But if you win $5,000 at the slots one day but then take a $5,000 gambling loss later that year, you can use that loss to cancel out your winnings and avoid paying taxes on them. Many people seek to avoid paying taxes on as many things as possible, including gambling winnings. However, gambling winnings are considered a taxable income and must be reported when filing your taxes. All cash prizes, in addition to the value of other winnings, are taxable by the federal, and sometimes, state governments.

It’s a scene many poker players dream about. One lucky player has outlasted thousands of others and now sits in front of a mountain of poker chips as his friends gather around posing for pictures and celebrating a six-figure score. Champagne will flow and the smiles will go on for hours. Clubs and bars might be visited on Sin City’s famous strip as the celebration continues.

But the most important visit for a poker player coming off a big score might be to an accountant, as the tax implications from a win like this can hurt if not handled properly.

The card-playing world is rife with overnight millionaires — young savants who win it big on the poker felt or grind away at cash games earning a nice living. Unfortunately, there are just as many players who see their fortunes plunge after living the high life. In the poker world, the cash can come easy, but keeping it is a different story. With the U.S. tax filing deadline on April 18, PokerNews takes a look at the unique challenges facing gamblers and the best ways to plan for the future.

THE TAX MAN

It’s another scorching day in the Las Vegas desert, but cool inside the Rio as thousands of players battle it out. In the halls of the Rio convention space, CPA Ray Kondler mans a small booth as a couple players ask him questions about their tax liabilities and how best to prepare. Kondler has been in the same location for the last six years — working with players and promoting his firm and its specialization in helping poker players and gamblers. Plenty of players utilize his service and expertise in all tax-related poker matters.

“I love it – it’s so much fun being here. We have a ball,” Kondler says of his time at the WSOP each summer. “We meet so many people. It’s an interesting niche because they’re an interesting group. They’re all the nicest guys, they just need some education. People come up to us and want some free advice and that’s what we’re here for.”

After graduating from Seton Hall and working at Arthur Andersen, Kondler began his own firm 26 years ago in New Jersey working with businesses and individuals. Kondler then bought a practice in Las Vegas, which already had some gambling clients. A poker player himself, Kondler saw the explosion in the game’s popularity in the 2000s and saw an opportunity to grow his firm and help players.

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“I play poker and in some World Series of Poker events and realized that there was a good need for a good taxation guy in poker and gambling,” Kondler says. “Now every year it just keeps expanding.”

His firm now boasts several major winners including the Main Event (the most famous tournament in poker) winners and numerous players who have won $4-5 million. The practice, which now also has offices in Las Vegas and San Diego, now also serves as the auditor for seven Las Vegas-area casinos. The firm serves hundreds of professional gamblers (including sports bettors and daily fantasy sports players) that range from $2-5 cash game grinders to WSOP bracelet winners to high-stakes online players.

First and foremost, Kondler’s role is to educate players. Most don’t realize all the opportunities within the tax code to help them in reporting. They don’t know how to keep records, Kondler says, and don’t know which forms to use and when to file. Many players are more focused on their winnings and their next stop on the poker tournament scene than how best to prepare for filing with the IRS.

“Sooner or later, they’re going to need somebody,” Kondler says. “Even the people that cashed today for $2,000. They won’t get a W2G, but because they do have $2,000 in winnings they’ll have to report. But anything over $5,000 they’ll get a W2G, so then they come to us and say, ‘What do we do?’ We also get the random guy who says, ‘I started a business, what do I do?’ so it’s pretty interesting.”

Randy Cowdery is president of Thoroughbred Tax Service and has been a tax accountant in Las Vegas for 15 years. Crowdery also brings a unique insight into the industry. When he was 18 in the mid-1970s, he started counting cards playing blackjack to earn spending money in college. After graduating he only played recreationally, but became a full-time advantaged video poker player for three years after moving to Vegas in 1999. He then decided to put his accounting minor in college to use and become a tax accountant in 2004.

“From the beginning I specialized in gamblers’ tax returns and I now have clients throughout the country and still a few internationally that left the U.S. because of Black Friday (the day in the U.S. when the feds shut down online poker),” he says. “My recreational and professional gamblers include poker and video poker players, horse bettors, sports bettors, and blackjack players. Professional poker player returns have increased slightly in recent years.”

Cowdery says the IRS has never looked favorably at gamblers and they face some unique disadvantages. Because recreational players cannot write off expenses and professional players have to pay self-employment tax, he says, the IRS would like to see losers file as recreational players and winners file as professional gamblers.

“The tax code treats recreational and professional players less than fairly in my opinion,” he says. “Recreational players are supposed to report all their winnings as income before considering losses. The losses are then reported as an itemized deduction on Schedule A. This means their adjusted gross income is artificially high on their tax return. For filers that do not normally itemize they can lose part or all of their standard deduction. If your gambling winnings push your income high enough, you can pay additional Medicare tax and the net investment tax along with having exemptions and deductions phased out.”

Cowdery says all of these “taxes” were meant for households with income above $250,000, but recreational players with income far below that threshold and who actually lost money gambling can be subject to them. Additionally, those on Medicare can see their premiums go up more than triple the standard rate even when they’ve actually lost money gambling.

Professional gamblers are also not treated like all other businesses due to gambling losses — they cannot show a business loss on their tax return.

“So where Donald Trump can write off his billion-dollar loss over 20 years of tax returns, if a professional gambler loses a million dollars one year and wins a million dollars the next he has to pay taxes on that million dollars without consideration that he lost that the year before,” he says. “What many professional gamblers and even many tax professionals do not know is that the IRS will allow a loss on the Schedule C for business expenses. Just be sure losses do not exceed wins.”

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MAKING A PLAN

'In order to be a successful gambler you have to have a complete disregard for money.'

While that saying by 10-time WSOP winner Doyle Brunson is fitting for many players at the tables, it also describes many players’ spending habits away from the casino and mental approach to taxes and record keeping.

Sadly, stories of players hitting it big and then going broke are common and many somewhat view “going broke” as a rite of passage in the world of poker. In recent years, stories in the news have included WSOP champions selling bracelets or big-name players owing other players hundreds of thousands of dollars. No doubt, being in arrears to the IRS is a problem some may also face, and some simple planning could helps players avoid some major headaches.

Brunson, who now lives in Las Vegas and has only had two losing years in 61 years playing poker, still plays at some of the biggest buy-in cash games in the world even at age 83. Brunson has made tax preparation and financial management a key part of his life in the game. Many players are extremely leery about discussing taxes, finances, and the IRS, but Brunson offered his general philosophy on the matter to The Accountant.

“The best advice was given to me by Johnny Moss,” he says, referencing another famous Texas poker player who won the first two WSOP Main Events. “Moss said: ‘pay your taxes and invest a small part of your bankroll. Money sitting in lockboxes does you no good, so bite the bullet and pay your taxes.’ That is sound advice and I recommend the same thing. Good luck!”

For poker players and other gamblers, Kondler offers two main points of advice to his clients. First, track everything and leave a paper trail. Whether it’s tournament buy-ins receipts, cash game log books, ATM receipts, or credit card purchases, a player must make sure he or she can prove losses and expenses because it is extremely difficult to piece together an entire year two or three years later in a potential audit.

Second, Kondler notes a bit of common sense — that taxes do not go away. If someone owes money to the IRS, state, or international tax agency, that burden will not go away if ignored. Players must properly plan each year to ensure they can make the necessary payments if necessary.

“Documentation is the main issue faced by players,” Kondler says. “Many of our new gambling clients come to us and have very little in the form of documentation for wins, losses, expenses, money they lent out, et cetera. It is challenging to address IRS notices or even potential audits without proof that any of these things occurred. It is critical to document your play in order to prevent any future hassle.”

Cowdery agrees and notes that it is important for professional gamblers to keep track of every expense and expenditure. Players must treat their “action” more like a business to satisfy taxing agencies in case of an audit or inquiry.

“The biggest problem with gamblers during audits is not having logs,” he says. “The IRS loves logs. They want mileage logs and gambling logs. A mileage log is the best method for a professional gambler to substantiate those miles related to gambling. They also want your mileage for the whole year, so jotting down your odometer at the beginning of every year is important. Of course maintaining a mileage log can be a real pain which is why so many people don’t keep one.”

A gambling log is the primary record that the IRS considers when determining wins and losses. For taxes, this log is important for both recreational and professional gamblers. The log should be contemporaneous – meaning it is updated it at least daily when gambling – and should show date, time, place, wins, losses, and any other information such as a person’s name, machine, or table number to substantiate the log. Cowdery notes that ATM receipts, markers, and win/loss statements are good secondary items.

Another obstacle faced by professional gamblers is that the IRS says mileage to a player’s first location and from his or her last location is considered commuting miles and not deductible.

“There is a way to get around that for professional gamblers,” Cowdery says. “When a taxpayer does not have a regular business location, and typically gamblers do not, then if the taxpayer has a home office that qualifies as your principal place of business and all mileage to and from business locations, casinos, become deductible. But be careful, the IRS considers a home office as a place that is used both regularly and exclusively for business.”

Some players also have unique income possibilities exclusive to poker. Many players often “back” other players in tournaments and even in cash games by buying a percentage of their action. Any winnings derived from the other players’ performance must be included in tax filings. Other considerations include sponsorships and other new types of betting income such as daily fantasy sports, which has become more popular in the U.S. and in other countries.

Beyond tax filing and documentation, Kondler attempts to do more for players by helping them establish long-term saving goals through traditional savings and investment accounts. He also helps highly successful players set up corporations to better work within the tax system. The firm also determines if a player is a player is a pro or an amateur to best file the player’s tax return.

“We try different strategies with players. I have all my investor licenses so we have millions of dollars that we manage every day in the stock market,” he says. “I try to get the guys into 401(k)s and pension plans and things like that. A lot of players win and they don’t keep the money, they go and buy into other guys. We tell them, ‘Hey, I can put the money away for you and manage it.’ A lot guys who theoretically make a lot of money, when we ask them to pay taxes, they don’t have it anymore. Anybody can do a tax return, but our job as a CPA is to teach them other things like how to save money for the future.”

GLOBAL CHALLENGES

Poker is a global game now, and the 2016 WSOP featured players from 107 countries looking for their chance at poker glory. But winning big money can turn into a tax nightmare for some foreign-born players.

A foreign player who cashes in an event will receive an IRS 1042-S, which is used to report money paid to foreigners in the U.S. that are subject to income tax withholding. The form must be filed even if nothing is deducted and withheld from the payment because of a treaty or if any amount withheld was repaid to the payee.

The problem, Kondler notes, is that U.S. tax treatment for players from other countries completely depends on the country of residence/citizenship. The U.S. has tax treaties with certain European countries that state gambling winnings won in the U.S. are immune from U.S. taxation. The money won must be claimed in the country of residence/citizenship, but no taxes are due in the U.S. However, there are only 28 countries worldwide that benefit from gambling-based tax treaties with the U.S., so the rest of the world will automatically have 30 percent withheld from their winnings, and many do not know how to get those refunds returned.

“This is where we can provide assistance to players,” Kondler says. “We can prepare U.S. tax returns for players that net their total winnings against their total losses. For instance, if a player wins $100,000 in a tournament they will automatically have $30,000 withheld by the U.S. government.

“However, let’s say the same player actually had $50,000 of U.S.-based tournament buy-ins, losses, or expenses in the same year. We will file a return that shows the correct net win of $50,000 and the player is only taxed on that amount at the applicable U.S. tax rate, instead of being taxed on the entire $100,000 win. The player is then sent a refund in the form of a check when the process is completed.”

Many players may not realize that this is an option to get back some of those withheld funds. And with so many players making their way to Las Vegas from other countries (last summer’s WSOP featured more than 107,000 entries), this is a tax situation affecting more and more players.

Planning and keeping records are so important for players, Kondler says. A bit of preparation can not only help save money that should not be going to taxing authorities, but save some headaches.

Online Poker And Taxes

“Do your research,” he says. “Reach out to a tax professional if you have any questions about your tax situation. Do not wait until the end of the year because there are things you can be doing now that will end up saving you money in the long run.”

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Sean Chaffin is a freelance writer in Crandall, Texas, and writes frequently about gambling and poker. If you have any story ideas, please email him at [email protected] or follow him @PokerTraditions. His poker book is RAISING THE STAKES: True Tales of Gambling, Wagering & Poker Faces and available on Amazon.com.

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