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. 

Ohtani’s New Baseball Contract

I was reading about Shohei Ohtani’s new contract with the Las Angeles Dodgers. If the name rings a bell, that is because he both bats and pitches. He is today’s Babe Ruth. He played with the Los Angeles Angels in 2023, led the American League with 44 home runs and pitched over 130 innings with a 3.14 ERA.

I am more an NFL than an MLB fan these days, but it is hard to ignore this guy’s athletic chops. It is also hard to ignore his new contract.

•  Contract totals at $700 million
•  He will draw “only” $2 million for the first 10 years.
•  He will draw the deferral (that is, $68 million annually) beginning in 2034 and through 2043.

At $700 million, Ohtani’s is the largest MLB contract ever, but what caught my eye was deferring 98% of the contract for over a decade. Do not be concerned about his cash flow, however. $2 million a year is sweet (that is way over CPA bank), and I understand that his endorsements alone may exceed $50 million annually. Cash flow is not a problem.

Why would Ohtani do this?

For one, remember that athletes at his level are hyper-competitive. There is something about saying that you received the largest contract in MLB history.

Why would the Dodgers do this?

A big reason is the time value of money. $100 ten years from now is worth less than $100 today. Why? Because you can invest that $100 today. With minimal Google effort, I see a 10-year CD rate of 3.8%. Invest that $100 at 3.8% and you will have a smidgeon more than $145 in ten years. Invest in something with a higher yield and it will be worth even more.

Flip that around.

What is $100 ten years from now worth today?

Let’s make it easy and assume the same 3.8%. What would you have to invest today to have $100 in ten years, assuming a 3.8% return?

Around $70.

Let’s revisit the contract considering the above discussion.

Assuming 10 years, 3.8% and yada yada, Ohtani’s contract is worth about 70 cents on today’s dollar. So, $700 million times 70% = $490 million today.

My understanding is the experts considered Ohtani’s market value to be approximately $45 million annually, so our back-of-the-envelope math is in the ballpark.

Looks like the Dodgers did a good job.

And deferring all that money frees cash for the Dodgers to spend during the years Ohtani is on the team and playing. He may be today’s Ruth, but he cannot win games by himself.

There is one more thing …

This is a tax blog, so my mind immediately went to the tax angle – federal or state – of structuring Ohtani’s contract this way.

Take a look at this bad boy from California Publication 1005 Pension and Annuity Guidelines:

          Nonresidents of California Receiving a California Pension

In General

California does not impose tax on retirement income received by a nonresident after December 31, 1995. For this purpose, retirement income means any income from any of the following:

• A private deferred compensation plan program or arrangement described in IRC Section 3121(v)(2)(C) only if the income is either of the following:

1.    Part of a series of substantially equal periodic payments (not less frequently than annually) made over the life or life expectancy of the participant or those of the participant and the designated beneficiary or a period of not less than 10 years.

Hmmm. “Substantially equal periodic payments” … and “a period of not less than 10 years.”

Correlation is not causation, as we know. Still. Highly. Coincidental. Just. Saying.

Ohtani is 29 years old. 98% of his contract will commence payment when he is 40 years old. I doubt he will still be playing baseball then. I doubt, in fact, he will still be in California then. He might return to Japan, for example, upon retirement.

That is what nonresident means.

Let me check something. California’s top individual tax rate for 2024 is 14.4%.

COMMENT: Seriously??

Quick math: $680 million times 98% times 14.4% equals $95.96 million.

Yep, I’d be long gone from California.

 

Can You Have Income From Life Insurance?

 

I was looking at a recent case wondering: why did this even get to court?

Let’s talk about life insurance.

The tax consequences of life insurance are mostly straightforward:

(1) Receiving life insurance proceeds (that is, someone dies) is generally not an income-taxable event.

(2) Permanent insurance accumulates reserves (that is, cash value) inside the policy. The accumulation is generally not an income-taxable event.

(3) Borrowing against the cash value of a (permanent) insurance policy is generally not an income-taxable event.

Did you notice the word “generally?” This is tax, and almost everything has an exception, if not also an exception to the exception.

Let’s talk about an exception having to do with permanent life insurance.

Let’s time travel back to 1980. Believe it or not, the prime interest rate reached 21.5% late that year. It was one of the issues that brought Ronald Reagan into the White House.

Some clever people at life insurance companies thought they found a way to leverage those rates to help them market insurance:

(1)  Peg the accumulation of cash value to that interest rate somehow.

(2)  Hyperdrive the buildup of cash value by overfunding the policy, meaning that one pays in more than needed to cover the actual life insurance risk. The excess would spill over into cash value, which of course would earn that crazy interest rate.

(3)  Remind customers that they could borrow against the cash value. Money makes money, and they could borrow that money tax-free. Sweet.

(4)  Educate customers that – if one were to die with loans against the policy – there generally would be no income tax consequence. There may be a smaller insurance check (because the insurance is diverted to pay off the loan), but the customer had the use of the cash while alive. All in all, not a bad result – except for the dying thing, of course.

You know who also reads these ads?

The IRS.

And Congress.

Neither were amused by this. The insurance whiz kids were using insurance to mimic a tax shelter.

Congress introduced “modified endowment contracts” into the tax Code. The acronym is pronounced “meck.”

The definition of a MEC can be confusing, so let’s try an example:

(1)  You are age 48 and in good health.

(2)  You buy $4,000,000 of permanent life insurance.  

(3)  You anticipate working seven more years.

(4)  You ask the insurance company what your annual premiums would be to pay off the policy over your seven-year window.

(5)  The company gives you that number.

(6)  You put more than that into the policy over the first seven years.

I used seven years intentionally, as a MEC has something called a “7 pay test.” Congress did not want insurance to morph into an investment, which one could do by stuffing extra dollars into the policy. To combat that, Congress introduced a mathematical hurdle, and the number seven is baked into that hurdle.     

If you have a MEC, then the following bad things happen:

(1) Any distributions or loans on the policy will be immediately taxable to the extent of accumulated earnings in the policy.

(2) That taxable amount will also be subject to a 10% penalty if one is younger than age 59 ½.

Congress is not saying you cannot MEC. What it is saying is that you will have to pay income tax when you take monies (distribution, loan, whatever) out of that MEC.

Let’s get back to normal, vanilla life insurance.

Let’s talk about Robert Doggart.

Doggart had two life insurance contracts with Prudential Insurance. He took out loans against the two policies, using their cash value as collateral.

Yep. Happens every day.

In 2017 he stopped paying premiums.

This might work if the earnings on the cash value can cover the premiums, at least for a while. Most of the time that does not happen, and the policy soon burns out.

Doggart’s policies burned out.

But there was a tax problem. Doggart had borrowed against the policies. The insurance company now had loans with no collateral, and those loans were uncollectible.   

You know there is a 1099 form for this.

Doggart did not report these 1099s in his 2017 income. The IRS easily caught this via computer matching.

Doggart argued that he did not have income. He had not received any cash, for example.

The Court reminded him that he received cash when he took out the loans.

Doggart then argued that income – if income there be - should have been reported in the year he took out the loans.

The Court reminded him that loans are not considered income, as one is obligated to repay. Good thing, too, as any other answer would immediately shut down the mortgage industry.  

The Court found that Doggart had income.

The outcome was never in doubt.

But why did Doggart allow the policies to lapse in 2017?

Because Doggart was in prison.

Our case this time was Doggart v Commissioner, T.C. Summary Opinion 2023-25.

Downside Of Not Issuing 1099s

Let’s be honest: no one likes 1099s.

I get it. The government has conscripted us – business owners and their advisors – into unpaid volunteers for the IRS. Perhaps it started innocently enough, but with the passage of years and the accretion of reporting demands, information reporting has become a significant indirect tax on businesses.

It’s not going to get better. There is a proposal in the White House’s Green Book, for example, mandating banks to report gross deposit and disbursement account information to the Treasury.

Back to 1099s.

You see it all the time: one person pays another in cash with no intention – or ability – to issue a 1099 at year-end.

What can go wrong?

Plenty.

Let’s look at Adler v Commissioner as an example.

Peter Adler owned a consulting company. He had a significant client. He would travel for that client and be reimbursed for his expenses.

The accounting is simple: offset the travel expenses with the reimbursements. Common sense, as the travel expenses were passed-on to the client.

However, in one of the years Peter incurred expenses of approximately $44 thousand for construction work.

The Court wondered how a consultant could incur construction expenses.

Frankly, so do I.

For one reason or another Peter could not provide 1099s to the IRS.

One possible reason is that Peter made his checks out to a corporation. One is not required to issue 1099s to an incorporated business. Peter could present copies of the cancelled checks. He could then verify the corporate status of the payee on the secretary of state’s website.

Nah, I doubt that was the reason.

Another possibility is that Peter got caught deducting personal expenses. Let’s assume this was not the reason and continue our discussion.

A third possibility is that Peter went to the bank, got cash and paid whoever in cash. Paying someone in cash does not necessarily mean that you will not or cannot issue a 1099 at year-end, but the odds of this happening drop radically.

Peter had nothing he could give the Court. I suppose he could track down the person he paid cash and get a written statement to present the Court.

Rigghhhtttt ….

The Court did the short and sweet: they disallowed the deduction.

Could it get worse?

Fortunately for Peter, it ended there, but – yes – it can get worse.

What if the IRS said that you had an employee instead of a contractor? You are now responsible for withholdings, employer matching, W-2s and so on.

COMMENT: You can substitute “gig worker” for contractor, if you wish. The tax issues are the same.

Folks, depending upon the number of people and dollars involved, this could be a bankrupting experience.

Hold on CTG, say you. Isn’t there a relief provision when the IRS flips a contractor on you?

There are two.

I suspect you are referring to Section 530 relief.

It provides protection from an IRS flip (that is, contractor to employee) if three requirements are met:

1.    You filed the appropriate paperwork for the relationship you are claiming exists with the service provider.

2.    You must be consistent. If Joe and Harry do the same work, then you have to report Joe and Harry the same way.

3.    You have to have a reasonable basis for taking not treating the service provider as an employee. The construction industry is populated with contractors, for example.

You might be thinking that (3) above could have saved Peter.

Maybe.

But (1) above doomed him.

Why?

Because Peter should have issued a 1099. He had a business. A business is supposed to issue a 1099 to a service provider once payments exceed $600.

There was no Section 530 relief for Peter.

I will give you a second relief provision if the IRS flips a contractor on you. 

Think about the consequences of this for a second.

(1)  You were supposed to withhold federal income tax.

(2)  You were supposed to withhold social security.

(3)  You were supposed to match the social security.

(4)  You were supposed to remit those withholdings and your match to the IRS on a timely basis.

(5)  You were supposed to file quarterly employment reports accounting for the above.

(6)  You were supposed to issue W-2s to the employee at year-end.

(7)  You were supposed to send a copy of the W-2 to the Social Security Administration at year-end.

(8)  Payroll has some of the nastiest penalties in the tax Code.

This could be a business-shuttering event. I had a client several years ago who was faced with this scenario. The situation was complicated by fact that the IRS considered one of the owners to be a tax protestor. I personally did not think the owner merited protestor status, as he was not filing nonsense appeals with the IRS or filing delaying motions with the Tax Court. He was more …  not filing tax returns.  Nonetheless, I can vouch that the IRS was not humored.

Back to relief 2. Take a look at this bad boy:

§ 3509 Determination of employer's liability for certain employment taxes.

(a)  In general.

If any employer fails to deduct and withhold any tax under chapter 24 or subchapter A of chapter 21 with respect to any employee by reason of treating such employee as not being an employee for purposes of such chapter or subchapter, the amount of the employer's liability for-

(1)  Withholding taxes.

Tax under chapter 24 for such year with respect to such employee shall be determined as if the amount required to be deducted and withheld were equal to 1.5 percent of the wages (as defined in section 3401 ) paid to such employee.

(2)  Employee social security tax.

Taxes under subchapter A of chapter 21 with respect to such employee shall be determined as if the taxes imposed under such subchapter were 20 percent of the amount imposed under such subchapter without regard to this subparagraph .

Yes, you still owe federal income and social security, but it is a fraction of what it might have been. For example, you should have withheld 7.65% from the employee for social security. Section 3509(a)(2) gives you a break: the IRS will accept 20% of 7.65%, or 1.53%.

Is it great?

Well, no.

Might it be the difference between staying in business and closing your doors?

Well, yes.

Fewer Like-Kind Exchanges in 2018

The new tax bill changed like-kind exchanges.

This is Section 1031, which was and is a tax provision that allows one to defer taxes on a property sale - if one follows the rules.

I suspect that almost every practicing tax accountant has met with a client who said the following:

·      I sold property last year,

·      I hear that there is a tax break if I buy another piece of property

Well, yes there MIGHT be a tax break, but you have to follow the rules from the beginning, not just months later when you meet with your accountant.

The normal sequence is to sell the property first. It doesn’t have to be that way – you can start with the buy – but that is unusual. The tax nerds refer to that as a “reverse.”

There are ropes:

(1)  You want the money held by a third party, such as an attorney or title company;

(2)  You have to identify the replacement property within 45 days (there is some latitude in identifying replacement properties); and

(3)  You have to complete the whole transaction – sell and buy – within 180 days.

(4) Anticipate that you will be buying-up: buy more than what you sold.

(5)  Debt is tricky. To be safe, increase your debt, at least a little bit.  

(6)  You never want to receive cash from the deal. Cash is income – period.

If you wait to until you meet with your accountant, then you have probably blown requirement (1).

The most common like-kind that I see – I kid you not – is vehicle trade-ins. They happen every day, to the point that we do not even pay them attention. In the tax world, however, trade-ins are like-kind exchanges.

The next most common are real estate exchanges. I have probably seen at least one a year for the last couple of decades. Those usually go through a title company or attorney, and I have the pleasure of looking over a binder of paperwork that would weigh down a Clydesdale.

There are others. One can like-kind exchange personal property, for example. The rules are stricter than the rules for real estate, and for the most part I have not seen a lot of those.

The new tax bill made a big change to like-kind exchanges.

How?

Because personal property no longer qualifies for like-kind treatment.

So much for trade-ins.

But there is another kind that I thought of recently.

Think sports.

Yep, back in 1966 the IRS considered player contracts – if done correctly – to be property qualifying for like-kind.

I am unsure how professional sports will work-around this change. It is not an area I practice, although I would have loved to.

Why did Congress mess with this?

It wasn’t about player contracts. It rather had to do with art and collectibles. It had become de rigueur to like-kind exchange in the art world, as buyers had come to view art as just another tradable commodity. Think stocks, but with the option of delaying taxes until the end of time. This reached the attention of the Obama administration, which began the push to eliminate them.

It took another White House, but it finally got done.

Romancing The Income

Let’s discuss Blagaich, an early 2016 decision from the Tax Court. This is a procedural decision within a larger case of whether cash and property transfers represent income. 

Blagaich was the girlfriend and in 2010 was 54 years old.

Burns was the boyfriend and in 2010 was 72 years old.

Their romance lasted from November 2009 until March 2011.

It appears that Burns was fairly well heeled, as he wired her $200,000, bought her a Corvette and wrote her several checks. These added up to $343,819.

He was sweet on her, and she on him. Neither wanted to marry, but Burns wanted some level of commitment. What to do …?

On November 29, 2010 they decided to enter into a written agreement. This would formalize their “respect, appreciation and affection for each other.” They would “respect each other and … continue to spend time with each other consistent with their past practice.” Both would “be faithful to each other and … refrain from engaging in intimate or other romantic relations with any other individual.”

The agreement required Burns to immediately pay Blagaich $400,000, because nothing says love like a check you can immediately take to the bank.

Surprisingly, the relationship went downhill soon after entering into the agreement.

On March 10, 2011 Blagaich moved out of Burn’s house.

The next day Burns sent her a notice of termination of the agreement.

That same month Burns also sued her for nullification of the agreement, as she had been involved with another man throughout the entire relationship. He wanted his Corvette, his diamond ring - all of it - returned.

Somewhere in here Burns must have met with his accountant, as he/she sent Blagaich a Form 1099-MISC for $743,819.

She did not report this amount as income. The IRS of course wanted to know why.

The IRS learned that she was being sued, so they decided to hold up until the Circuit Court heard the case.

The Circuit Court decided that:

·        The Corvette, ring and cash totaling $343,819 were gifts from him to her.

·        The $400,000 was different. She was paid that under a contract. Flubbing the contract, she now had to pay it back.

Burns had passed away by this time, but his estate sent Blagaich a revised Form 1099-MISC for $400,000.

With the Circuit Court case decided, the IRS moved in. They increased her income by $743,819, assessed taxes and a crate-load of penalties. She strongly disagreed, and the two are presently in Tax Court. Blagaich moved for summary adjudication, meaning she wanted the Tax Court to decide her way without going through a full trial.

QUESTION: Do you think she has income and, if so, in what amount?

Let’s begin with the $400,000.

The Circuit Court had decided that $400,000 was not a gift. It was paid pursuant to a contract for the performance of services, and the performance of services usually means income. Additionally, since the payment was set by contract and she violated the contract terms, she had to repay the $400,000.

She argued that she could not have income when she had to pay it back. In legal-speak, this is called “rescission.”

In the tax arena, rescission runs head-on into the “claim of right” doctrine. A claim of right means that you have income when you receive an increase in wealth without a corresponding obligation to repay or a restriction on your being able to spend. If it turns out later that you in fact have to repay, then tax law will allow you a deduction – but at that later date.

Within the claim of right doctrine there is a narrow exception IF you pay the money back by the end of the same year or enter into a binding contract by the end of the same year to repay. In that case you are allowed to exclude the income altogether.

Blagaich did not do this. She clearly did not pay the $400,000 back in the same year. She also did not enter in an agreement in 2010 to pay it back. In fact, she had no intention to pay it back until the Circuit Court told her to.

She did not meet that small exception to the claim-of-right doctrine. She had income. She will also have a deduction upon repayment.

OBSERVATION: This is a problem if one’s future income goes down. Say that she returns to a $40,000/year job. Sure, she can deduct $400,000, but she can only offset $40,000 of income and the taxes thereon. The balance is wasted. Practitioners sometimes see this result with athletes who retire, leaving their sport (and its outsized paychecks) behind. It may never be possible to get back all the taxes one paid in the earlier year.

Let’s go to the $343,819.

She argued that the Circuit Court already decided that the $343,819 was a gift. To go through this again is to relitigate – that is, a double jeopardy to her. In legal-speak this is called “collateral estoppel.”

The Court clarified that collateral estoppel precludes the same parties from relitigating issues previously decided in a court of competent jurisdiction.

It also pointed out that the IRS was not party to the Circuit Court case. The IRS is not relitigating. The IRS never litigated in the first place.

She argued that the IRS knew of the case, requested and received updates, pleadings and discovery documents. The IRS even held up the tax examination until the Circuit Court case was decided.

But that does not mean that the IRS was party to the case. The IRS was an observer, not a litigant. Collateral estoppel applies to the litigants. That said, collateral estoppel did not apply to the IRS.

Blagaich lost her request for summary, meaning that the case will now be heard by the Tax Court.

What does this tax guy think?

She has very much lost the argument on the $400,000. Most likely she will have to pay tax for 2010 and then take a deduction later when she repays the money. The problem – as we pointed out – is that unless she has at least $400,000 in income for that later year, she will never get back as much tax as she is going to pay for 2010. It is a flaw in the tax law, but that flaw has been there a long time.

On the other hand, she has a very good argument with the $343,819. The Court was correct that a technical issue disallowed it from granting summary. That does not however mean that the technical issue will carry the day in full trial. That Circuit Court decision will carry a great deal of evidentiary weight.

We will know the final answer when Blagaich v Commissioner goes to full trial.