Will I Qualify For The Tips Deduction?

 

Can I take advantage of the new tips deduction?

I will be slowing down in 2026: fewer hours, fewer clients, unlikely to accept new clients. It was inevitable, but the events of the last year-plus have accelerated my decision. I was witness to friends and the consequences from their sale of a firm. I do not care to see that again.

Can I do anything in 2026 to catch a tax break?

We are talking about the “No Tax On Tips” provision of the One Big Beautiful Bill signed by the President on July 4, 2025. The break will last four years – beginning in 2025 – and allow a tipped worker to exclude up to $25,000 of “qualified” tips from income taxes.

COMMENT” Yes, the break is retroactive to January 1, 2025 even though the OBBB was not signed until July 4.

COMMENT: The $25 grand is per return. If you file single, the limit is $25 grand. If you file jointly, the limit is again $25 grand. Another important point is that we are talking about federal income taxes only. Those tips are still going to be subject to social security taxes, just like before.

There is an income limit, of course: $150 grand for singles and $300 grand for marrieds.

The break is available whether you are a tipped employee or tipped self-employed. The reporting to you, however, will be different.

If you are an employee, you will receive a 2025 Form W-2 from your employer.

I want you to notice Box 7: Social Security Tips.

The tips deduction uses the term “qualified” tips.

Mind you, it is possible that Box 7 is also the amount for qualified tips, but it does not have to be. The tax Code does this sleight-of-hand repetitively by sliding the word “qualified” before otherwise innocuous nouns. How can a tip be “nonqualified?” Easy: it is nonvoluntary. How does that happen? Again - easy. Say that you have a party of eight or more and the restaurant applies an automatic gratuity of 18%. That fact that the gratuity/tip is now automatically included means that it is nonvoluntary, which means it is not “qualified,” which means it does not qualify for the tips deduction.

So ... how is one to know how much of box 7 is qualified?

Fortunately – and given that the law was passed halfway into the year – the IRS realized that employers and payroll companies could not make these changes retroactively. In Notice 2025-62, the IRS stated that - for 2025 only - an employee can assume that Box 7 is the same amount as qualified tips. Employers can also get this information to employees via other means, such as an online portal.

A new W-2 will be in place for 2026.

What about tipped self-employeds?

Now we are circling back to my situation and the tips deduction.

Scratch that Form W-2, as I will not be an employee. I may get some flavor of Form 1099, though.

Form 1099-K         used for credit and debit cards

Form 1099-NEC    used for independent contractor

Form 1099-MISC  used for other reportable payments

I took a look: nope, not seeing any 2025 reporting for tips. I see something on Form 1099-MISC Box 10 for payments to an attorney, but I am not an attorney. The IRS has said, however, that they are revising the 2026 forms to include tips information. That's OK, I will adjust my 2026 invoices as necessary - if I can otherwise qualify for the deduction.

I gotta ask: how will the IRS know if I am self-employed and have 2025 income representing qualified tips?

I see the following IRS guidance: “you can rely on your own tip records.”

Not the hardest tax planning I have seen.

The IRS buttressed this with proposed Regulations on September 22, 2025.

I see four requirements in the Regulations for a qualified tip:

·      Is paid voluntarily

·      Is not received in a specified trade or business

·      Satisfies other requirements established by the Secretary

·      Received in an occupation that customarily and regularly received tips on or before December 31, 2024

Let’s see:

·      I can meet this: you can pay me voluntarily or involuntarily, but you will pay me.

·      This is a problem. I am not going to labor you with the provenance and metaphysics of “specified trades or businesses,” other than to say that common examples include physicians, attorneys, and accountants.

o   But there is transitional relief until January 1 “of the first calendar year following the issuance of final regulations ….”

§  I may still be in the running.

·      I will worry about other requirements when they happen.

·      We hit a hard stop with “customarily and regularly received tips.”

o   The IRS published a list of qualifying occupations.

o   I see the expected: bartenders, wait staff, hair stylists, and so forth.

o   I see a few unexpected: home landscapers, electricians, and plumbers.

o   I see nothing for accountants and tax preparers.

o   I do see something for “#209 Digital Content Creators.”

§  I suppose I could put these blogs on YouTube and be a “content creator.”

I am not seeing a (reasonable) way to meet that fourth requirement and get my 2026 fees to qualify for the tips deduction, unfortunately. I suppose an occasional client might mark my fee as a “tip” – thereby hoping to help me out – but I am not seeing a way to sidestep (at least legitimately) the “customarily and regularly” hurdle.

I won’t, but you know somebody will.

The tax literature is littered with cases like these.

Is This Reasonable?

 

I have long maintained that the IRS is unreasonable by repeatedly disallowing reasonable cause exception to its numerous penalties. Their standard appears to allow little to no room for real-world variables – someone got sick, someone misunderstood the requirements (wow, how could that happen?), technology broke down, and so on.

Mind you, I say this after contacting the IRS – AGAIN – about returns we filed for two clients. In each case the IRS has misplaced the returns, failing its mission, causing needless (and incorrect) notices, and embarrassing us as practitioners. One of these returns will soon celebrate its one-year anniversary. The IRS has had plenty of time to investigate and resolve the matter. I have, and I am just one guy.

However, have a practitioner send a tax return two minutes after midnight on an extended due date and the IRS will penalize his/her tax practice to near bankruptcy. It may be that there was no electricity in the office until that very moment. No matter: there is no reasonable cause for things not functioning perfectly every time every place all the time.

The hypocrisy is almost suffocating. Let’s make the relationship reciprocal – for example, let me send the IRS an invoice for wasting my time – and see how quickly the IRS recoils in terror.

Let’s talk about RSBCO’s recent shout-out to the Supreme Court.

RSBCO was a wealth management company headquartered in Louisiana. It hired someone (let’s call him Smith) with a background in accounting to spearhead its IRS information reporting.

Smith took RSBCO successfully through one filing season.

Unbeknownst to anyone, however, Smith was fighting some dark demons, and the second filing season did not go as well.

Smith unfortunately waited until the final day to electronically file approximately 20,000 information returns using the IRS FIRE system. FIRE sent an automated e-mail that certain files had errors preventing them from being processed and RSBCO should send replacement files. The e-mail went only to Smith, so no one else at RSBCO knew.

Smith – approximately four months later – was able to resume work. He had been diagnosed with clinical depression, having suicidal ideation, and struggling to focus and complete tasks at work.

COMMENT: I am thinking Reg 301.6724-1(c):

(c) Events beyond the filer's control

(1) In general. In order to establish reasonable cause under this paragraph (c)(1), the filer must satisfy paragraph (d) of this section and must show that the failure was due to events beyond the filer's control. Events which are generally considered beyond the filer's control include but are not limited to—

(iv) Certain actions of an agent (as described in paragraph (c)(5) of this section),

Smith saw the e-mails. He corrected the information returns.

QUESTION: What were the errors about? About dashes, that’s what. The IRS wanted dashes added or removed. Approximately 99% of the problem was little more than a spelling bee.

Smith had a successful third filing season.

Except for the $579,198 penalty notice the IRS sent for the information returns from season two.

COMMENT: Methinks that is a bit harsh for not winning a spelling bee.

Smith was still battling his health issues. He hid the penalty notice in his desk.

A few months later RSBCO let Smith go.

The new hire soon found the notice and tried to contact the IRS. The contact number provided was entirely automated, so the hire could never speak with a human being.

COMMENT: Been there, pal.

The IRS – thinking they had been ignored – sent a Final Notice. RSBCO requested a Due Process Hearing.

The Hearing Officer for the CDP hearing mostly waived off RSBCO’s side of the story. After a Solomonic 15-minute reflection, the Officer did offer to abate 25% of the penalty amount.

COMMENT: It’s something.

RSBCO had to decide how to proceed. They decided to pay the IRS $579 grand and pursue the refund administratively.

In December 2018 RSBCO filed a Claim for Refund.

The IRS received it. And then lost it.

Uh huh.

In August 2019 RSBCO filed a lawsuit.

In June 2020 – after irritating the court – the IRS promised RSBCO that it would play fair if they refiled the claim.

RSBCO agreed and withdrew the lawsuit.

In September it filed its Claim for Refund … again.

And the IRS lost it … again.

COMMENT: You see what is going on here, don’t you?

In May 2021 RSBCO filed a second lawsuit in district court.

In September 2022, the jury decided that RSBCO had reasonable cause for penalty abatement.

COMMENT: Will this ever end?

The IRS processed the refund … wait … no, no … that’s wrong. The IRS appealed the district court decision to the Fifth Circuit.

The Fifth Circuit found that jury instructions were flawed. The district court stated that an employee’s mental health - by itself - did not give rise to reasonable cause. The jury was not properly instructed.

QUESTION: I guess the following by the district court judge was unclear to the IRS, which DID NOT object:

Anything else? Anybody want to put your objection [to jury charges] on the record if you’d like objecting to them?”

COMMENT: I can see the confusion. Making out this question is like trying to plumb the metaphysics of James Joyce’s Ulysses. No wonder the IRS failed to object.

In October 2023 RSBCO petitioned the Supreme Court.

Which just declined the petition.

Meaning the Fifth Circuit has the final word.

The Fifth Circuit wants a new trial.

Will this nightmare ever end?

It is … unreasonable.

Our case this time was RSBCO v U.S., US Supreme Court Docket 24-561.

Caleb William’s NFL Contract

 It may be that the NFL saved him from bad tax advice.

We are talking about Caleb Williams, the 2024 NFL number one overall draft pick by the Chicago Bears. He signed a four-year fully guaranteed contract for $39.5 million.

I can only wish.

But it was two additional negotiating positions that caught my eye.

(1)  He wanted to be paid via an LLC.

(2)  He wanted some/all of his contract to be structured as a forgivable loan.

I read that he was represented by his father, who has experience in commercial real estate but is not a registered agent.

But it helps to explain the LLC. The use of LLCs for real estate is extremely common, so his father would have seen their use repetitively. Still, what is the point of an LLC with an NFL contract?

It might be the expenses that an NFL player might incur: agent fees, union dues, specialized training and related travel, certain therapies and so forth. As those receiving a W-2 know, employee business expenses are presently nondeductible. If Caleb could run his NFL earnings through an LLC, perhaps he could avoid employee business expense classification and deduct them instead as regular business expenses.

There is a hitch, though. None of the four major team sports will pay compensation to an entity rather than directly to the athlete. In contrast, non-team athletes – like golfers – can route their earnings through a business entity. A key difference is that the PGA considers its golfers to be independent contractors, whereas the NFL (or MLB, NBA, or NHL) considers its players to be employees.

There is speculation that Caleb may have preferred an LLC because LLCs – ahem – “do not file tax returns.”   

Not quite. The tax treatment of LLCs is quite straightforward:

(1)  If the LLC has partners, then it will file a partnership return.

(2)  If the LLC elects to be taxed as a corporation, then it will file a corporate return. If an S election in place, it will file an S corporation return.

(3)  If the LLC has a single member, then the LLC is disregarded and does not file a tax return.

Do not misunderstand that last one: it does not say that income belonging to the LLC does not land on a tax return.

Let’s say that Caleb created a single member LLC (SMLLC). SMLLCs are also referred to as disregarded entities. The tax  Code instead considers Caleb and his SMLLC to be the same taxpayer. That is why there is no separate LLC return: all the income would be reportable on Caleb’s personal return.

Could someone have read the above and thought that income routed through an SMLLC is not taxed at all?

If so, Caleb really needs to hire a tax professional yesterday.

What about the loan forgiveness proposal?

I get it: loans are normally not considered income, as any increase in wealth is immediately offset by an obligation to repay the loan.

OK, Caleb receives contract monies, but he is liable for their repayment to the NFL. This potential liability means no immediate income to him. He would have income when the loan is forgiven, and (hopefully) he has some control when that happens.

But the NFL can call his loan, meaning he then must repay.

Oh puhleeeze.

Not to worry, says whoever. The NFL has no intention of calling the loan.

I am a huge NFL fan, but I am not an NFL team owner fan. There is no way I am trusting my money to owners who are monetizing their sport to such a degree that many fans cannot even see the games. Seriously, how many streaming services do they think an average person can afford?

What if Caleb includes conditions and guarantees and collateral and puts and ….?

Listen to yourself. You are leaving loan-land and whatever tax idea you started with. The IRS will come to the same conclusion. You have accomplished nothing, and you may even be exposing yourself to fraud charges.

I suppose Caleb could structure it as deferred compensation, the way Shohei Ohtani did with the Los Angeles Dodgers. Deferred compensation can get into crazy tax tripwires, but at least we are no longer talking about loans. If this is what he wants, then drop the loan talk and negotiate deferred compensation.

That is BTW what I would do. There is enough money here to make Caleb rich both now and later.

The NFL did Caleb Williams a favor by shooting down both proposals. 

Failing To Take A Paycheck

I am looking at a case involving numerous issues. The one that caught my attention was imputed wage income from a controlled company in the following amounts:

2004                    $198,740

2005                    $209,200

2006                    $220,210

2007                    $231,800

2008                    $244,000

Imputed wage income means that someone should have received a paycheck but did not.

Perhaps they used the company to pay personal expenses, I think to myself, and the IRS is treating those expenses as additional W-2 income. Then I see that the IRS is also assessing constructive dividends in the following amounts:

2004                    $594,170

2005                    $446,782

2006                    $375,246

2007                    $327,503

2008                    $319,854 

The constructive dividends would be those personal expenses.

What happened here?

Let’s look at the Hacker case.

Barry and Celeste Hacker owned and were the sole shareholders of Blossom Day Care Centers, Inc., an Oklahoma corporation that operated daycare centers throughout Tulsa. Mr. Hacker also worked as an electrician, and the two were also the sole shareholders of another company - Hacker Corp (HC).

The Hackers were Blossom’s only corporate officers. Mrs. Hacker oversaw the workforce and directed the curriculum, for example, and Mr. Hacker was responsible for accounting and finance functions.

Got it. She sounds like the president of the company, and he sounds like the treasurer.

For the years at issue, the Hackers did not take a paycheck from Blossom.

COMMENT: In isolation, this does not have to be fatal.

Rather than pay the Hackers directly, Blossom made payments to HC, which in turn paid wages to the Hackers.

This strikes me as odd. Whereas it is not unusual to select one company out of several (related companies) to be a common paymaster, generally ALL payroll is paid through the paymaster. That is not what happened here. Blossom paid its employees directly, except for Mr. and Mrs. Hacker.

I am trying to put my finger on why I would do this. I see that Blossom is a C corporation (meaning it pays its own tax), whereas HC is an S corporation (meaning its income is included on its shareholders’ tax return). Maybe they were doing FICA arbitrage. Maybe they did not want anyone at Blossom to see how much they made.  Maybe they were misadvised.

Meanwhile, the audit was going south. Here are few issues the IRS identified:

(1)  The Hackers used Blossom credit cards to pay for personal expenses, including jewelry, vacations, and other luxury items. The kids got on board too, although they were not Blossom employees.

(2)  HC paid for vehicles it did not own used by employees it did not have. We saw a Lexus, Hummer, BMW, and Cadillac Escalade.

(3) Blossom hired a CPA in 2007 to prepare tax returns. The Hackers gave him access to the bank statements but failed to provide information about undeposited cash payments received from Blossom parents.

NOTE: Folks, you NEVER want to have “undeposited” business income. This is an indicium of fraud, and you do not want to be in that neighborhood.

(4)  The Hackers also gave the CPA the credit card statements, but they made no effort to identify what was business and what was family and personal. The CPA did what he could, separating the obvious into a “Note Receivable Officer” account. The Hackers – zero surprise at this point in the story - made no effort to repay the “Receivable” to Blossom.  

(5) Blossom paid for a family member’s wedding. Mr. Hacker called it a Blossom-oriented “celebration.”  

(6) In that vein, the various trips to the Bahamas, Europe, Hawaii, Las Vegas, and New Orleans were also business- related, as they allowed the family to “not be distracted” as they pursued the sacred work of Blossom.

There commonly is a certain amount of give and take during an audit. Not every expense may be perfectly documented. A disbursement might be coded to the wrong account. The company may not have charged someone for personal use of a company-owned vehicle. It happens. What you do not want to do, however, is keep piling on. If you do – and I have seen it happen – the IRS will stop believing you.

The IRS stopped believing the Hackers.

Frankly, so did I.

The difference is, the IRS can retaliate.

How?

Easy.

The Hackers were officers of Blossom.

Did you know that all corporate officers are deemed to be employees for payroll tax purposes? The IRS opened a worker classification audit, found them to be statutory employees, and then went looking for compensation.

COMMENT: Well, that big “Note Receivable Officer” is now low hanging fruit, isn’t it?

Whoa, said the Hackers. There is a management agreement. Blossom pays HC and HC pays us.

OK, said the IRS: show us the management agreement.

There was not one, of course.

These are related companies, the Hackers replied. This is not the same as P&G or Alphabet or Tesla. Our arrangements are more informal.

Remember what I said above?

The IRS will stop believing you.

Petitioner has submitted no evidence of a management agreement, either written or oral, with Hacker Corp. Likewise, petitioner has submitted no evidence, written or otherwise, as to a service agreement directing the Hackers to perform substantial services on behalf of Hacker Corp to benefit petitioner, or even a service or employment agreement between the Hackers and Hacker Corp.”

Bam! The IRS imputed wage income to the Hackers.

How bad could it be, you ask. The worst is the difference between what Blossom should have paid and what Hacker Corp actually paid, right?

Here is the Court:

Petitioner’s arguments are misguided in that wages paid by Hacker Corp do not offset reasonable compensation requirements for the services provided by petitioner’s corporate officers to petitioner.”

Can it go farther south?

Respondent also determined that petitioner is liable for employment taxes, penalties under section 6656 for failure to deposit tax, and accuracy-elated penalties under section 6662(a) for negligence.”

How much in penalties are we talking about?

2005                    $17,817

2006                    $18,707

2007                    $19,576

2008                    $20,553

I do not believe this is a case about tax law as much as it is a case about someone pushing the boundary too far. Could the IRS have accepted an informal management agreement and passed on the “statutory employee” thing? Of course, and I suspect that most times out of ten they would. But that is not what we have here. Somebody was walking much too close to the boundary - if not walking on the fence itself - and that somebody got punished.

Our case this time was Blossom Day Care Centers, Inc v Commissioner, T.C. Memo 2021-86.

Renting a Home Office To An Employer

A client asked about the home office deduction last week.

This deduction has lost much of its punch with the Tax Cuts and Jobs Act of 2017. The reason is that employee home office deductions are a miscellaneous itemized deduction, and most miscellaneous itemized deductions have been banned for the next two-plus years. 

The deduction still exists for self-employeds, however, including partners in a partnership or members in an LLC. Technically there is one more hoop for partners and members, but let’s skip that for now.

Say you are working from home. You have a home office, and it seems to pass all the bells-and-whistles required for a tax deduction. Can you deduct it?

Depends. On what? On how you are compensated.

(1) If you are a W-2 employee, then you have no deduction.

(2) If you receive a 1099 (think gig worker), then you have a deduction.

Seems unfair.

Can we shift those deductions to the W-2 employer? Would charging rent be enough to transform the issue from being an employee to being a landlord?

There was a Tax Court case back in the 1980s involving the tax director of a public accounting firm in Phoenix (Feldman). His position involved considerable administrative work, a responsibility difficult to square with being accessible to staff at work while also maintaining confidentiality on private firm matters.

Feldman built a house, including a dedicated office.  He worked out an above-market lease with his firm. He then deducted an allocable share of everything he could against that rent, including maid service.

No surprise, Feldman and the IRS went to Tax Court.

Let’s look at the Code section under dispute:

Sec 280A Disallowance of certain expenses in connection with business use of home, rental of vacation homes, etc.

(a)  General rule.

Except as otherwise provided in this section, in the case of a taxpayer who is an individual or an S corporation, no deduction otherwise allowable under this chapter shall be allowed with respect to the use of a dwelling unit which is used by the taxpayer during the taxable year as a residence.

Thanks for the warm-up, said Feldman., but let’s continue reading:

      Sec 280A(c)(3) Rental use.

Subsection (a) shall not apply to any item which is attributable to the rental of the dwelling unit or portion thereof (determined after the application of subsection (e).

I am renting space to the firm, he argued. Why are we even debating this?

The lease is bogus, said the IRS (the “respondent”).

Respondent does not deny that under section 280A a taxpayer may offset income attributable to the rental of a portion of his home with the costs of producing that rental income. He contends, however, that the rental arrangement here is an artifice arranged to disguise compensation as rental income in order to enable petitioner to avoid the strict requirements of section 280A(c)(1) for deducting home office expenses. Because there was no actual rental of a portion of the home, argues respondent, petitioner must qualify under section 280A(c)(1) before he may deduct the home office expenses.

Notice that the IRS conceded that Feldman was reading the Code correctly. They instead were arguing that he was violating the spirit of the law, and they insisted the Court should observe the spirit and not the text.

The IRS was concerned that the above-market rent was disguised compensation (which it was BTW). Much of tax practice is follow-the-leader, so green-lighting this arrangement could encourage other employers and employees to shift a portion of their salaries to rent. This would in turn free-up additional tax deductions to the employee - at no additional cost to the employer but at a cost to the fisc.

The IRS had a point. As a tax practitioner, I would use this technique - once blessed by the Court – whenever I could.

The Court adjusted for certain issues – such as the excess rent – but decided the case mostly in Feldman’s favor.

The win for practitioners was short-lived. In response Congress added the following to the Code:

      (6)  Treatment of rental to employer.

Paragraphs (1) and (3) shall not apply to any item which is attributable to the rental of the dwelling unit (or any portion thereof) by the taxpayer to his employer during any period in which the taxpayer uses the dwelling unit (or portion) in performing services as an employee of the employer.

An employer can pay rent for an employee’s office in home, said Congress, but we are disallowing deductions against that rental income.

Our case this time was Feldman v Commissioner, 84 T.C. 1 (U.S.T.C. 1985).

 

A Ghost Preparer Story

 

I came across a ghost preparer last week.

I rarely see that.

A ghost preparer is someone who prepares a tax return for compensation (me, for example) but who does not sign the return.

This is a big no-no in tax practice. The IRS requires all paid tax preparers to obtain an identification number (PTIN, pronounced “pea tin”) and disclose the same on returns. The IRS can track, for example, how many returns I signed last year via my PTIN. There are also mandates that come with the CPA license.

Why does the ghost do this?

You know why.

It started with a phone call.

Client: What do you know about the employee retention credit?

Me: Quite a bit. Why do you ask?”

Client: I had someone prepare refunds, and I want to know if they look right.”

You may have heard commercials for the ERC on the radio These credits are “for up to $26,000 per employee” but you “must act now.”

Well, yes, it can be up to $26,000 per employee. And yes, one should act soon, because the ERC involves amending tax returns. Generally, one has only three years to amend a return before the tax period closes. This is the statute of limitations, and it is both friend and foe. The IRS cannot chase you after three years, but likewise you cannot amend after the same three years.

The ERC was in place for most of 2020 and for 9 months of 2021. If you are thinking COVID stimulus, you are right. The ERC encouraged employers to retain employees by shifting some of the payroll cost onto the federal government.

Me: I thought you did not qualify for the ERC because you could not meet the revenue reduction.” 

         Client: They thought otherwise.”

         Me: Send it to me.”

He did.

I saw refunds of approximately $240,000 for 2020. I also remember our accountant telling me that the client could not meet the revenue reduction test for 2020. Revenues went down, yes, but not enough to qualify for the credit.

COMMENT: There are two ways to qualify for the ERC: revenue reduction or the mandate. The revenue reduction is more objective, and it requires a decrease in revenue from 2019 (50% decrease for the 2020 ERC; 20% decrease for the 2021 ERC). The second way – a government COVID mandate hobbling the business – does not require revenue reduction but can be more difficult to prove. A restaurant experiencing COVID mandates could prove mandate relatively easily. By contrast, a business experiencing supply-chain issues probably experienced COVID mandates indirectly. The business would likely need its suppliers’ cooperation to show how government mandates closed their (i.e., the suppliers’) doors.

I had our accountant locate the 2020 accounting records. We reviewed the revenue reduction.

The client did not make it.

I called.

Me: Did they say that you qualified under the mandate test?"

         Client: They said I qualified under revenue reduction."

         Me: But you don’t. How could they not tell?"

         Client: Because they never looked at it."

         Me: Then how ….?"

Client: They asked if I had a revenue decline and I said yes. They took my answer and ran with it."

Why would someone do this?

Because that someone works on commission.

There is incentive to maximize the refund, whether right or not.

I was looking at a refund of almost a quarter million dollars.

That would have been a nice commission.

No, the client is not filing those amended returns. He realized the con. He also realized that he had no argument upon IRS audit. He would have to return the money, plus whatever penalties they would layer on. I could no more save him than I could travel to Mars.

He now also understands why they never signed those returns.

Ghosts.

Can A Severance Be A Gift?

I am looking at a case wondering why a tax practitioner would take it to Tax Court.

Then I noticed that it is a pro se case.

We have talked about this before: pro se means that the taxpayer is representing himself/herself. Technically that is not correct (for example, someone could drag me in and still be considered pro se), but it is close enough for our discussion.

Here is the issue:

Can an employer make a nontaxable gift to an employee?

Jennifer Fields thought so.

She worked at Paragon Canada from 2009 to 2017. Apparently, she was on good terms with her boss, as the company …

·      Wired her 35,000 Canadian dollars in 2012

·      Wired her $53,020 in 2014 to help with the down payment on a house in Washington state.

I am somewhat jealous. I am a career CPA, and CPA firms are not known for … well, doing what Paragon did for Jennifer.

She separated from Paragon in 2017.

They discussed a severance package.

Part of the package was forgiveness of the loan arising from those wires.

Forgiveness here does not mean what it means on Sunday. The company may forgive repayment, but the IRS will still consider the amount forgiven to be taxable income. The actual forgiveness is therefore the after-tax amount. If one’s tax rate is 25%, then the actual forgiveness would be 75% of the amount forgiven. It is still a good deal but not free.

Paragon requested and she provided a Form W-9 (the form requesting her social security number).

Well, we know that she will be getting a W-2 or a 1099 for that loan.

A W-2 would be nice. Paragon would pick-up half of the social security and Medicare taxes. If she is really lucky, they might even gross-up her bonus to include the taxes thereon, making the severance as financially painless as possible.

She received a 1099.

Oh well.

She left the 1099 off her tax return.

The IRS computers caught it.

Because … of course.

Off to Tax Court they went.

This is not highbrow tax law, folks. She worked somewhere. She received a paycheck. She left work. She received a final paycheck. What is different about that last one?

·      She tried to get Paragon to consider some of her severance as a gift.

The Court was curt on this point. You can try to be a bird, but you better not be jumping off tall buildings thinking you can fly.

·      She was good friends with her boss. She produced e-mails, text messages and what-not.

That’s nice, said the Court, but this is a job. There is an extremely high presumption in the tax Code that any payment to an employee is compensatory.

But my boss and I were good friends, she pressed. The law allows a gift when the relationship between employer and employee is personal and the payment is unrelated to work.

Huh, I wonder what that means.

Anyway, the Court was not buying:

Paragon’s inclusion of the disputed amount in the signed and executed severance agreement and the subsequent issuance of a Form 1099-MISC indicates that the payments were not intended to be a gift.”

She really did not have a chance.

The IRS also wanted penalties. Not just your average morning-drive-through penalties, no sir. They wanted the Section 6662(a) “accuracy related” penalty. Why? Well, because that penalty is 20%, and it is triggered if the taxpayer omits enough income to underpay tax by the greater of $5 grand or 10% of what the tax should have been.

Think biggie size.

The Court agreed on the penalty.

I was thinking what I would have done if Jennifer had been my client.

First, I would have explained that her chance of winning was almost nonexistent.

COMMENT: She would have fired me then, realistically.

Our best course would be to resolve the matter administratively.

I want the penalties dropped.

That means we are bound for Appeals. There is no chance of getting that penalty dropped before then.

I would argue reasonable cause. I would likely get slapped down, but I would argue. I might get something from the Appeals Officer.

Our case this time was Fields v Commissioner, T.C. Summary Opinion 2022-22.