Can a Tunnel Bridge Agent be a Professional Gambler, Too?

The Tax Court looked at whether someone who worked full time as a Tunnel Bridge Agent could also be a professional gambler. There is a lot in the decision, including some things that I believe the Court gets wrong.

The opinion first describes the differences between being a professional gambler and an amateur gambler. If you are unaware of the differences in the tax treatment, this opinion is must-reading. Unfortunately, the opinion gets the definition of a professional gambler only half-right. “To be a professional gambler, the taxpayer must engage in gambling for profit,” is what the opinion states (citing Commissioner v. Groetzinger, 480 U.S. 23, 35 (1987)). But the courts have held that you need to be gambling for your livelihood, a stricter standard. There are numerous amateur gamblers who do so for a profit (I am one of those), but I’m an amateur gambler. My livelihood comes from my tax practice, but I’m skilled (or lucky) enough to make money from poker.

In any case, today’s taxpayer, Mr. B, doesn’t even pass this test. His first problem is where he gambled and his recordkepping or, should I say, his lack of recordskeeping.

Boneparte gambled at horse racetracks and in casinos. At the casinos his preferred game was baccarat, but he also played other table games as well as slots. Sometimes he gambled alone, and sometimes he gambled with a friend. He gambled primarily in Atlantic City. He did not keep a contemporaneous written log of winnings and wagers.

If you’re in business, you are supposed to keep records. The IRS rules on gambling—and these date back to the 1970s—mandate a contemporaneous, written log. (Remember, those rules were written well before smartphones or any cellphone. Today, computer records would most likely be accepted.) But if you have no records, you’re going to have trouble substantiating that you’re a professional gambler. Yes, Mr. B had casino win-loss statements but (a) these are not guaranteed to be accurate (a point the Court missed in its opinion), and (b) professionals want to know what they’re succeeding in and failing in; the only way to do that is to keep your own records.

As an aside, it’s hard to be a professional gambler when you are playing games of pure chance with a house (casino) advantage. That’s why most professional gamblers play poker (where you’re playing against other players); a lesser number of professional gamblers partake in sports betting and “advantage” video poker (where there’s a small player advantage with perfect play). But I digress…

The Court then looked at the nine-factor test of whether an activity is engaged in for profit.

(1) [T]he manner in which the taxpayer carries on the activity; (2) the expertise of the taxpayer or his advisers; (3) the time and effort expended by the taxpayer in carrying on the activity; (4) the expectation that assets used in the activity may appreciate in value; (5) the success of the taxpayer in carrying on other similar or dissimilar activities; (6) the taxpayer’s history of income or losses with respect to the activity; (7) the amount of occasional profits, if any, which are earned; (8) the financial status of the taxpayer; and (9) elements of personal pleasure or recreation.

Mr. B. didn’t lose on all of the factors: Factor #4 (expectation of asset appreciation) was held not to apply. With the Court ruling that Mr. B. Isn’t a professional gambler, most of the rest of the opinion goes into calculation issues of his return and penalty calculations.

However, I want to point out an error the IRS made that I’ve seen in my practice. If a casino win-loss statement shows a net loss $14,887, and we know that the gambler had gross wins (before losses) of $18,000, his gross losses must be $32,887. That’s simple math. I once had to explain to an IRS Revenue Agent how this works; it took about a half-hour for him to grasp the concept. In this case, the IRS was holding this same idea that Mr. B’s gross loss was his total loss. The Court, though, understood basic math:

As explained above, two propositions are true: (1) the gains from wagering transactions for which there was gain total $18,000, and (2) the gains from wagering transactions for which there was a gain minus the losses from wagering transactions for which there was a loss equal -$14,887. It mathematically follows from these two propositions that the losses from wagering transactions for which there is a loss equal -$32,887 (i.e., $18,000 ! $32,887 = -$14,887). [Mr. B] is entitled to a section 165(d) deduction equal to this amount to the extent of gains from wagering transactions. This gain is $18,000. Therefore his section 165(d) deduction is $18,000.

Mr. B’s returns were self-prepared. He included his gambling on both a Schedule C and as Other Income. In almost all cases, you’re either a professional gambler or an amateur gambler (not both). The IRS assessed both the late filing penalty (Mr. B’s return was postmarked after the April deadline) and the accuracy-related penalty; both were sustained.

Mr. B gives a good example of someone who wanted to be a professional gambler because it would help him save on his taxes. Unfortunately for him, he neither treated his business professionally nor was he able to show the Tax Court that he was a professional gambler.

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It’s One 1099 Per Person, Or the Most Stupid and Hilarious Thing I’ve Seen in Some Time

One of my clients, Barri Brown (all names in this post are fictitious), was missing a 1099 issued by one of the two large Daily Fantasy Sports (DFS) companies. It didn’t show on her Wage & Income Transcript, so she called their accounting department and requested a copy. A few days later they emailed it to her. She forwarded it on to me and I entered it into her return.

And then I took a look at the pdf and saw that it was 18 pages long. I wondered what kind of attachments this company would send on a 1099? Perhaps a breakout of state tax issues (although that didn’t apply to my client). Or perhaps some internal accounting records detailing Ms. Brown’s profits and losses.

How about the 1099s for everyone this company serviced with the last name of Brown? The second page is that of Brett Brown, the third page is Daniel Brown, etc. At least only the last four digits of the social security numbers were shown (but both my client and I know the exact amount of Brett Brown’s DFS income from this site in 2016).

In one way, this is hilarious. Apparently it was easier for that clerk to email the 1099s for all the Browns to my client than to just send the specific 1099. (I have to wonder about how they create their 1099s, but that’s a question for another day.)

In another way, it’s stupid. Hasn’t this company heard of privacy concerns and laws? My client has every right to know her income, but absolutely no right to know Brett Brown’s income (unless Mr. Brown elects to tell one of us).

But my client asked a very good question. “That is HILARIOUS and absurd and maybe illegal?” I’m not an attorney, so I can’t state with certainty whether this was a violation of the law. The reality is that this was almost certainly a stupid error, and there wasn’t the intent to do something illegal.

(Tax professionals fall under the provisions of the Federal Trade Commission Act. If a tax professional were to deliberately do this, it definitely could be a violation of the FTC Act.)

Unfortunately, the data breach at Equifax and this act of stupidity reinforce my belief that businesses need reminders to treat data security very seriously. My client used an Employer Identification Number (EIN) with the DFS company; I strongly recommend that sole proprietors (like my client) do that whenever possible. A stolen EIN (for a sole proprietor) can’t be used to file a personal tax return.

Let me give a helpful hint to those issuing 1099s and sending them out: It’s one to a customer. Barri Brown doesn’t need Steven Brown’s 1099. Luckily for this company, my client is able to laugh this off (as am I). The problem is that if this happened to Ms. Brown, it likely happened to Mr. Nelson and others.

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IRS Suspends ASFR Program

Via Procedurally Taxing comes news that the IRS has suspended the Automated Substitute for Return (ASFR) program. This doesn’t sound like much, but this is huge news.

First, for those who aren’t tax geeks, the ASFR program is an automated program to prepare substitutes for tax returns if you don’t file one. Let’s say you have five 2016 1099-MISC’s received totaling $100,000. You foolishly decide not to file a tax return. The IRS will prepare a return for you, making assumptions about your marital status (you’re single) and your business and itemized deductions (none). The IRS then sends you a copy of the return demanding money, adding in penalties (late filing, late payment) and interest. Many people who get ASFRs file tax returns to replace the ASFR; others write the IRS. All of these have to be reviewed by humans. Others simply ignore the IRS and then get a notice of deficiency (which can be appealed to Tax Court).

Presumably the IRS has concluded that the money raised by the ASFR program has not offset the costs of the program. That’s the conclusion of Carl Smith on Procedurally Taxing and my conclusion, too.

Does this mean that you don’t have to file tax returns? Definitely not. If you don’t and the IRS catches you, you will still be subject to all the possible penalties; additionally, non-filing of tax returns is a crime.

As a tax professional, I’m not a fan of the suspension. Sure, this program may have been overall a cost center; however, it likely forced noncompliant individuals in to compliance—and that’s the goal of the IRS (current compliance). Overall, this change seems to me to be a shocking mistake.

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Prepare to Panic!

Today is Monday, September 25, 2017. Exactly three weeks from today is Monday, October 16, 2017. That’s the deadline for individual taxpayers on extension to file their tax returns (save for those in hurricane disaster zones in Florida, Georgia, Texas, Puerto Rico, and the Virgin Islands). If you have yet to send your paperwork to your tax professional it’s past the time to do so. Yes, it’s time to panic.

If your return is simple and straightforward, stop procrastinating and get it done and filed. If your return has any sort of complexities, you must start working on it now! Your tax professional needs time to get it done correctly. You need to turn in that paperwork post haste. If you’ve procrastinated, stop, sit down, and get it done.

It may already be too late for your return to be timely filed with many tax professionals. For example, our official deadline was last Wednesday. Luckily, we’re not behind so our procrastinating clients are still in good shape. However, that might not be the case with all tax professionals. And I can guarantee if you drop off your paperwork with us on October 13th your return is almost certainly not going to be timely filed.

If you file late, it’s as if you never filed your extension. So sit down and get everything done now! Of course, if you like paying a 25% penalty, simply procrastinate for another three weeks.

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The Train to Nowhere Remains a Boondoggle

California’s high speed rail, aka The Train to Nowhere, remains likely to never carry passengers between Northern California and Southern California. Perhaps the segment linking Merced and Shafter (just north of Bakersfield) will run (although unlikely at high speed); more likely, it will never run. So the image that comes into my mind is the following:

via GIPHY

There have been some developments since I last reported on the train. First, the California Supreme Court ruled at the end of July that California law was not preempted by federal law and that a number of environmental suits against the high speed rail authority could continue.

Meanwhile, Quentin Kopp, the man who introduced the rail line, now calls the line foolish. In an interview with reason.com he said,

It is foolish, and it is almost a crime to sell bonds and encumber the taxpayers of California at a time when this is no longer high-speed rail. And the litigation, which is pending, will result, I am confident, in the termination of the High-Speed Rail Authority’s deceiving plan…

[The selling of bonds is] deceit. That’s not a milestone, it’s desperation, because High-Speed Rail Authority is out of money.

Ouch. Baruch Feuigenbaum, assistant director of transportation policy for the Reason Foundation, stated, “The costs of building [high-speed rail] projects usually vastly outweigh the benefits…Rail is more of a nineteenth century technology [and] we don’t have to go through these headaches and cost overruns to build a future transportation system.”

Look on the bright side Californians, the project will likely need subsidies from the state of only $100 million a year. That’s not bad, right?

Or better, I’m sure the 10 Shafterites looking to head to Merced each day will love the train (as will the 20 residents of Merced looking to head to Shafter each day).

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Harvey and Irma Relief Includes the FBAR

Taxpayers with $10,000 aggregate in one or more foreign financial accounts must file an FBAR (Report of Foreign Bank and Financial Accounts, Form 114) with the Financial Crimes Enforcement Network (FINCEN). FINCEN has announced on their website that they are following the IRS’s lead and extending the due date for account holders impacted by Hurricanes Harvey and Irma until January 31, 2018.

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IRS Transcript Delivery System Failing for Many Users; No Fix Time

One of the major tools I use is the IRS’s e-Services system; the component I use the most is the Transcript Delivery System (TDS). Last weekend, the IRS did a major “upgrade” of the system. I have to put upgrade in quotes because it’s been a downgrade for me and many other users. The system does not recognize that I have authority (a Power of Attorney or a Tax Information Authorization) on file.

The problem appears to be that the IRS must also migrate their Centralized Authorization File (CAF) database. This database is how the IRS keeps track of which returns (names, social security numbers, and tax years) tax professionals are authorized for. Unfortunately, the migration of this database hasn’t gone smoothly.

Until this is resolved tax professionals will need to call the IRS’s Practitioner Priority Service and request the IRS fax over any transcripts that are needed. I just had to do this and was on hold for only 11 minutes so it could be much worse.

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IRS Gives Tax Deadline Relief to Victims of Hurricane Irma

The IRS today announce that they are extending tax filing deadlines for victims of Hurricane Irma to January 31, 2018. The relief applies to any area designated by FEMA as qualifying for individual assistance (areas in Florida, Puerto Rico, and the Virgin Islands currently). Here is the pertinent part of the IRS announcement:

The tax relief postpones various tax filing and payment deadlines that occurred starting on Sept. 4, 2017 in Florida and Sept. 5, 2017 in Puerto Rico and the Virgin Islands. As a result, affected individuals and businesses will have until Jan. 31, 2018, to file returns and pay any taxes that were originally due during this period.

This includes the Sept. 15, 2017 and Jan. 16, 2018 deadlines for making quarterly estimated tax payments. For individual tax filers, it also includes 2016 income tax returns that received a tax-filing extension until Oct. 16, 2017. The IRS noted, however, that because tax payments related to these 2016 returns were originally due on April 18, 2017, those payments are not eligible for this relief.

A variety of business tax deadlines are also affected including the Oct. 31 deadline for quarterly payroll and excise tax returns. Businesses with extensions also have the additional time including, among others, calendar-year partnerships whose 2016 extensions run out on Sept. 15, 2017 and calendar-year tax-exempt organizations whose 2016 extensions run out on Nov. 15, 2017. The disaster relief page has details on other returns, payments and tax-related actions qualifying for the additional time.

In addition, the IRS is waiving late-deposit penalties for federal payroll and excise tax deposits normally due during the first 15 days of the disaster period. Check out the disaster relief page for the time periods that apply to each jurisdiction.

The IRS automatically provides filing and penalty relief to any taxpayer with an IRS address of record located in the disaster area. Thus, taxpayers need not contact the IRS to get this relief. However, if an affected taxpayer receives a late filing or late payment penalty notice from the IRS that has an original or extended filing, payment or deposit due date falling within the postponement period, the taxpayer should call the number on the notice to have the penalty abated.

In addition, the IRS will work with any taxpayer who lives outside the disaster area but whose records necessary to meet a deadline occurring during the postponement period are located in the affected area. Taxpayers qualifying for relief who live outside the disaster area need to contact the IRS at 866-562-5227. This also includes workers assisting the relief activities who are affiliated with a recognized government or philanthropic organization.

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IRS Appeals Steele Decision

Earlier this year a court ruled that the IRS cannot charge for Practitioner Tax Identification Numbers (PTINs). To no one’s surprise, yesterday the IRS appealed the decision to the US Court of Appeals for the District of Columbia. It will likely be sometime next year before the case is heard and a decision rendered. I also expect the IRS to ask the Court of Appeals to lift the permanent injunction on charging for PTINs while the appeal is being heard.

I will update when there is additional news.

Hat Tip: NAEA

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Can You Use a §1031 Exchange to Defer Gain with Cryptocurrency?

I recently wrote an article noting that if you exchange one cryptocurrency for another you have a capital gain (or loss). I was recently asked if you could defer such a gain by using a §1031 Exchange.

What Is a §1031 Exchange? A §1031 exchange is a way of deferring the capital gain on a property by exchanging it for another property. And didn’t the IRS rule that cyrptocurrency is property? So let’s look at the statutory language of §1031:

26 U.S. Code §1031 – Exchange of Property Held for Productive Use or Investment
(a) Nonrecognition of Gain or Loss from Exchanges Solely In Kind
(1) In General No gain or loss shall be recognized on the exchange of property held for productive use in a trade or business or for investment if such property is exchanged solely for property of like kind which is to be held either for productive use in a trade or business or for investment.

Well, there’s the first two hurdles: Is cyrptocurrency held for productive use in a trade or business or for investment? Well, cryptocurrency likely isn’t held for productive use in a trade or business but it certainly is held by some for investment.

But that wasn’t all of 26 U.S. Code §1031. There is property that is not eligible for like-kind treatment. Let’s now look at §26 USC 1031(a)(2):

(2) Exception This subsection shall not apply to any exchange of—
(A) stock in trade or other proprety held primarily for sale,
(B) stocks, bonds, or notes,
(C) other securities or evidences of indebtedness or interest,
(D) interest in a partnership,
(E) certificates of trust or beneficial interests, or
(F) choses in action.

There’s a problem here: The closest analog to how cyrptocurrency should be treated are stocks and bonds. And §26 USC (a)(2)(B) states that you can’t do a §1031 exchange for stocks and bonds.

“But Russ,” you say, “cyrptocurrency isn’t stocks or bonds. It’s a virtual currency. So if I exchange Bitcoin for Ethereum, that should be ok, right?” Let’s assume that §26 USC (a)(2)(B) doesn’t apply. Are Bitcoin and Ethereum like-kind property?

Unfortunately, the answer is a maybe, with “no” more likely than “yes.” The IRS has been asked to look at exchanging gold bullion for gold coins, gold coins for other gold coins, and gold bullion for silver bullion as §1031 exchanges. You can use a §1031 exchange to exchange Mexican 50 peso gold coins for Austrian 100 corona gold coins and gold bullion for Canadian Maple Leaf gold coins. However, you cannot use a §1031 exchange to exchange gold bullion held for investment for silver bullion held for investment (different metals used in different ways), $20 gold numismatic-type coins for South African Krugerrand bullion-type gold coins (different underlying investments and different valuation bases), and Swiss Francs for US Double Eagle Gold Coins (numismatic versus circulating currency).

I believe the IRS would likely rule that Bitcoin and Ethereum are two different underlying investments and do not qualify for like-kind treatment.

But let’s further assume I’m wrong, and they do qualify. You go on a Bitcoin exchange and swap n Bitcoins for x Ethereum. Is that a §1031 Exchange?

Well, there are numerous technical rules regarding a §1031 exchange. First, they must be reported on IRS Form 8824 so the idea of simply ignoring them on your tax return is a certain way to make sure your transaction is not a §1031 exchange. There are 67 pages of regulations on §1031 exchanges (search for “1031” in the link for them). Most §1031 exchanges use a Qualified Intermediary. Certainly the dealer I use is that Qualified Intermediary, right?

Well, almost certainly not. When you use an Exchange to buy a cryptocurrency, the dealer almost certainly doesn’t meet the technical requirements listed in the regulations. There is no paperwork; the trades occur close to instantly (not over the months it takes to complete a §1031 exchange); and several other issues with a dealer.

“But Russ,” you say, “my friend Scott has x Ethereum and is willing to swap it for my n Bitcoins. We agree to directly swap our positions. That would be a §1031 exchange, right?”

This is the most likely to meet IRS scrutiny, but only if the IRS considers Bitcoin and Ethereum to be like-kind. The tax professional community has asked the IRS to give guidance on this, but the IRS (to date) has ignored this issue. You could request a Private Letter Ruling from the IRS. A Private Letter Ruling is a means to get an answer from the IRS given a specific set of facts. The Private Letter Ruling binds the requestor and the IRS. However, you must pay for a Private Letter Ruling; the cost will be at least $2,400. It also takes time to receive the Private Letter Ruling (think months, not weeks).


The conclusion I’ve drawn is that most exchanges of one cryptocurrency for another do not qualify as §1031 exchanges and it’s more likely than not that the IRS will rule that two different cryptocurrencies are not eligible for like-kind treatment.

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