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This is Agent Provocateur with Allan Walsh and Adam Wild.

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Welcome to another episode of Agent Provocateur. Adam Wild. How are you?

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I'm awesome, Allan. Awesome. It finally snowed in Toronto, but otherwise it's been very Los Angeles here, so I'm feeling good. I know that you just get to hang out in that all the time, so I'm a little bit jealous.

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Absolutely. All Hello. I have recently been to Minnesota and was in town there for four days. Basically, it became Marc-Andre Flurry Week and had a The Wild did an unbelievable job honoring Flauer for his 1,000 games and 552 career wins, now 554. I just keep racking them up. Second overall in wins among goalies in NHL history. We have an episode right now that I think is going to delve into some of the great unknowns in the sports business that everybody is hungry to hear about and wants more information on. Why don't we jump right into it?

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Let's do it.

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All right. Our guest this week is a great friend of mine and somebody that I work incredibly close with at Octagon. He's been the leader of Octagon's tax division for 15 years. He handles every year over 350 tax returns. Just try to get that through your mind here. He works with elite athletes in the NHL, NBA, NFL, Major League Base, soccer, and all of the individual team sports, some of the leading tennis players in the world, golf, Olympic athletes, and many very high-profile broadcasters. Let's give a big welcome to Sean Packard.

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Let's go.

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How are you, Sean?

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I'm great. How are you?

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Good. Thank you so much for your time and being willing to come on and talk about... There's been a lot of tax issues in the news and the NHL recently, and there's lots of different areas that many people don't have a lot of information about that we'll find fascinating. We're going to do a little a reveal, peek behind the curtain into your world and some of the things that you do to enhance professional athlete lives and keep their financial lives in order, and maybe talk about the few circumstances where some professional athletes have found themselves involved in a lot of chaos and issues with the various tax authorities and how you avoid that. Let's jump right in. I guess my first question is, what makes athlete tax returns and handling professional athletes so unique versus other high net individuals?

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The main issue with professional athletes is that they pay taxes everywhere they travel. If they go to a different state from where their team is located for a road game, they're paying taxes in that state. Sometimes they're paying taxes in the cities. You have cross-border issues going back and forth. The tax treaty tends to handle those. That's the big issue. Most business executives, they'll pay taxes in one state, their home state or where they work. There are commuter tax laws in place to try to tax them when they go elsewhere, but oftentimes, their companies don't comply with the rules. Then the commuter laws, you give a lot of leeway. Sometimes, they don't get taxed unless they're in a state for 30 days. Whereas a professional athlete, day one, they're taxed. The athlete's schedule, their salary is all public information, so it's easy for the states to go in and check the numbers to audit them. Whereas a business executive The state has no real way of knowing if they travel back and forth into their state, but the athlete, they know.

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Sean, is it the player's job and your job to calculate income, or don't the teams do that?

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For team sport players, the teams typically do it, but they're not always 100% accurate. Varying factors come into play there. For example, with With baseball players, 20% of their time is spent at spring training, which is tax-free. But the teams will calculate the duty days based on the beginning of the season to the end of the season. You got this whole chunk of the schedule that they didn't allocate. For hockey players and basketball players, it can be tough because they'll make one salary, one season, another salary, a different salary the next season, and the seasons go overlapping the calendar. It It makes it tough if they play one game and say, New York in the first part of the calendar year, but not the second part, and the salary fluctuates between the two. They do the best they can, but then at the end of the year, we go through and we put together a duty day schedule for everyone, marking down where they were every day of the year, whether they were injured. If they were injured, were they traveling with the team or were they staying back home? Were they suspended for a game?

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Maybe. We take all of that into play, run the numbers, and figure out how much income should be allocated to each state.

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How many players, athletes, do you typically represent in handling their income tax work on an annual basis?

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We do about 350 tax returns. Of those, I would say close to 300 are active players, all the different sports from the team sports to the individual sports. Now, the individual sports, calculating their income is up to the player. It's up to us to calculate how much income they made in each state, for example, a tennis player or a golfer. They have their winnings in a state, but Then they also have their various expenses, their caddies, their coaches, travel expenses, all of that. We go through all the receipts, all the credit card statements, put all of that together and put together an income statement for every state.

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Okay. What do you enjoy most about what you're doing?

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It's interesting work. When I came into this 15 years ago, big sports fan and everything, it's like, this is cool to see a different side of the sports world. Being a tax guy, I always was interested in how the taxes worked, how the money worked. All these years later, it's changed. It's not so much that it's not a sports job where I do taxes. It's a tax job that just happens to be in the sports business. So one of the things that I sit back and look at is just how international the job is, which is cool that I never would have thought that I would ever do when I got into the tax business. Having calls with people all over the world at various times is just... I don't think about it in the moment when I'm doing it, but then when I come back, look at the end of the day, I'm like, Well, I had a call with a guy in Czech Republic and then a guy in and then another guy in the UK all in one day. Like, crazy.

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We work a lot together on our clients, and I work with a lot of players in the Czech Republic and Canadian players and American players and players from Sweden. How do you go about determining the way forward in negotiating contracts hand in hand with the agents and put together a tax strategy going forward for some of your elite players in that regard?

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Let's see. We've had these conversations in the past where there's a free agent player, and he has offer one from one team, offer two from another team, offer three from another team. Let's run the numbers and see what the net is after the taxes from all these deals, because offer one from team one who's in a higher tax jurisdiction may not net out the same amount of money is offer three, which was the lowest offer. That's one of the things we've talked about. We've talked about long-term planning with various guys when they go to Canada, whether they want to do RCA, how much to put into the RCA. Those are really the biggest issues. The free agency is always a fun one just because you're comparing the different numbers to the different places and actually coming down to a net. That's mainly it.

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Okay. So, Sean, you're the guy, and we're about to ruin and destroy and take down a narrative that has existed in the NHL for a long time. This is going to be ground-breaking and earth-shaking to many people listening to this podcast. We all know professional athletes playing in Florida, NHL, playing in Texas, right? Playing in Tennessee, playing in Nashville. They Pay no state income tax. We keep hearing all the time, if you go play in Canada, in Montreal, in Toronto, in Edmonton, you're going to have such a huge tax bite taken out of you that players don't want to go there. Now, I'm not talking about going to Canada or not going to Canada based on the weather, the team, the media attention. I'm talking from strictly an income tax perspective. Can you take an elite player signing with the Toronto Maple leaves, just picking a team out of thin air. Can you do that and get the net tax down to almost where it would be if he played for the Florida Panthers and signed with them? Can you do that?

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It would take some planning, but it could work. Rca, especially, would be the way to do it.

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What's an RCA?

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An RCA is a scheme set up in Canada for high earners to essentially defer some of their salary. Instead of receiving the compensation in the current year, they set it aside and it goes into an account, and they don't pay on it until they pull the money out. That's in its simplest form.

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When they pull it out, if they've followed the rules correctly and are no longer in Canada, at the time that they do pull it out, will pay a flat tax of 25%.

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Correct.

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That is the way over the course of a number of years, a player can end up netting almost the same as what he would net if he played in Florida.

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Correct.

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Okay. You've just destroyed a narrative that exists. I know people right now that are going to be crying in the media because every week as we head into July 1, we hear what a disadvantage the Toronto Maple leaves and the Montreal Canadians have, and the Edmondton Oilers in Vancouver, how they all are at such a terrible disadvantage because of the tax structure in Canada.

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They still seem to sign some solid players, though.

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They do, but the difference is they don't know Sean Packard, and I do, and I'm much better for it. Let's talk a little bit about how compensation is paid to an athlete. We can lean towards NHL because it's what I do.Your audience.Yes. There is base salary and there is signing bonus. There is something called the US Canada Tax Treaty, which differentiates the tax rate for salary versus signing a signing bonus. Help us all out here. Can you explain that?

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A Canadian team signing an American resident, or vice versa, American team signing a Canadian resident, if they pay a signing bonus to the player, if it's a true signing bonus, it is taxed at 15% in the country of residency. An American player signing with a Canadian team would pay 15% in Canada on their signing bonus. And then they could take a foreign tax credit in the US for that amount, but pay US regular rates here. So it would save them a lot of money. Same thing if a Canadian kid were to sign with an American team, the signing bonus would be taxed in the US at 15%, but if he's a resident of Canada, would be tax at the regular rates there.

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Okay. You said some words that trigger something very critical, pure signing bonus. What does that mean?

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A true signing bonus means that it is, one, paid separately from salary, which is almost always the case. The biggest one, two, is non-refundable, and three, does not require additional work by the player. Meaning, once the signing bonus is paid, it is the player's, no matter what he does, he could retire tomorrow, he keeps the money. That's a true signing bonus. That allows the 15% rate.

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Okay. So NHL teams typically like to insert language into the signing bonus clause of NHL contracts, SPC's Standard Player Contracts, which state, for example, if the player voluntarily retires, withhold services, or materially breaches the contract in a prohibited in a limited manner, a pro-rata portion of the signing bonus is reimbursible and refundable back to the club. What does that language do to the tax treatment of the signing bonus?

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It basically nulls the tax treaty. It becomes regular salary, not signing bonus. It's subject to the regular rates, not the 15% reduced rate. Okay.

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And what, to your knowledge, has CRA, Canada Revenue Agency, been doing with large signing bonuses paid to NHL players recently?

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They've been scrutinizing them. We've seen with some of our players who have played in Canada, just long delays before receiving the refunds. They want to look at the contract. They want to look at absolutely everything they can to to change it. So far, we've been successful in all of ours, but we know there are some high-profile players out there that they're going after that are working its way through the court system.

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There's a couple of situations. One, very recently in the province of Ontario, for a player who plays hockey there, who is involved in a revenue court tax challenge to the treatment of his signing bonus? And doesn't it really come down to the language that exists in the standard player contract?

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100 %, because that's what they have to go on. That's the contract that binds the team and the player. So CRA is going to look at that to see what are the obligations for each party. And if the obligation is to perform services after receiving the signing bonus, They're going to have a hard time.

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Okay. Adam, you've been sitting there very patiently, and I know you're loaded with questions.

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I am. I wondered this because my mom's from Pittsburgh originally, She's an American citizen. I have the ability to become a dual citizen at any point. And there was a point in my radio career where I was like, maybe I should go to the States. I started to put together the lists that you have to together. You have to have references. You have to have proof that your family member actually live there, even if they are a citizen. And one thing that they brought up with me that I've always wondered is the difference between American and Canadian tax in terms of empire tax. So the way I understand it, and Sean, correct me if I'm wrong, empire tax is something the United States and one other country in Africa has. Whereas if you're an American citizen and you work anywhere in the world, you are subject to the IRS looking at your income tax and saying, You owe us on this. If you're in Canada and you work somewhere else, you only have to pay income tax where you live. So if I had gone through and gotten my American citizenship, which I have not yet done, I would have to file in both countries, and I would have to prove that my income tax level was higher in Canada than it would be in the States.

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And if it wasn't, I would have to pay a differentiation tax on that. Is that all true?

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Yes.

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How does that a impact American players coming to Canada?

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The taxes in Canada tend to be higher than in the US. So their foreign tax credit helps them out. But when they're in Canada, if they don't establish residency in Canada, we can allocate the days that they're on the road in the US out of Canada. They only pay taxes in Canada on the day as they're performing services in Canada, the rest of it gets pulled out and is not subject to Canadian taxes. That ends up saving them some money. The issue that you can run across is at the state level in the US, if they're a resident of a state with an income tax and they go play in Canada, they only get the foreign tax credit on their federal return, not on the state return in most states. For example, I looked at Kawhi Leonard years ago when he was a free agent and looking potentially to resign with Toronto. He's a resident of California, and California doesn't give a foreign tax credit, so he would have been paying, had he stayed in Toronto, the Canadian tax rates plus the California tax rate. So his income tax for the days he's in Canada would have approached 68%, which would have been brutal.

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Wow.

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That's incredible.

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Now, that is Alan, Sean, that's a definitive disadvantage for a Canadian team, is it not?

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For sure, yes.

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But I would make one point here that's very important. The NBA CBA has prohibited the use of RCAs for their players. So players playing for the Toronto Raptors cannot use RCA's, the Toronto Maple leaves, and there was no prohibition on using them in the NHL CBA. Any player playing in Canada making over a certain amount of money, even though it's not required to make a certain amount of money, it has to make sense because there are costs and fees associated with setting up an RCA. You don't want your salary has to be at a certain level to benefit from the tax structure of the RCA, using it could potentially save you millions and millions of dollars in taxes over the course of a career of a player playing in Canada.

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I guess, Mike, follow up to that, gentlemen, and this is a question for both of you. Fans especially Canadian fans, not knowing what we know about RCA's, because why would that factor into our lives? We make normal income, most of us, not high income earners, just not something that would come across our desk or we would even worry about. Most of us, we get our T4s in Canada. We hand it in with any educational or childcare credits, and maybe we get a few hundred bucks back at the end of the year. Is it time for the league to consider salary caps based based on what local taxes are. What I mean by that is, would you think it's a fairer system? I understand the NBA is a bit of a different animal because the RCA's are prohibited. Is it not more fair, Alan and Sean, if we're going to have these salary caps, to have them be a net salary cap, where players net out the same based on whatever jurisdiction they're playing in. And I understand they're going to play 41 games on the road, and not everything could be 100 % fair. But it does seem a little bit like if there's not a chance, Kawhi Leonard would stay in Toronto, 68 % income tax.

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That's outrageous. That's crazy. Nobody would say yes to that. What do you guys think about that particular situation.

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Adam, are you asking me to endorse in any way a salary cap? Are you actually asking to endorse any a restriction on player salaries other than their pure fair market value?

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I would never ask that. I would just say, if it's a system we have to have, is there not a better way?

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Is that fair? Okay, you could put that over to Sean.

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Okay, Sean? Sean, would you agree that it would be fairer based on local taxes, an adjustable cap?

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Absolutely. Yeah. Now, Kawhi's case was an interesting one just because of the state in which he was a resident. Say, had he been a resident of Texas, he'd been just paying the regular Ontario rates for his time up there. But yeah, going back to your question, if there has to be a cap, then I think it would make sense to adjust it. Now, you'll have the teams in the no-tax states kicking up a fuss about it, teams in low-tax states doing the same. It's like, Oh, why Are we going to do everything just to help a few teams? What do we get out of it? It makes sense, but getting there is the hard part.

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You know what, Sean?

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Wouldn't it just be easier to get rid of it then, Alan?

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Absolutely.

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There we go. That's what I want to hear. That's what I want to hear. Sean, recently, there's been a contract that made a lot of news here in California and around the sports world, there was this monster deal to Shohaia O'Tani with some massive contract deferrals. Can you explain the structure of that deal and why you think it was structured in that manner?

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Sure. The way they structured it is he's going to get paid a small salary for the duration of time he's playing for the Dodgers. After that time, he has a huge sum of deferred money that is deferred each season that will be paid out over a 10-year period once his contract is up. The reason why they put 10 years for the payout of the deferral is because under US law, if substantially equal payments are paid out as deferred income over a period of at least 10 years, it is only taxed in your home state when you receive it, not where you earn it. So essentially what they're doing is setting up a scheme to where he can avoid California's 13.3% tax on substantially all of his income other than the small amount he takes a salary each year, and that will get tax at the end of the contract.

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Do you assume you'll be moving or set up a residency after baseball in a non-tax state, or would he depart the country and then deal with Japanese tax law?

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I would assume he's going back to Japan. So he'll save the tax in California, but Japan's highest tax rate is 45% compared to 37% right now in the US. So he's not saving at the federal level, but he's saving at the state level. If you add the state to the federal, he's still saving a decent amount of money.Wow.Wow..

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That's amazing. Yeah. But he would still have to declare and pay any marketing deals every year as he goes along. I assume he's got very significant endorsement income That would be subject to California every year of the deal, or are there ways to get around that?

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Typically, endorsement income is taxed in your home state. A guy like Ohtani, he would typically meet the substantial presence test. He's in the US over 183 days. But because spring training is in Arizona and they play so many road games. He's not in California that much, not enough to establish residency. So he can avoid paying state taxes on his endorsement income if he never establishes residency in California.

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Wow. Okay. So California wouldn't say, Hey, you play for the LA Dodgers, and the LA Dodgers are paying you your salary. We want California tax on everything you earn, and we're going to consider you a resident?

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No. He'd have to meet the requirements. It sounds crazy talking about California, but fairly liberal residency requirements. They go both ways, though. If you're in the state temporarily, and they'll say temporarily can be a five, six, seven-year contract, but if you're only in the state for your contract and then you weren't there before and you plan to go home afterwards, you're there temporarily. If he doesn't set up really strong ties to California, so if he shows up at spring training, goes to California when spring training is over, and then flies home to Japan when the season is over, he has an established residency in California. He's just there temporarily for a job.

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Does it matter whether he buys a house in California or rents?

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If he rents just for the season, that would make it even stronger that he's not a a California resident. If he buys a house in California, it would add a tie. But if he has a house in Japan as well that he's going back to, and he's only using the California house when he's in town for the season, he could still have closer ties to Japan and not establish in California. Wow.

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Guys, I want to ask you about LLLCs or your personal... Like a personal business. I know that, or at least I'm under the impression, and you could correct me on this if I'm wrong, that a player cannot sign with an NHL team or really any major league team as a corporation. A corporation that renders services. For instance, I've got several businesses. One of them is what I do on my Instagram influencing. One of them is what I do for my job, and let's say I'm also employed. The employment income is taxed at a different rate than the LLC or Corporation income. When you sign with a team, Alan, can you sign as a Corporation or do you have to sign directly as a player employee?

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It's funny. I had an opportunity to sit in an agent's office who was very active representing NHL players in the 1970s. I was looking at contracts that were executed in 1974, in in 1978, with some pretty big NHL players at some ridiculously low salaries compared to where we are in the world today. But they were all done in the name of corporations. The player's name, enterprises Inc, the players' name, Corp. They were all personal services companies that were set up, and it was the players' personal services Corp that actually executed the contract with the NHL Club. That is and has been banned in the NHL for a long time. I have no idea, actually don't know, Sean, what the tax treatment would even be on that now and whether there would be a tax advantage for players to be able to do that. But it actually says in the NBA, in the NHL-CBA, that players cannot contract with a club through a personal services contract. It's all the individual. What do you think, Sean?

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Makes sense. It would complicate things a lot on the tax side. You would still have the state rules because I'm sure the states would look past the corporation. They would say the corporation is doing business in the state by the player being there performing under that contract. The The businesses would register in the states. State corporate laws are different than individual laws, so they may have to pay registration fees, annual report fees. The compliance would be a nightmare. The tax side, I don't think would be all that beneficial. I'm sure some people on huge contracts could find little ways to do it. But if you were to do it as in the US, a corporation, and then the income would go in, pay at the corporate level, and then pay dividends, you're still netting out the same income tax rate. Now, what you could do at the corporate level that you couldn't do at the individual level is deduct your agent fees, deduct your union dues. Up until about 2018, in the US, you could deduct agent fees, union dues, training expenses, all of that. If under a corporate structure, theoretically, Technically, you still could because as a corporation, you can.

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It's no longer an unreimbursed employee business expense. That would be a way to save some money. Like I said, unless you're talking about huge contracts with all the compliance issues and everything, I don't think the savings would be huge, but it might be something.

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What about endorsements? Let's say Pepsi comes in, and you're going to have to imagine hard that I'm a fantastic athlete and I work for Alan. Or actually, Alan It works for me in this scenario. It's scary. Alan comes to me and goes, Adam, we got you Pepsi. This is going to be crazy. And Pepsi is going to pay you a million dollars. Would it make sense for me to run that through a personal corporation at that point because there's no NHL Escrow? And then I could go and write off all the things, like the training and all that stuff that I couldn't through the team. Does that make sense?

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In the US, We have loan out corporations, which are not C-corporations, but S-corporations. Guys who are in that situation where they make a whole lot of endorsement income, millions of dollars, we'll set up those as corporations. Irs requires you to pay a reasonable salary. We run some numbers and come up with what we believe is a reasonable salary to pay them so that they're paying a reasonable amount there. The tax savings comes not from different income tax levels because these S-corporations flow through to the personal return and are still taxed there. Where it comes is from the difference between the amount you pay a salary and the amount of net income there is. You're saving roughly about 3% your self-employment tax there. You have to, again, do a cost-benefit analysis. You're You're filing a separate tax return. You're setting up payroll, so there's fees involved there. Annual reports that you have to file with the state. What is our break-even point to where we're actually saving some money? There are people out there that we work with where they're saving quite a bit of money by going through the corporate structure for their endorsement income.

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Wow. Okay. You know what? It's really complicated to get paid as an athlete, isn't it? It's just unbelievable. There was something about... And Alan, you would know something about this because Flauer would have been directly affected by it. And we're not going to dive into his personal taxes. But I know that there was a city tax in Pittsburgh work, if I'm not mistaken, on athletes that were traveling through. I believe it was just athletes that were traveling through. And that was challenged. And I believe that law has been struck down. Now there is a whole, I think it's 10 years of going back and going who was overcharged and then paying that money out. Sean, for a guy like you, that must be a nightmare because you're going to have to apply to the city for that.

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So we've been working on this one for years. Adam brought up something that's a really sore subject for us. The law firm that has been working with the Players Association on this, you A fantastic group of people, really smart people. They got out ahead of it, and we're notifying all the Players Associations, Hey, I want to let you know we're doing this. In order to get the money back, you're going to have to claim You're going to have to file provisional refund claims. Up until right here is where you can file it and still be on time. Let's get as many of these filed as we can. What we did is we put together spreadsheets of, Okay, this guy was living here, played in Pittsburgh, but he was with some other team. This was the amount withheld. This is the amount of income he made during the year. And send it all to them. They filled out the refund claims and put it all together. But Pittsburgh was very careful not to call their fee a tax. They called it a fee, and that was their argument was that, no, they're paying a fee to use the facilities.

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They called it a usage fee. But they They only charged entertainers. They only charged professional athletes. When the professional athletes were charged, it was based on 3% of their salary times the ratio of games in Pittsburgh divided by total games played. The first issue was the fact that they were doing it on a games-played basis. For example, your NFL players who play a grand total of 20 games, they had back then four preseason and 16 regular-season games, the Steelers players would be taxed at that 3% rate on half of their income. A player from another team who just happens to come play in Pittsburgh would be taxed on one-twentieth of his income would be taxed at 3% instead of looking at all the duty days. So that was issue number one. Issue number two was the argument that they made of this was a de facto tax. It was really a tax. And Pittsburgh said, No, it was just a fee. And Pittsburgh lost.

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They lost big time.

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But it's going to take years to get that all set right, is it not?

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For sure. Yeah, they've been added a few years already. At the point now, they won in the Pennsylvania Court of Appeals. And so Pittsburgh's last chance is to try to appeal to the state Supreme Court. If they do that, then it'll play out for a little while longer where they'll probably lose. Or if they don't appeal to the Supreme Court, it'll be done, and we'll just go from there.

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Some of those potential refunds, if that's the right word, are huge amounts of money that players are sitting there waiting to possibly get back, particularly the players who played many years for a club based in Pittsburgh. We're talking huge, huge money over 8, 9, 10 years. Sean, let me ask you this. You've represented in doing the tax work and filings of some of the biggest superstars in the NBA, some of the biggest superstars in the NHL, same with Major League Baseball, same with Olympic athletes, tennis players, golfers. What was the most complicated tax return for an athlete you've ever done?

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I got... They vary. I have a current I have a few current NBA players who are very complicated returns because more money, more problems, right? There's just various different investments, all of that. The ones that always complicated are when players go mid-year from an American team to a Canadian team or vice versa. It's worse on my end when they go from American to Canadian, because what we have to do in breaking down that return, especially if people who have been well-established here, have a lot of investments and all of that, we have to break down, okay, what was earned in the US up until the date they left, and then what was their income up in Canada after they left. Because the investment income is taxed differently, but Then, breaking down all the state tax returns for the portion of time they were in the US and the portion of time they were in Canada, because teams will withhold in a lot of states, but some states follow the treaty, so we want to get some of that money back. Then, when they're considered a dual status resident, meaning a US resident for part of the year and Canadian resident for the other part of the year, we have to file that return by paper.

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Alan has seen me send him pictures every so often of a ruler next to a stack of paper where I'm saying, Hey, this is this guy's tax return.

[00:43:21]

And the paper is stacked a foot high. Wow. What's the What's the biggest return you filed? It was probably over a thousand pages?

[00:43:36]

Oh, easy. When you go with the federal in all the states, and if there are a bunch of investment income, stock transactions and all that, then we have to break down, it can be huge. I love that you just threw easy out there.

[00:43:50]

Easy. Oh, a thousand pages easy.

[00:43:52]

That's wild, Sean.

[00:43:56]

Adam, NHL Trade Deadline is coming up this year, March eighth, and you've got live shows on TSN, on Sportsnet, NHL Network, ESPN. Usually the day after Trade Deadline is when I get a call from Sean, almost in tears, saying, This player got traded. I'm like, Yep. He goes, Oh, my God. All the issues Sean just talked about, no one ever hears about that part the business. Nobody even considers that part of the business. You have everybody up on TSN and Sportsnet talking about the merits of the trade and the return and everything else. Sean and I are commiserating the next day over how complicated it is now going to be to get the tax return done.

[00:44:51]

Trade deadline is one of those things where it's exciting, but I also dread it, too. I'm constantly updating my Twitter feed. They're hoping that guys guys don't get traded, especially cross-border.

[00:45:02]

You're hoping to ban the trade deadline, Sean? If it was up to you, no more trade deadline. No more trade.

[00:45:09]

I had a couple of NBA players traded at the last minute of the last hour or so of the trade deadline there. I was like, All right, we made it through. Then I hear this guy and this guy got traded. Like, Oh, no.

[00:45:25]

That's wild. Honestly, Sean, and I'm sure you're used to hearing this, there isn't a day of my life where I've ever considered the tax implications of trade deadlines. Not till today.

[00:45:36]

Why would you? Yeah.

[00:45:38]

Wow.

[00:45:39]

Or the operation of the Canada US Tax Treaty.

[00:45:43]

Yeah, no kidding. Well, listen, I barely... I know as much as I need to know about the Canadian Revenue Agency, right? The CRA. But knowing two tax codes federally and then state and provincial taxes, and I'm sure you have to look a lot of this stuff up, but after a few years, you probably... California is this rate, and New York is this rate, and Massachusetts is this rate, and Florida is this rate, whatever. I'm sure you probably have some of the best cross-border tax knowledge in the entire world. Where else would you know this? Why would you need to?

[00:46:20]

I don't know. I don't know. Luckily, I have some tax partners that I work with, various countries around the world that help me out, which is great.

[00:46:29]

Yeah, no You should know that Sean has also written many articles for publications like Forbes magazine on the tax implications of certain things that happen in the sports world as it affects athletes. Sean, you're a very humble guy, but I can tell you that one of the great benefits of being at Octagon all these years was having you as this incredible resource and partner in negotiating contracts and in understanding some of the subtle issues that even as a lawyer, I was never exposed to in law school and didn't really appreciate until we started working together. In issues like signing bonus versus salary and and when players get traded from the US to Canada or from Canada to the US, really what you do, your knowledge and your ability to explain it in a way that layman can understand is second to none. We're all very fortunate to know you and work with you, and we've worked very closely over the years. I can't tell you how much respect I have for you in the amazing job that you do.

[00:47:57]

Thanks. You're way too kind.

[00:47:58]

Thank All that math, you're so relaxed about it, too. That wouldn't be me.

[00:48:06]

At this point, what are you going to do?

[00:48:11]

Do you have any final, really good stories about some of the things that you've experienced in your professional career on the athlete side? Give us one of your best or favorite.

[00:48:33]

I don't know. It's hard. It's just little things, I guess. One of your long-time clients, Ruslan Fedratenko, was in the DC area, so I'm a Caps fan. Whether that guy was playing with Pittsburgh or New York, he would always kill the Caps in the playoffs. He'd score big goals left and right. As long as I work for him, I would always like, Dude, did you have to do that? That's fun to do with him. It's fun watching guys win championships and accomplish big personal goals and being able to shoot and fire them in email and be like, Hey, that's awesome. Well done. Another fun experience that I had was this past year at the draft. Adams, you know we work with Mike Lut. Who won the Ted Lindsay Award back... Jeez, was it '79 or '81? Anyways, me and one of my coworkers were walking past where they had the display of all the trophies, and I was like, Hey, I think the Ted Lindsay is in there. It was right on the side. I'm like, I got to get a picture with this thing. Let's find Mike on here. I'm looking down, and all of a sudden, I hear this guy yelling like, Hey, you can't be there.

[00:49:54]

I'm like, What? I'm just looking. He's like, You can't lean over there. My coworker, without hesitation, goes, You know his dad's name's on this trophy? He wants to get a picture for his dad. Another security lady is like, Really? He goes, Yeah, it's his dad right there. Okay. He took the picture, sent it to Mike, and went and told him the story, and Mike about lost it. He's like, You're dead. I'm not old enough to be your dad.

[00:50:22]

By the way, Mike Leut, an all-time funny guy. What a storyteller that guy is.

[00:50:29]

Yes. Yeah. And a great goalie, too.

[00:50:33]

A great goalie. For those that don't know, he's the co-managing director of Octagon Hockey with me, and we've been working real closely together since 2004. Brilliant guy, and it's surreal working as closely with him as I do, having gone to the Montreal Forum as a much younger person, watching him play with the Hartford Whalers, and before that, the St. Louis Blues. Sean, you experience a little bit of that as well. It's like, wow, people you've watched play, one day are your coworkers and colleagues, which is pretty cool. Bobby Witt in the baseball division with Bobby Witt Jr. Bobby Witt with Octagon Base, and Bobby Witt Jr. Is a client. I mean, that's pretty surreal for a lot of people who are also fans growing up. And then you're working in the business, working with people who you watched play. I vividly recall going to games and watching people playing in games that I'm routinely dealing with, either on the general or the President side or the president side or the coach side. It's one of the fringe benefits of the job. Adam, anything else Well, you know what?

[00:52:16]

I never thought that I would get the chance to talk Empire tax with anybody. So just that alone has been a real pleasure. I remember the tax lawyer from the States I was talking to on the phone, she's like, I know this is This is incredibly boring, but I'm going to tell you about it anyway. I'm glad that I was able to put it to some use, Sean. Thank you for making time for us. This has been incredibly... I mean, we've learned so much, and you were a saint because you seem not to worry about that job. If I had to worry about where a player was every day of the year, trying to calculate the tax based on that, let's just say it wouldn't be the job for me.

[00:52:57]

You're talking to me on February If we were to talk on April first, April second, I might be in a different mood.

[00:53:04]

Fair enough.

[00:53:07]

Sean, thank you so much for being so generous with your time. You are such a great guy to work with, and I'm really honored you would come on here and share some of your vast knowledge with everybody. I hope people are thinking of us the day after Trade Deadline when we have our call together and commiserate over For at least one or two guys to get moved and everything that we got to get done in that regard. But thank you again. You and what you bring to our lives every day is so appreciated.

[00:53:48]

I appreciate that. It's fun coming on here. I've been listening for a while, so it's good to finally be on.

[00:53:53]

Our apologies on that.

[00:53:55]

No, I didn't mean finally. It was just good to be on.

[00:53:59]

All the best.

[00:54:01]

This has been Agent Provocateur with Alan Walsh and Adam Wild. Follow Alan Walsh on Twitter @Walsh. A. Subscribe wherever you get your podcast by searching Agent Provocateur and hitting the subscribe button, youtube. Com/sdpn.