Teaching Tax Flow: The Podcast

0:00:08 - (John Tripolsky): Welcome back, everybody. Episode 69. Today we are going to dive headfirst into gambling and taxes. But before we do that, it why don't accountants like to gamble during tax season? Well, because they don't want to risk losing their assets. Enough of the corny jokes. Let's take a moment, as always, and thank our sponsor on this episode.
0:00:40 - (Ad Read): This podcast is sponsored by Reps Tracker. Are you a real estate investor who is bogged down with a huge tax burden? Real estate investing can open the door to powerful tax benefits. Reps tracker can streamline the process of accelerating these tax benefits. To take advantage of a special TTF community discount, go to ww repstracker.com slash affiliate teachingtaxflow and use the code IFG. You can look in our show notes or email us at hello@teachingtaxlow.com
0:01:11 - (John Tripolsky): hey, everyone. Welcome back to the Teaching TaxFlow podcast. We know you're here because you like to bet on yourself, bet on your success. But did you know that some forms of gambling are actually beneficial in a sense, or losses? Wins, obviously are, too, when it comes tax time. So, Chris Pacuro, welcome back to the party, my brother. Let's talk about this topic today, shall we?
0:01:37 - (Chris Piccuirro): Great to be back, and it's Super bowl week. John, I know you're not a big football fan, but there was a rare instance that you got interested in football because the Detroit Lions came very close to making the Super bowl. It actually piqued John Tripolski's interest. And there was actually sports watched other than Detroit Red Wing hockey in your household, I bet.
0:02:04 - (John Tripolsky): And, you know, know, I'm glad you let in with that. So let's talk about that for a second. So, yes, I am not a football fan, and not because I don't like it just because obviously we play in hockey forever. But yes, I was a Lions fan for a couple of weeks there, which I'm one of those guys that hopped on the bandwagon, which then proceeded to pique my interest in fan duo. So I got on there and man, I've never lost $200 so quick in my life.
0:02:30 - (John Tripolsky): I thought I had a good thing going for me going to the beginning of the game, and out they go. So, that being said, how in the world does this actually relate to taxes? People are probably wondering, like, oh, wow, is this a gambling or a sports show? Now, what in the world's going on? And Chris, I remember we talked about this briefly. This might have been a year ago. You brought up the topic and it was almost like, hey, John, did you know?
0:02:54 - (John Tripolsky): And I seriously sit there and shook my head for a minute. I'm like, what in the world are you talking about? Like, how are these two correlated to each other? So I would wager a bet. Here we go with that again. That probably 99.45% of people have no clue what we're about to tell them. Does that sound about right? What do you think?
0:03:19 - (Chris Piccuirro): Well, you know what, John? I would take the under on this bet. And I bet more than 5% of people know about gambling. But we're here to talk about since it is Super bowl week, congratulations to the Kansas City Chiefs and the 49 ers should be a boo.
0:03:43 - (John Tripolsky): Boo from Detroit. Boo from Detroit. There we go. We need a soundboard when we do.
0:03:49 - (Chris Piccuirro): This show, by the way, you've got to develop that. It is the most wagered on sporting event, single day sporting event of the year. I'm 99% sure. Get another gamble by saying this on a podcast. I know we had the NCAA tournament as a longer event and you've got the Kentucky Derby, but it's interesting because there's a couple of different factors that have really moved gambling into the forefront of tax.
0:04:20 - (Chris Piccuirro): It's such a big issue that I'm very fortunate to be an instructor for the National association of Tax Professionals. So I get to go travel a little bit in the fall and teach other tax pros about tax updates, with tax season updates and such. And one of the topics we discussed was gambling winnings and losses and how you handle it on your tax return. So now that gambling is so know, it used to be you'd go to the casino in Vegas or you'd fly down to Mississippi or something like that, where gambling was done in many, many states allow online wagering and app based wagering. So just like yourself, you got bit by the bug.
0:05:07 - (Chris Piccuirro): You went onto an app and legally wagered and probably lost. We're going to talk about your situation in a moment on a sporting event. So now with all of that going on, so the legality of online wagering and the advanced reporting that's going to be coming down in 1099 and that sort of stuff down the road, that's why it's important to understand that gambling income needs to be reported on your tax return. And it could be something super innocent like, oh, I'm not going to name any of the apps because they should be a sponsor for naming them but I was in XYZ app.
0:05:47 - (Chris Piccuirro): I played a daily fantasy football contest, and I won $2,000. Let's say that person prepares their own return, or they go and have it professionally done and they honestly forgot that they won that money. They might have won it in January, 1 week of February, and it's over a year later, and they now, Andrew Poohols is probably snickering somewhere listening to this. Might get an IRS notice, because that's going to get reported to the IRS.
0:06:18 - (Chris Piccuirro): And the IRS, at some point as they ramp up their enforcement is going to say, you didn't report these winnings. So let's talk about the basics of gambling, winnings, losing, and what we're going to do on your tax return to report them. So we're going to start by just identifying your common types of gambling, either in person or online. And those are going to be not limited to bingo, lotteries, blackjack, poker, card games like this, dice games. Now, John, this isn't you shooting dice in the mean streets of Chelsea.
0:06:59 - (Chris Piccuirro): I know you'd love to do that. You got a little posse together. But these are games like roulette.
0:07:04 - (John Tripolsky): We get a little rough out here, man. If we did that here in our town, it would be probably four guys, I would say from 19 years old to 65. A couple had a cattle, a couple of chickens, maybe a llama here or there. It'd be a very interesting game.
0:07:21 - (Chris Piccuirro): Well, good segue, because we're going to talk about non cash winnings. So if you do win that llama, we'll discuss that at the end of the show. So, like I said, slot machines.
0:07:33 - (John Tripolsky): Now, we're betting on livestock here, folks. We are betting on livestock, something called paramutual betting.
0:07:41 - (Chris Piccuirro): What's that? Well, horse and dog racing. You can actually wager on the results of an election. These are real things. So esports betting, I mean, there is a lot of different aspects of gambling, and you could even win real currency or virtual, or in game currency, like points and coins and credits and just a little tidbit. If you do win virtual currency, as long as that virtual currency stays in the game, then the IRS has ruled that that is not gambling activity. So, for instance, if you play XYZ video game and you accumulate a crapload of virtual currency, as long as it stays in the game and it can't be monetized, then it's not considered virtual currency.
0:08:35 - (Chris Piccuirro): So any type of gambling winnings, either here in the United States or even offshore, is taxable for us residents. So first thing we need to understand in our basics of gambling. IRS considers all gambling winnings as taxable. John, your dice game, I hate to break it to you, regardless of if they come from legal or illegal gambling activities. So if you're talking to your cousin Guido and he's booking your bets on a napkin with a coffee stain, that is, although illegal, that is gambling. And if you win, you should be reporting that on your tax return.
0:09:18 - (John Tripolsky): I'm sure Guido wouldn't like it. He's a pretty established street bookie. Yeah, he might get popped here. You never know. I mean, he is giving out llamas at the end of the day, so that could be exactly a big problem.
0:09:35 - (Chris Piccuirro): But any type of gambling winnings is taxable, again, illegal or legal, and that is at worldwide gambling. So if you, John, I know you live in, and we both grew up right outside of Detroit. 2025 minutes drive. Before, it was a pain to go through customs to get to Canada. So, Windsor, Ontario. And I like to go to the Sarnia, Ontario casino back in the day because there are less people. If I went to Sarnia and won $1,000 canadian, that would be taxable in the United States based on whatever the exchange rate was that day, I would have to report that on my us tax return.
0:10:15 - (Chris Piccuirro): I would get a credit if I had to pay any canadian tax. But the point is, worldwide gambling winnings for us tax resident are taxable. Now, those foreign tax credits still apply.
0:10:29 - (John Tripolsky): So here's a question for you, actually, Chris. So for those of our friends that are out there, those that are listening, right? So say you do go to a casino, wherever you partake in your gambling. Is this one of those scenarios where us that are self employed or somebody that receives a 1099? Right. You kind of sit there, twiddle on your thumbs at the beginning of the year waiting for that to come in. I mean, is this something that you literally just keep your tabs on and say, hey, time for me to complete my taxes or file my taxes. Here's the number, let's pop it in the form and go that way? Or is it something that you almost have to wait for the casino or wherever to issue you a document to then take to your tax professional? How does that work? Is this something, basically what I'm getting at is, come tax time, whose court is the ball in when it comes time to file this specifically?
0:11:28 - (Chris Piccuirro): Great question. So it's your responsibility to report all your gambling winnings. Okay. So we know that regardless if you get a 1099 or not, most gambling winning are reported on a form w stands for gambling. Wow.
0:11:47 - (John Tripolsky): I thought it was Guido.
0:11:51 - (Chris Piccuirro): Although I bet if you don't pay him, he's going to issue you a pair of cement shoes.
0:11:59 - (John Tripolsky): That's how, you know, we both grew up in the metro Detroit area, right? We always make these mafia references, and here we are. We didn't know we were both going to say concrete or cement shoes. And here we go. But anyways, I rest my case.
0:12:12 - (Chris Piccuirro): Right. So typically what's going to happen is you will be issued so any type of winnings, generally any winnings that are $600 or more from one gambling activity, the payer or the casino, or will issue you a form w depending on. Now, some states require the casino. Let's say you go to Mississippi, John, and you hit a slot machine for $2,000. What happens is someone comes over, they take your slip, they take you back to the office.
0:12:47 - (Chris Piccuirro): You feel like you're at the finance manager of an auto dealership's office, or I should say the person that's going to sell you that extended warranty. Right. And we've all been there. And then they're going to get your information, they're going to need your Social Security number, and they're going to issue that w 2g because it's over $600. They're required by the IRS to issue that to the IRS. And at that point, you can have tax withholding from it. Some states require you if you're a non resident.
0:13:14 - (Chris Piccuirro): So if Mississippi is like, this bozo is from Michigan, he's never going to report this $2,000 worth of income in the state of Mississippi. We're going to withhold Mississippi tax on that w two. And now you will have to file a Mississippi state tax return to try to get some of that withholding back. Now, in your case, you're a Michigan resident, so you would actually get a credit on Michigan for the Mississippi state tax paid.
0:13:35 - (Chris Piccuirro): The point is, in general, most w two g's are issued on the spot when you're there, when you're at the casino. Now, online gambling. So if you use your favorite app, they're not going to issue you a w 2g every time you win over $600. They're going to most likely issue you a form at the end of the year, or you're going to need to go back and export or download all of your activity. So that comes down to record keeping.
0:14:04 - (John Tripolsky): And actually on that, too. Speaking of record keeping, we did talk about that in a previous episode, too, which I think is important to mention here, before we forget, is that anything that's issued via email, right. That's a big thing. So really watch your subject lines. I mean, I've seen a couple come across my desk this year already, and they're doing a much better job of really capitalizing and emphasizing what is in that email, and it's not junk mail, so they're sending those watch it. It's very important.
0:14:33 - (Chris Piccuirro): It's very important. So the thing is, sometimes people come in with a stack of w two g's to their tax preparer. My best advice is if you're in a situation, this is common to some where someone is an avid gambler. Now there are special rules that go beyond this podcast when gambling goes from a recreational activity to an actual business related activity. And you would move the reporting off to what's called a schedule c.
0:15:09 - (Chris Piccuirro): That's very rare, but that could happen. But let's say someone has just a ton of gambling income, so they're not a professional gambler. It's very rare someone is a professional gambler versus regular or casual, a recreational or casual gambler, according to the IRS. But let's assume you're a recreational gambler. You might be a casino junkie, that's what you like to do. And you might not have all your w two g's for the year. It's at that point we would recommend someone, and we do have someone in the teaching tax flow community that can help you out.
0:15:55 - (Chris Piccuirro): At that point we recommend you actually pull your IRS transcripts. What that means is that when that w two is issued to you by the casino, a copy goes typically electronically to the IRS when it's time for tax preparation. If you're uncertain, if you have all the w two g's, you can pull your transcript and it'll lay out all of your w two g's for you.
0:16:19 - (John Tripolsky): Basically gives you your roadmap that is sent.
0:16:21 - (Chris Piccuirro): It does give you a roadmap balances. But let's jump to record keeping. Proper record keeping is essential when you're dealing with gambling income and deductions because we're going to go back to record keeping. Remember I said gambling income, I know we're talking to the federal level, is considered taxable. You can deduct your gambling losses up to the amount of gambling wins if you itemize your deduction on the federal return.
0:16:51 - (Chris Piccuirro): So you can offset your winnings with losses, but you can't deduct more in losses than you report in wins. All right, so if you won, John $10,000 and because you were on a bender in Vegas, you threw it all back in the casino, the slots, and you lost ten grand. You would have to report $10,000 of income on the federal return. And if you itemize, you'd deduct $10,000. The trouble is there are a lot of tax credits and calculations and even state tax assessed on your adjusted gross income, meaning versus your taxable income. So you actually could be paying.
0:17:30 - (Chris Piccuirro): Doesn't mean you're going to get those deductions for the gambling losses on your state tax return. So gambling losses are the most common question is, can I deduct losses? Because everyone talks like that.
0:17:40 - (John Tripolsky): Right, right. And you did mention something really good too. That I do want to emphasize again. Just like the subject line of the emails is, you mentioned only if you itemize your deductions. This is an option, right? We did a whole podcast on that earlier, too, if you're interested in that one. Great show. I'll put the link actually in the show notes here as well. We reference a lot of cool things like, hey, should I make a donation to goodwill, Salvation army, or should I garage sale this, et cetera.
0:18:11 - (Chris Piccuirro): Great, right?
0:18:12 - (John Tripolsky): Just wanted to touch on that again too.
0:18:14 - (Chris Piccuirro): So what record keeping is required now? There's some apps out there. There are some people that do not like to get a casino club card or any type of, if they go into their favorite casino, a card that tracks their ins and outs. The advantage is you have a built in bookkeeping system there, right? And you might end up buying yourself a $300 hamburger. Hey, you lost $300, but we're going to give you a $20 credit to the restaurant, and you can't use it on alcohol. So go get yourself an overpriced hamburger. But for record keeping, you have to have the proper record keeping to deduct those losses. So that means that you're including what type of activity you're engaged in, the date, location, amount won and lost, and supporting documents like receipts or tickets.
0:19:03 - (Chris Piccuirro): You will need these in case of an IRS audit. Now, it goes beyond the scope of this podcast, but if you are an avid slot player, there are special rules when you're dealing with reporting slot activity in what is considered a quote unquote session. So again, if you are avid slot player and you're confused about those special rules, please jump into our private Facebook group defeating taxes, and we're going to happily guide you in the right direction.
0:19:36 - (Chris Piccuirro): So definitely keep those records. What is my tax rate on gambling? It's whatever your marginal tax rate is okay, but be careful. I've seen situations where someone has a modest pension of 12,000 a year, they get Social Security. So none of they have no taxable income. Their Social Security is not taxable and they're under $12,000 of income is not taxable because they're under the standard deduction. They had a $40,000 pot.
0:20:06 - (Chris Piccuirro): Now guess what happens. That 40 grand is taxable and a good portion of their Social Security is taxable. So their marginal tax rate is actually high. So marginal tax rate is what you're paying tax on for your gambling winnings. Now, state tax, state and local tax, in addition to federal taxes, you might owe state and local tax on the gambling winnings. And that depends on where you won the money and what state you reside in. So John is a Michigan resident. You have the honor of paying state of Michigan tax on all of your income. Even if you bozone around and went down to let's put you in Missouri, right, because they have a state tax, you go to the riverboat there, you hit a $3,000 slot.
0:20:56 - (Chris Piccuirro): You owe Michigan tax on that. And Missouri will say you owe us tax on that too. But remember, as I said before, you're not going to get double taxed. You'll get a credit in Michigan for whatever Missouri tax that you pay.
0:21:09 - (John Tripolsky): And Chris, does every state kind of have that? I don't know the term specifically, but almost an agreement or an alliance with that. Is that all 50 states that allow for that?
0:21:20 - (Chris Piccuirro): Off the top of my head, I'm not going to say for sure. I don't think all 50 states have the state tax credit. But the vast, it's very rare that a state doesn't have a credit for tax paid in another state if you're a resident.
0:21:37 - (John Tripolsky): Makes sense. And then even for our states. And again, a question. I don't know the answer. Even so, we're talking about state tax, right? So do you guys have casinos in Tennessee as well or are you guys a casino free state?
0:21:48 - (Chris Piccuirro): We do not have know in the bordering mean. As you know, John, I'm about an hour drive to Kentucky. Alabama doesn't have it. Maybe an hour and a half if I went northwest to Indiana. But we don't have casinos. We do have legal gambling on apps. So online? Yeah, computer and online.
0:22:12 - (John Tripolsky): Gotcha. Gotcha. And I was wondering too with that one. I wonder if so say there is a casino in a state, say without state tax, if there are any of that. Actually, yeah, there's a couple, like, they go, so say you're playing it there. You're at a casino, being that there's no state tax and I'm totally throwing you out on the spot when I do not expect you to know the answer to this one. If you do, awesome. If not, totally fine.
0:22:36 - (John Tripolsky): I wonder, would those casinos still issue that? Was it a w nine g? Is that what that was? Would they issue that on the spot? Or are they kind of like, all right, guy, you're on your own, you deal with the feds.
0:22:50 - (Chris Piccuirro): Well, typically what's going to happen is the w 2G, it's a federal tax form, so that's going to be required. So let's say you go to Vegas and you hit a slot. What's going to happen is you're going to get a w 2G. It's going to be reported to the IRS. It's at that point you can determine if you want to have tax withholding or you're going to voluntarily pay tax in the future. And it's at that point they ask where your residence is because they're going to need your id, your Social Security number, and they probably send that to the state of Michigan now. And you're required to pay tax in the state of Michigan as a Michigan resident on that.
0:23:29 - (Chris Piccuirro): I don't know how aggressive the state of Michigan is in actually following up with that. I would say 99.9% of the time you're going to pay tax on it, because what happens is you're taking your adjusted gross income from the federal side and you're moving that on your estate tax return, and then you would have to reduce that income. But there's no way to reduce that income if you're a non resident.
0:23:53 - (John Tripolsky): If you get issued one of those at a casino, if you're having a good old time and they keep giving you liquid courage, it's not an extra bar napkin that they've probably given you. If they print it out for you, make sure you hold on to that thing right.
0:24:06 - (Chris Piccuirro): And I have one more thing to close on because you mentioned it. Non cash winnings. So if you receive a non cash prize from gambling or even a game show or a radio show, like you win a trip to the Super bowl, not to pour salt in your wounds, john, such as a car, vacation package, or other goods, the fair market value is considered taxable income and must be reported to the IRS. And that's based on the retail value of the prize. So if you win a car at a casino, you will pay tax on whatever the fair market value of that car, you.
0:24:44 - (Chris Piccuirro): So you could either sell the car, I guess, or keep it. I mean, still a good deal. I'll take the that. So if it's a llama or whatever the heck you have going on in Chelsea, you will pay tax on the fair market value of what?
0:25:00 - (John Tripolsky): And this brings up another one of my hairbrain questions. Right. Hairbrain ideas. So I've seen those ads that have been out there, right? It says, hey, we're going to give you a vehicle, a seven day cruise with all expenses and taxes paid. So technically with them saying that by them paying the taxes, is that payment on your taxes actually taxable?
0:25:26 - (Chris Piccuirro): No, I think what that means is they're paying all of the travel taxes, the occupancy taxes, just like when you go to a hotel or rent a vehicle, it's still taxable income unless they take the value of that trip and then are so generous as to figure out how much your taxes on your federal return and mail that in, which I think would be very rare.
0:25:45 - (John Tripolsky): That makes sense.
0:25:46 - (Chris Piccuirro): Okay.
0:25:46 - (John Tripolsky): That makes sense. Yeah. I told you it was a hairbrain question. Hairbrain idea. But hey, Texas are taxes and taxes are not all taxes. So that being said, Chrissy gave us a good roadmap, a good layout for what people can expect. So now, going into the Super bowl, hopefully everybody that is listening to this can know, is it really worth betting on it? How confident are in your answer, how much do you want to pay in tax? So that being the case, too, if you do happen to strike it big and nobody wins the Super bowl because the Lions aren't in it, we're just going to say nobody's going to win.
0:26:25 - (John Tripolsky): Game doesn't exist. Think about that. So there's that impact, right? Come tax time. So it's not just free money. You're not walking around with a bag of bitcoin, proverbial bag of bitcoin or a bunch of quarters from, from Guido Giuseppe sitting on the corner. So think about that. Everything you do financially does impact your taxes in some way, shape or another. And here at teaching taxable and also on defeating tax, our private Facebook group, as Chris always likes to say, our mission is actually, Chris, why don't you go ahead and say what our overall mission is here at TTF? What are we trying to do for everybody?
0:27:08 - (Chris Piccuirro): We are trying to legally and ethically reduce the tax you pay in your lifetime. Enjoy the Super bowl. And John, I'm going to take it away this time.
0:27:19 - (John Tripolsky): Do it up, man.
0:27:20 - (Chris Piccuirro): We look forward to seeing you the same time, the same place next week.
0:27:26 - (John Tripolsky): Very good, sir. Very good, sir. 
Thank you, everybody, for hanging out with us once again this week on the episode of the Teaching Tax Flow podcast. Chris actually wrapped it up for us this week. Little bit of change. I'm all about change, but I don't like to lose change, pocket change at the casino, or I should say betting against the Lions in the Super bowl. So clearly I'm still a little sour about that. We'll leave that one as it is.
0:28:01 - (John Tripolsky): But if you are going to partake in those gambling efforts, we can call them this week. Now you know what to do with it. Win or lose, you know what the outcome is going to be on your taxes and how that affects it. So as promised as well, no more corny jokes. We started off with one. We're not going to wrap up with one. So I am going to shut my mouth, let you guys get down to it a couple more days this week before the big game coming up on Sunday.
0:28:28 - (John Tripolsky): Enjoy it. But the friendly reminder we don't refer to as tax season around here because tax planning consists of every day on the calendar. So consider that is all your friends are freaking out, running around rampant, saying, oh my gosh, I have until April 15 or so this year. I got to get my taxes in. Got to get my taxes in. You sit back and maybe relax a little bit, kick your feet up. But also don't delay too much on planning. So any questions on that tax planning or preparation?
0:29:02 - (John Tripolsky): Give us a jingle. Shoot us a message on Facebook, LinkedIn, on the website, email, however you prefer. Drop us a line. We're here to help, and we'll see everybody next week.
0:29:18 - (Disclaimer): The content provided is for educational purposes only. We encourage you to seek personalized investment advice from your financial professional. For all tax and legal advice, please consult your CPA or attorney. Investment advisory services are offered through cabin Advisors, a registered investment advisor. Securities are offered through cabin Securities, a registered broker dealer. The content of this podcast does not constitute an offer of securities. Offerings can only be made through an offering memorandum, and you should carefully examine the risk factors and other information containing the memorandum.