Archive for the ‘Gambling’ Category

Update on the Future of Daily Fantasy Sports

Thursday, November 19th, 2015

So far, I’ve been accurate on my predictions. Back in February 2014 I wrote,

Unfortunately, many states look at just an element of chance to determine if something is gambling. And there’s no doubt that daily fantasy sports have such an element. The problem is that these sites are starting to bring in large dollars. That attracts attention, and some state attorney general is going to wonder the same thing that I am. He or she will conclude that the Duck Test applies and that these are gambling sites in violation of his or her state’s laws. [emphasis in original]

Last month I wrote,

I expect DFS to follow two different paths in the majority of states. Some states will simply declare it as gambling, making it effectively illegal in those states. Other states will tacitly declare it as gambling but allow regulation of the activity. There will be a minority of states that allow DFS to continue as an unregulated activity. Where one month ago you could play DFS in 45 of the 50 states, that number is down to 42 to 44 states (depending on the DFS site). I expect that number to continue to fall.

Events have moved faster than I thought they would. The New York Attorney General declared DFS to be gambling, and has asked a court for an injunction. One of the two major sites, FanDuel, has stopped offering contests for New Yorkers. The hearing will be next Wednesday. The Massachusetts Attorney General has proposed regulations.

As for New York, I think FanDuel is operating far wiser than DraftKings. DraftKings is still allowing New York residents to play on the site. Given that there is a non-zero chance that the company will find it outself ordered to stop, and that operating in violation of state law would be a predicate offense for possible federal charges, I think DraftKings is making the wrong decision. (I will point out again that I am not an attorney, and nothing I’m writing should be construed as legal advice.) If you ask me the most likely result of the New York Attorney General’s action, it’s that the sites will find themselves enjoined from serving New York customers. This isn’t a certainty, but if you’re going to place a bet on the results that’s the favored side.

I still think we will end up with a dichotomy within the states. States that are notoriously anti-gambling or have constitutional provisions against gambling (including much of the South: Texas, Florida, and Tennessee; Utah, and Hawaii) will ban DFS, either by Attorney General rulings or by court actions. Other states will regulate DFS. Some states will order the DFS companies to shut down until regulations are in place. A very small number of states will just ignore the issue, and leave DFS in an unregulated state.

DFS proponents need to remember that a regulator’s first instinct when confronted with something new is to ban it. Add that to the fact that DFS is legal by way of a loophole (in the view of regulators) and you get a strong inclination for them to end DFS.

That’s the most likely outcome. However, there is still the chance that DFS could end completely. There are federal investigations of the sites which could, if indictments result, end the industry.

This is a fascinating story–and the greed of the sites has sped up the story line. It was inevitable that DFS would attract scrutiny. The pace of that scrutiny sped up because the sites went overboard in their advertising and had very poor visuals. We’ll all be able to see the future of this product unfold in the next few weeks.

The Real Winners of the World Series of Poker (2015 Edition)

Tuesday, November 10th, 2015

Nine individuals came to Las Vegas over the last three days to compete for the championship at the World Series of Poker (WSOP). Who would be the lucky winner? And who really got to keep the money?

Last year the winner was London, so to speak. Most of the participants hailed from the United Kingdom (well, resided there) to save on taxes. The United Kingdom does not tax gambling winnings and the US-UK Tax Treaty exempts gambling winnings from taxation. This year, only one of the participants escaped paying tax on his winnings; he is not from the UK.

It’s back to normal this year. As you will soon see, the big winner, almost doubling the amount of the after-tax winnings of the “winner,” was the Internal Revenue Service. The IRS collected $8,467,091 out of the $24,806,976 awarded at the final table (34.13%).

One other note: I do need to point out that many of the players in the tournament were “backed.” Poker tournaments have a high variance (luck factor). Thus, many tournament players sell portions of their action to investors to lower their risk. It is quite likely that most (if not all) of the winners were backed and will, in the end, only enjoy a portion of their winnings. I ignore backing in this analysis. Now, on to the winners.

Congratulations to Joe McKeehen of North Wales, Pennsylvania. The professional poker player dominated play at the final table. He came in with the chip lead and never relinquished it and never looked challenged. For finishing first out of 6,420 entrants (each of whom paid the $10,000 entry fee) he won $7,683,346. As a professional poker player, he’ll owe self-employment tax along with his federal income tax ($3,073,240), Pennsylvania state income tax ($235,879), and the local township (North Wales Boro) Earned Income Tax ($76,833), a total of $3,385,952 (44.07%). He’ll get to keep an estimated $4,297,394 of his winnings.

Finishing second was Joshua Beckley of Marlton, New Jersey. Mr. Beckley won $4,470,896 for his second place finish. His percentage tax burden is higher than the winners at 46.56%; that’s because New Jersey is decidedly not a low-tax state. Still, he’ll end up paying $2,081,719 in tax.

Neil Blumenfield of San Francisco finished in third place. In most years the 61-year old former technology executive would have been the oldest player at the final table. However, he was eclipsed this year by a 72-year old! Still, it makes me feel pretty good about my future poker prospects. Mr. Blumenfield was one of two amateurs at the table, so he’s not impacted by self-employment tax. However, he resides in California, so his tax burden is the largest of any of the Americans at 46.86%. I estimate he will keep just $1,805,764 of the $3,398,298 he won (losing $1,592,534 in tax).

In fourth place was Max Steinberg of Las Vegas. Mr. Steinberg, the only one of the nine individuals who had previously won a WSOP bracelet (for winning an event at the WSOP), is a professional Daily Fantasy Sports and poker player. He may be looking to relocate after Nevada effectively ended DFS within the Silver State. Of the individuals who owe income tax, Mr. Steinberg faces the lowest tax rate (40.99%). That’s because while he will owe federal income tax and self-employment tax (totaling $1,072,055 of the $2,615,361 he won), Nevada does not have a state income tax.

Ofer Zvi Stern of Herzliya, Israel, finished in fifth place. Mr. Stern works in the technology industry in Israel and is an amateur gambler. The US-Israel Tax Treaty does not cover gambling, so Mr. Stern loses 30% of his winnings $573,427 of $1,911,423) to the IRS. Gambling income is taxed in Israel. While Mr. Stern should get a tax credit for the tax he paid to the IRS, he’ll still owe an additional $326,679 to the Israel Tax Authority–a total tax bite of 47.09%.

Thomas Cannuli of Cape May, New Jersey, finished in sixth place. Mr. Cannuli is a professional gambler, so he owes income tax to the IRS and New Jersey and self-employment tax. While he won $1,426,283 for finishing sixth, after taxes of $640,287 (44.89%) he’ll only get to keep $785,996.

Pierre Neuville, a retired businessman from Knokke-Heist, Belgium, finished seventh. Mr. Neuville was the oldest November Nine participant (he’s 72) ever. While he finished in seventh place by pre-tax winnings, Mr. Neuville finished in fifth place by after-tax winnings. The US-Belgium Tax Treaty exempts gambling winnings from US taxation, so Mr. Neuville owes nothing to the IRS. Belgium doesn’t tax gambling winnings of amateur gamblers, so he owes nothing to Belgium. That will likely soften the blow of being the third person eliminated at the final table.

The eighth place finisher was Federico Butteroni of Rome, Italy. Mr. Butteroni only played two hands at the final table, and his second hand ended his tournament. While he won $1,097,056, he’ll only get to keep $571,566 (a tax bite of 47.90%). The US-Italy Tax Treaty exempts gambling winnings from US taxation, so none of his winnings were withheld for the IRS. However, Italy does tax gambling winnings from non-European Union countries. (There is current litigation regarding taxes owed for winnings within the E.U., but it appears that, for the present, such winnings are not subject to taxation.) The tax appears to be a flat 47.90%. Mr. Butteroni faces the highest tax bite by percentage of any of the final table participants.

Patrick Chan of Brooklyn, New York was knocked out on the second hand of the final table. Unfortunately for Mr. Chan, he did not add anything to the $1,001,020 he took home in July. He only gets to keep an estimated $545,614 of his winnings (45.49%) because he owes federal income tax, self-employment tax (he is a professional poker player), state income tax, and New York City income tax.

Here’s a table summarizing the tax bite:

Amount won at Final Table $24,806,976
Tax to IRS $8,467,091
Tax to Agenzia delle Entrate (Italy) $525,490
Tax to New Jersey Division of Taxation $493,422
Tax to Franchise Tax Board (California) $425,550
Tax To Israel Tax Authority $326,679
Tax to Pennsylvania Department of Revenue $235,879
Tax to New York Dept of Taxation & Finance $102,605
Tax to North Wales Boro $76,833
Total Tax $10,080,122

That’s a total tax bite of 42.95%.

Here’s a second table with the winners sorted by their estimated take-home winnings:

Winner Before-Tax Prize After-Tax Prize
1. Joe McKeehen $7,683,346 $4,297,394
2. Joshua Beckley $4,470,896 $2,389,177
3. Neil Blumenfield $3,398,298 $1,805,764
4. Max Steinberg $2,615,361 $1,543,306
7. Pierre Neuville $1,203,293 $1,203,293
5. Ofer Zvi Stern $1,911,423 $1,011,317
6. Thomas Cannuli $1,426,283 $785,996
8. Federico Butteroni $1,097,056 $571,566
9. Patrick Chan $1,001,020 $545,614
Totals $24,806,976 $14,153,427

While Pierre Neuville finished in seventh place, he ended up in fifth place based on his after-tax income. Unlike all of the other winners, Mr. Neuville gets to keep all of his winnings. It’s always nice when your after-tax income equals your before-tax income.

Last year, the IRS didn’t finish in first place. This year, the IRS was back in its normal spot: first place. The $8,467,091 it will receive exceeds the first place prize of $7,683,346 by 10%. As I noted before, it’s just less than double the after-tax winnings of the actual winner. That’s because we all know that the house (the IRS) always wins.

DFS Gets the Boot in New York

Tuesday, November 10th, 2015

New York State’s Attorney General, Eric Schneiderman, sent a letter to DraftKings and Fan Duel ordering them to cease offering their Daily Fantasy Sports (DFS) wagers games to New Yorkers. According to both ABC and ESPN, Attorney General Schneiderman sent a letter to both companies calling contest entries “wagers.”

“Our review concludes that DraftKings’/FanDuel’s operations constitute illegal gambling under New York law,” Schneiderman wrote in the letter, obtained by ESPN’s David Purdum and Darren Rovell, and ABC News.

The two sites are apparently going to fight this action.

“Fantasy sports is a game of skill and legal under New York State law,” FanDuel said in a statement. “This is a politician telling hundreds of thousands of New Yorkers they are not allowed to play a game they love and share with friends, family, coworkers and players across the country. The game has been played — legally — in New York for years and years, but after the Attorney General realized he could now get himself some press coverage, he decided a game that has been around for a long, long time is suddenly now not legal.”

DraftKings said they will look at legal options. (UPDATE: After I first posted this, there is a report that DraftKings will fight this.)

Let me state something that should be obvious to anyone who partakes in DFS: It’s gambling. Sure, it’s skillful gambling, but as I wrote in February 2014 it meets the criteria of what gambling is. And it is quite likely that FanDuel will be proven wrong under New York law.

The problem is that New York and many other states look at whether there’s an element of chance. Sure, skill predominates but there’s no way to honestly state there’s not an element of chance in DFS.

New York is definitely not going to be the last state where DFS gets the boot. I suspect Florida (where an Attorney General opinion makes legal DFS dubious at best) and Texas (where the politicians think gambling is a huge sin) are additional states in deep trouble.

What should DFS players do if they want to continue enjoying DFS? You should call your state representatives now. State legislators do listen to the public. And state legislators can absolutely influence what other elected politicians (e.g. state Attorney Generals) do.

Additionally, DFS players should consider keeping only the amount of money they need on the sites. The New York Attorney General statement used the words “criminal activity” to describe DFS. While I am hopeful that the DFS sites use segregated trust accounts, neither DraftKings nor FanDuel has confirmed that they do. It’s better safe than sorry, and that’s a good course of action today. (UPDATE: With the news that DraftKings will (apparently) fight this action, I now strongly advise that individuals keep just the minimum amount necessary on each site. I suspect that criminal charges are in the near future, and seizure of bank accounts is now a real possibility. The New York Attorney General will look at DraftKings’ continuing to operate in New York State as a slap in the face.)

DFS is in deep trouble, and the most likely outcome is a regime very similar to the current state of online poker in the United States–four to six states where DFS is legal. This doesn’t have to be how it winds up, but the arrogance of how the companies have been perceived to act (and are continuing to act) along with how gambling is traditionally regulated in the US makes that the most probable result.

UPDATE #2: Here is a link to a New York Times article that includes the letters to FanDuel and DraftKings. (Link to FanDuel letter; link to DraftKings letter. Note that the letters have basically identical content.) These letters warn that if the two sites do not cease operations, they will be subject to prosecution under various New York statutes. If these sites continue to operate in the face of the New York Attorney General notice, things are likely to get very ugly very fast.

Time Running Out on the Miccosukee Tribe’s Battle with the IRS

Wednesday, November 4th, 2015

I have sympathy when taxpayers battle the IRS over legitimate issues. Indeed, I’m all for fighting the IRS when they’re (imho) wrong. However, fighting quixotic battles when you are wrong isn’t a good idea. The Miccosukee Tribe in Florida is in that position.

The Miccosukees operate a successful casino near Miami. The tribe itself is exempt from taxation (it’s a sovereign nation). However, the members of the tribe are not exempt from taxation when they receive income related to the casino. And therein lies the issue.

Beginning in 2012 (or perhaps even earlier) the IRS was wondering why payments to tribe members weren’t being reported (on information reporting forms) and taxes withheld. The IRS sent requests to the tribe, and eventually summonsed material from the tribe and the tribe’s financial institutions. The tribe fought the summonses claiming sovereign immunity. The tribe lost the battles, most recently with this decision in June. (It’s unclear if the tribe has since provided this information to the IRS.)

Meanwhile, approximately 20 tribe members were sent Notices of Deficiency by the IRS pertaining to distributions from 2000-2005. The tribe members filed Tax Court petitions in 2013. As best as I can tell, no case related to this has yet been decided.

Separately, the IRS issued tax, penalties and interest on the non-withholding withholding (that is, the money that the IRS thinks should have been withheld by the Miccosukee tribe). The IRS issued a lien and levy notice. The Miccosukee Tribe had a Collection Due Process hearing. When asked to provided financial information the tribe refused. The tribe lost the Collection Due Process Hearing and then filed a Tax Court petition.

The tribe disputed both the underlying liability and the collection activity (the latter, as an abuse of discretion). In May 2014 the Tax Court used an order for summary judgment against the Miccosukee tribe on the underlying liability. Because the tribe had an opportunity to dispute the underlying liability at Appeals, the Court ruled that the tribe could not dispute it in the Tax Court case.

The Tax Court held a trial in March, and ruled today that the levy was not an abuse of discretion.

It is clear from our review of the record that the SO [settlement officer] verified that the requirements of applicable law and administrative procedure were followed and that in sustaining the filing of the NFTLs and the proposed levy the SO properly balanced “the need for the efficient collection of taxes with the legitimate concern of * * * [petitioner] that any collection action be no more intrusive than necessary.” Petitioner did not raise any valid challenge to the appropriateness of the NFTL filings and the proposed levy. Furthermore, petitioner did not submit the financial information necessary for the SO to consider an installment agreement. There is no abuse of discretion when a settlement officer declines to consider collection alternatives under these circumstances…see also sec. 301.6330-1(e)(1), Proced. & Admin. Regs. (“Taxpayers will be expected to provide all relevant information requested by Appeals, including financial statements, for its consideration of the facts and issues involved in the hearing.”). Therefore, we hold that the SO’s determination to sustain the filing of the NFTLs and proceed with the proposed levy was not an abuse of discretion. [citations omitted]

While I expect the Miccouskee Tribe to file an appeal, and this will delay any IRS action for the time while an appeal is pending, it’s clear that time is running out for the Miccosukee Tribe on this matter. They may not want to provide their financial information to the IRS, but they have to. They also need to start complying with the law in regards to reporting and withholding casino income payments. Years ago, the US government ended up owning part of the Bicycle Casino. It wouldn’t surprise me that at some date in the near future that the Miccosukee’s casino is under new management.

The Wagering Excise Tax and DFS

Tuesday, October 20th, 2015

I’m focusing on the tax aspects of daily fantasy sports (DFS) this week. It’s beneficial for DFS participants for the activity to be considered gambling. For political reasons (“gambling is a sin”) and regulatory reasons (gambling is regulated, skill contests are not), the DFS sites want to be considered skill games sites. There’s another reason that DFS sites don’t want to be considered gambling: the wagering excise tax.

The wagering excise tax is either a 0.25% or 2% tax on bets made on certain activities. It falls on wagers on sports events or contests, wagers placed in a wagering pool that involves a sports event or contest (if the pool is conducted for profit), and lotteries conducted for a profit. The tax is on the gross amount of wagers received, not the amount someone might win. Would this tax apply to DFS if DFS is considered gambling?

We can look at the Tax Code and the regulations promulgated under the Code to determine this. A wagering pool conducted for profit includes any method or scheme for the distribution of prizes to one or more winning bettors based on the outcome of a sports event, a contest, or a combination or series of such events or contests, if the wagering pool is managed and conducted for the purpose of making a profit. (Regulations 44.4421-1(c)(1) and 44.4421-1(c)(2)) DFS clearly meets the definition of a wagering pool.

So what’s a contest? Regulation 44.4421-1(c)(3) states that includes any type of competition involving speed, skill, endurance, popularity, politics, strength, appearance, etc., such as a general or primary election, the outcome of a nomination convention, a dance marathon, a log rolling, wood-chopping, weight-lifting, corn-husking, beauty contest, etc. Clearly, a weekend of NFL games (or anything else that DFS contests/bets are based on) would qualify.

You may have noticed there are two different tax rates (0.25% and 2%). The 0.25% tax rate applies on any wager authorized under the law of the state in which accepted (IRC § 4401(a)(1)), otherwise the tax rate is 2% (IRC § 4401(a)(2)).

It’s pretty clear to objective observers that DFS is a form of wagering (aka gambling). If that conclusion is accurate, the DFS sites will owe the wagering excise tax.

The Future of DFS

Sunday, October 18th, 2015

If you watch any sports television, you’ve almost certainly seen commercials for the two leading daily fantasy sports (DFS) sites, DraftKings and FanDuel. Last week the Nevada Gaming Control Board announced that DFS is gambling under Nevada law. The Nevada Attorney General’s office released a 17-page review of DFS that thoroughly explained the reasoning. What does this mean for the future of DFS in both Nevada and the US?

First, none of this should have been a surprise. In February 2014 I wrote,

Unfortunately, many states look at just an element of chance to determine if something is gambling. And there’s no doubt that daily fantasy sports have such an element. The problem is that these sites are starting to bring in large dollars. That attracts attention, and some state attorney general is going to wonder the same thing that I am. He or she will conclude that the Duck Test applies and that these are gambling sites in violation of his or her state’s laws. [emphasis in original]

Nevada is not going to be the only state that concludes that DFS is gambling. The head of the Michigan Gaming Control Board has publicly stated that DFS is gambling. Other states will conclude that under their laws that DFS is gambling and either needs a license or should be banned from the state. Nevada may have been the first state to draw this conclusion but it will not be the last.

The problem is how regulators look at something new. Generally, the view of a regulator is that if it hasn’t been made expressly legal under the law that it should be (and is, in their view) illegal. The mindset of most regulators will start with a “DFS is illegal” view. In my first job I learned that perception of reality is far more important than the reality itself. This does not bode well for DFS.

Meanwhile, there’s a federal grand jury investigation of DFS that’s ongoing in Tampa, Florida. This has caused some operators to pull out of Florida. While the DFS sites have proclaimed that the UIGEA (the Unlawful Internet Gambling Enforcement Act of 2006) made DFS legal, the analysis of the Nevada Attorney General puts a stake in that argument. DFS is exempted from the UIGEA but not from other federal and state laws related to gambling.

There’s also a huge risk for DFS from the IRS. What if the IRS concludes that DFS is gambling and that instead of issuing Form 1099-MISC’s to winners they should issue Form W-2Gs? This would be a national conclusion, and give a prima facie case that DFS is gambling. And this could easily happen.

There’s also reality: the duck test. If it looks like a duck, walks like a duck and quacks like a duck, then it just might be a duck. Many DFS participants view it as gambling. Apparently the executives at DraftKings share that view (see the Nevada Attorney General’s report). In the United States gambling is regulated at the state level (along with the federal level). Unless authorized by a state, most gambling in that state is illegal. DFS has not been authorized by any state. (The Massachusetts Attorney General recently stated that DFS was legal in that state. However, it has not been expressly authorized.)

So where does that leave DFS? Someone I know said, “In like 25 years when everyone with any power will have grown up with the Internet, will things be different?” That’s easy to answer: Yes. But we have to live in today’s world, not what it will be in 2040. I expect DFS to follow two different paths in the majority of states. Some states will simply declare it as gambling, making it effectively illegal in those states. Other states will tacitly declare it as gambling but allow regulation of the activity. There will be a minority of states that allow DFS to continue as an unregulated activity. Where one month ago you could play DFS in 45 of the 50 states, that number is down to 42 to 44 states (depending on the DFS site). I expect that number to continue to fall.

Could federal regulation happen? Certainly, but not out of this Congress in the next year. This isn’t a major issue for either party, and 2016 is an election year. Additionally, it’s possible that the next Speaker of the House will be Jason Chaffetz (R-Utah); he’s definitely not pro-gambling. There’s a better chance of the IRS budget being increased (and that has just about a 0% chance of happening) than pro-gambling (or pro-DFS) legislation passing Congress.

Overall, I’m painting a bleak future for DFS in the United States. Maybe I’ll be proven wrong, but the signs are there. Perhaps it was P.T. Barnum who said, “All publicity is good publicity.” (Like the duck test quote, this, too, has been attributed to many individuals.) The advertising and publicity have helped DFS short-term profits. The current publicity has not, though, helped DFS’s future.

How Should Multiple Buy-Ins for a Poker Tournament be Handled on a W-2G?

Wednesday, September 9th, 2015

Poker tournaments today have various forms. Some are “freeze-outs,” where you can only buy into the tournament once. Some have rebuys and add-ons, where if you lose all your chips you can rebuy into the tournament and if you’re in the tournament at a certain point you can purchase an “add-on” of additional tournament chips. A format that has grown in popularity is the multiple reentry tournament. Here, if you lose all your chips you can reenter the tournament. The difference between this and a rebuy tournament is that in a reentry tournament you pay the house fee for running the tournament; in a rebuy tournament, your rebuy goes exclusively into the prize pool.

The IRS Office of Chief Counsel issued an opinion
back in July (but released last week) on how to treat multiple buy-ins for a poker tournament vis-a-vis issuing W-2Gs. Do note that this is solely the opinion of the Chief Counsel’s office; a court could make a completely different ruling. That said, the analysis looks correct to me.

The issue the IRS counsel needed to answer was, “Whether multiple buy-ins should be deducted as individual wagers or in the aggregate from winnings in a poker tournament for the purposes of reporting the winnings on a Form W-2G?” The conclusion the IRS came to is that multiple buy-ins are not identical wagers and should not be aggregated. Although this is a bad ruling for recreational gamblers, I think the IRS got it right.

So when a person rebuys is it an identical wager? “Of course it is, Russ; the person is paying the same amount for the entry into the tournament.” Yes, that’s correct but is his situation identical?

The IRS noted that the preamble to Treasury Decision 7919 explains the rule on identical bets.

…winning on identical bets must be aggregated to determine if the $1,000 floor has been exceeded. This ensures that bettors are treated the same, whether or not a wager is divided into several small components. Identical bets are those in which winning depends on the occurrence (or non-occurrence) of the same event or events. For example, two wagers on a horse to win a particular race general[ly] are identical. … [But] … wagers containing different elements, e.g., an “exacta” and a “trifecta” are not identical.

The issue is that the conditions when you reenter a poker tournament are not identical. Consider if you buy-in before the tournament begins, and there are 100 entrants. When you reenter, there are now 120 entrants. The prize pool is different, your chances of winning are different, and, most likely, the opponents at your table will be different. While the amount wagered is identical, the wager itself has a different chance of success.

The conclusion the IRS draws is correct:

Multiple buy-ins into a single poker tournament event are not identical wagers and therefore should not be aggregated for purposes of withholding and reporting requirements under section 3402(q) and the regulations thereunder. If a player wins a prize at the close of a tournament, only the buy-in that resulted in the win should be deducted from the winnings to determine the “proceeds from a wager.”

While I agree with the conclusion, this is not good for players (or for poker). First, for professional gamblers this is a non-issue. A professional gambler nets his wins and losses, so while a W-2G may have a larger win, the professional gambler can offset that by his higher losses. Nothing has changed for him or her.

However, the situation is different for amateur gamblers. An amateur gambler cannot not his wins and losses. Wins are Other Income (line 21, Form 1040) while losses are an itemized deduction on Schedule A. This ruling will cause an amateur gambler’s Adjusted Gross Income (AGI) to increase. An increased AGI has numerous deleterious effects, including (but not limited to):

  • You lose the value of exemptions;
  • You can lose certain itemized deductions both directly (2% AGI, 7.5%/10% AGI restrictions) and through the phase-out of itemized deductions (note that gambling losses are not impacted by this);
  • You can lose the ability to deduct student loan interest;
  • You may lose tax credits for health insurance; and,
  • Some states do not allow deductions for gambling losses, so if you’re a resident of one of those states you must pay tax on artificial “wins”.

Personally, I think that the reentry format is bad for poker. (A discussion of that has far more to do with the health of the poker economy than taxes.) This ruling from the IRS appears to be legally correct but is another blow to amateur players.

Fail, Caesar! Update

Thursday, July 23rd, 2015

Yesterday US Bankruptcy Judge Benjamin Goldgar ruled that various lawsuits against Caesars Entertainment can go forward. Caesars Entertainment Operating Company (CEOC) is already in bankruptcy; this ruling increases the chances that Caesars Entertainment Corporation (CEC) follows CEOC into Chapter 11.

“‘There is now the potential that this bankruptcy can get very litigious, complex and long,’ said David Tawill, president of the Maglan Capital hedge fund.”

So what does this mean? First, I don’t think there’s potential that the bankruptcy will get very litigious, complex and long; rather, there’s near certainty that it will. I earlier wrote that the bankruptcy would take “a long time” to resolve; I think that’s certain.

Additionally, that the other lawsuits are going forward is bad news for the current owners of CEC. Imho, they were hoping that they could create a “bad” company, get rid of a ton of debt, and emerge from Chapter 11 with something of value. That’s now less than an even bet.

Instead, the lawsuits are likely telling the truth: That CEOC was created as a way of shuffling assets. This means it is now more likely than not that the rest of Caesars will end up in Chapter 11.

That would put a stop to the lawsuits. It would also mean the current majority owners of CEC (Apollo Global Management and TPG Capital) will see the value of their investment go towards $0. It could also mean that some of the current assets of Caesars will end up being sold. The big problem with Caesars is their debt load. Bankruptcy will get rid of the debt, and many of the underlying assets have substantial value.

One last certainty: The lawyers involved will be making plenty of money.

FBAR Due in One Week

Tuesday, June 23rd, 2015

The Report of Foreign Bank and Financial Accounts (Form 114, the FBAR) is due on June 30th. The form must be electronically filed with FINCEN. Your tax professional may be able to do it through his software (we can) or you can do it yourself using the BSA EFile system. There is now an online form you can use (besides Adobe reader) that may work better (it certainly can’t work worse).

Because of the Hom decision of last year, we now must again report foreign online gambling accounts. That’s basically all online gambling sites except the legal sites in Delaware, Nevada, and New Jersey. I maintain a list of online gambling sites and their mailing addresses here.

There are ridiculous penalties if you willfully fail to file an FBAR (half the balance in the account or $100,000 (per account), whichever is greater). Thus, as I said last year, just file the FBAR…timely.

Form 8300 and Poker

Wednesday, June 17th, 2015

I’ve posted before on staking, but someone asked me the following question:

I’m a professional [poker player] and am going to be staked for the High Roller One Drop Tournament [a $111,111 buy-in tournament]. I’m going to be handed the cash to enter the tournament. What do I need to do?

Besides the normal staking issues (see these articles), there’s another issue: cash reporting. If you’re a business and you receive a payment of $10,000 or more in cash or like funds (this would include casino chips but would not include a cashier’s check), you have a reporting requirement: You must file Form 8300 with the IRS.

A professional poker player is operating a business and is required to comply with the laws impacting businesses. This includes cash reporting requirements. You have 15 days from the date of the cash transaction to report it. This is done by either mailing Form 8300 to the IRS or by filing it electronically through the BSA efile website. Note that if you use the BSA efile system you will have to register (required for Form 8300 efiling).

Like most penalties related to the Bank Secrecy Act, the penalties are on the ridiculous side. While the Failure to File penalty is just $100, the Intentional Failure to File penalty is the greater of $25,000 or the amount of the cash transaction (to a maximum of $100,000).

The IRS does take questions regarding Form 8300. You can call the IRS at 866-270-0733 or email questions to