entity to 50:50. The divorce was finalized in January, 2007.

There is a reason they got divorced. Tired of her ex-husband's participation, Ms. Belot bought-out his share in 2008 for $1,580,000.

Mr. Belot took the position that this was not taxable under Section 1041. The IRS took the opposite position and billed him almost $240,000 in tax and penalties.

Off to Tax Court they went.

The IRS argued that each and every transaction had to come under the umbrella of Section 1041. There was no question that the first transaction qualified, but the second transaction – cashing-out Mr. Belot entirely – did not because it represented an event arising after the divorce. The second settlement represented a business contingency and was not related to the divorce decree.

The IRS was following a hyper-technical interpretation of its Regulations.

The problem is that the Code does not say "pursuant to the divorce decree." It instead says "related to the cessation of marriage." The divorce decree is arguably the most vivid expression of such cessation, but it is not the only one. The Belots were clearly still dividing marital assets owned at the time of divorce.

The Court decided in favor of the Belots.

Why did the IRS even pursue this?

The IRS was enforcing the everything-is-taxable position, unless excluded by the Code somewhere. 

JPMorgan's Nondeductible Madoff Deal

On January 7, 2014, JPMorgan entered into a deferred prosecution agreement with the Justice Department. This is another payment in the ongoing Bernie Madoff saga, and the bank agreed to pay a $1.7 billion settlement as well as $350 million to the Office of the Comptroller of the Currency and $543 million to a court-appointed trustee.

Madoff kept significant balances with JPMorgan.  Banks are the first line of defense against fraud, but JPMorgan never filed suspicious activity reports with regulators, even though there were significant reservations as to when they became suspicious. The bank did not admit any criminal activity in the agreement, but it did allow that it missed red flags from the late 1990s to late 2000s.

What caught my eye was the following text from the following joint release by the Manhattan U.S. Attorney and FBI:
           

… JPMorgan agrees to pay a non-tax deductible penalty of $1.7 billion, in the form of a civil forfeiture, which the Government intends….”

This is unusual language.

The tax code provides a tax deduction for all of the ordinary and necessary expenses paid or incurred during the taxable year in carrying on any trade or business.

And then the tax Code starts taking back. One take back is Section 162(f):

162(f) FINES AND PENALTIES.— No deduction shall be allowed under subsection (a) for any fine or similar penalty paid to a government for the violation of any law.

Let’s drill down a little bit into the Regulations:

This prohibition applies to any fines paid by a taxpayer because the taxpayer has been convicted of a crime (felony or misdemeanor) in a full criminal proceeding in an appropriate court.   The prohibition also extends to civil fines if the fines are intended by Congress as punitive in nature.

So, if fines are paid pursuant to a criminal case, then the taxpayer is hosed. However, if fines are paid pursuant to a civil case, there is one more step: are the fines punitive in nature?

Attorneys differentiate damages between those that are remedial and those that are punitive. A remedial payment is intended to compensate the government or another party – to “make one whole,” if you will. It is intended to restore what was disturbed, upset or lost, and not intended as penalty or lashing against the payer.

Let’s complicate it bit. There is a court case (Talley Industries Inc v Commissioner) that allows damages to be deductible if they are remedial in intent, even if labeled as a fine or penalty.

EXAMPLE: The NFL fines a player for unnecessary roughness. The NFL can call this a fine, but it is not a fine per Section 162(f) and will be deductible to the player involved.

You are seeing how this is fertile hunting ground for tax lawyers. Unless the payment is pursuant to a criminal case, odds are good that it is deductible.

Now remember that this agreement is Madoff related, and that there are hard feelings about JPMorgan’s involvement with Madoff over the years, and you can see why the Justice Department included the “nondeductible” language in the agreement.

Let’s take this a step further. Under Talley, JPMorgan could deduct the $1.7 billion on its tax return. Remember, it is not a fine or penalty under Sec 162(f) just because somebody somewhere called it as such.

Would JPMorgan be likely to do this?

This is a “deferred prosecution” agreement.  If JPMorgan did deduct the settlement, they might not have an issue with the IRS, but they would likely have a very sizeable issue with the Justice Department.