Pittsburgh Sacked

Jock taxes impact nonresident athletes (and others) who perform in out of state venues.  Let’s say you’re in the National Hockey League (NHL), playing for the Vegas Golden Knights.  You play a game in Pittsburgh.  You now owe tax to Pennsylvania and, because Pittsburgh has a nonresident tax on performers, to the city of Pittsburgh.

Pennsylvania law allows a “Second Class City” (yes, Pittsburgh is literally that–but it’s actually defined by Pennsylvania law as a city with a population of more than 250,000 bet less than one million) to impose up to a 3% tax on earnings at sports venues for nonresidents. However, the Pennsylvania Constitution (article VIII, § 1) states, “All taxes shall be uniform, upon the same class of subjects, within the territorial limits of the authority levying the tax.”  Pittsburgh residents pay a 1% earned income tax plus a 2% school district tax; nonresidents pay 1% on income plus a 2% “Facility Fee.”

Three NHL players plus the players associations for the NHL, NFL, and major league baseball sued Pittsburgh.  They won in the lower courts, but Pittsburgh appealed to the Pennsylvania Supreme Court. Yesterday, the court ruled that the 2% Facility Fee is indeed unconstitutional.

The court noted that they had to determine, “…whether there exists ‘some concrete justification’ for treating the relevant taxpayers as members of distinguishable classes.” If the court couldn’t find that, the tax would be unconstitutional.

And that’s what the court found:

Here, the City does not provide concrete reasons that would justify taxing nonresident athletes and entertainers more than resident athletes and entertainers. Instead, the City once again argues that the facility fee “does not impose an unequal tax burden on nonresidents” because it actually equalizes the tax burdens of resident and nonresident performers. Residents who perform at the stadiums are taxed three percent of what they earn (one percent to the City and two percent to the School District), and now—because of the facility fee—nonresidents also pay a three percent tax. The City maintains that a tax which equalizes the burdens between two groups of taxpayers cannot violate the Uniformity Clause. [citations omitted]

When an argument loses at two lower courts, you might think about finding something else as backup for your cause. Pittsburgh didn’t. The result wasn’t good for the Second-Class City:

Because the two percent Pittsburgh School District tax cannot be used to justify the facility fee in our Uniformity Clause analysis, and because the City of Pittsburgh has not supplied a “concrete justification” for treating resident athletes and entertainers differently from nonresident athletes and entertainers, we agree with the lower courts that the facility fee is unconstitutional. [citation omitted]

Pittsburgh will need to repay a lot of athletes, and this is definitely going to put a strain on the Steel City’s finances. It’s also a reminder that uniformity means just that.

 

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About That List of Occupations Eligible for “No Tax on Tips…”

You may have seen a list of occupations that are eligible for the One Big Beautiful Bill’s “No Tax on Tips” provision.  And perhaps your occupation is on that list, and you’re thinking, “Wonderful! My taxable income is going down!”  Perhaps that’s the case, but there’s a chance that won’t be true.

The problem, one noted quickly by Tom Gorczynski (and I agree completely with Tom), is that there are two parts to qualify for this tax break.  First, the occupation must be one where tips were customarily and regularly received prior to 2025.  Second, the occupation must be one which is not a “Specified Service Trade or Business (SSTB).” 

What is an SSTB? The Tax Cuts and Jobs Act (TCJA), the tax bill that passed during the first Trump Administration, allowed for a new deduction (the deduction for Qualified Business Income).  However, certain businesses–called Specified Service Trade or Businesses–had limitations built into this deduction.  Generally, if your business is one based on the reputation or skill of the employee or owner (such as attorneys, tax professionals, and consultants/personal coaches), you’re an SSTB.

If we look at the list published by Treasury, there are numerous SSTB occupations listed.  For example, a tennis coach is clearly an SSTB. Sure, he may have receive tips but the second part of the test will disqualify that coach from receiving this tax benefit.  (Of course, many of the occupations listed are absolutely not SSTBs, such as waiters, bartenders, and gaming dealers.)

I’d love to reclassify my business as a “Self-Enrichment Teacher;” that happens to be one of the professions listed on the list published by Treasury. Clearly, tax professionals help individuals keep more of their money; that’s absolutely self-enrichment.  Unfortunately, changing the name of my business to “Clayton Self-Enrichment LLC” won’t change my profession.  My dream of changing my billings from “Tax Preparation” to “Self-Enrichment Fee” will just not work.

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IRS Closes Cincinnati Lockboxes; New Addresses In Effect Immediately

Last week, the IRS released Publication 3891.  This publication lists out where to mail paper-filed returns and payments for the 2026 tax year.  Currently, Nevadans mail many IRS payments to addresses in Cincinnati, but not anymore.  Spidell reports that the new addresses should be used immediately.  

The major change for residents of Alaska, California, Colorado, Hawaii, Idaho, Kansas, Michigan, Montana, Nebraska, Nevada, Ohio, Oregon, North Dakota, South Dakota, Utah, Washington, and Wyoming is that there are new addresses to mail Forms 1040-V and 1040-ES. (Paper-filed forms 1040 with a payment go to the 1040-V address.)  The new address for residents in these states for Form 1040-V is:

Internal Revenue Service
PO Box 931000
Louisville, KY 40293-1000

The new address for residents of those states for Form 1040-ES is:

Internal Revenue Service
PO Box 931100
Louisville, KY 40293-1100

While the IRS states they will forward mail from the old Cincinnati addresses, I would, if at all possible, use the new address.  The IRS’s ability to deal with correspondence is dreadful, and while penalties will be waived if you can prove you mailed it to the Cincinnati address why deal with that at all! [1]

Even better, if you pay electronically (using IRS Direct Pay, EFTPS, your IRS online account, or having your tax professional have your bank account debited with the filing of your return) you avoid any issue at all.

Other addresses have changed, too, including where to mail extension payments and where to mail business payments.  Those are also noted in Publication 3891.

[1] Remember, to prove you mailed anything timely to the IRS it must go by certified mail.  Yes, it will cost you $5.30, but it’s well worth it.

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I’m Tipsy on Overtime

The IRS issued a press release yesterday:

The Internal Revenue Service today announced that, as part of its phased implementation of the One Big Beautiful Bill Act, there will be no changes to certain information returns or withholding tables for Tax Year 2025 related to the new law.

Key points for TY 2025 relating to OBBBA provisions:

  • Form W-2, existing Forms 1099, and Form 941 and other payroll return forms will remain unchanged for TY 2025.
  • Federal income tax withholding tables will not be updated for these provisions for TY 2025.
  • Employers and payroll providers should continue using current procedures for reporting and withholding.

These decisions are intended to avoid disruptions during the tax filing season and to give the IRS, business and tax professionals enough time to implement the changes effectively.

There’s problem here: Certain tip income and overtime income isn’t subject to tax under the OBBBA.  How am I, a tax professional, to know the total of tips and overtime?  Or that the taxpayer worked in an industry where tipping is ‘normal?’

For tips, there is a box on the W-2: box 7, so that should be straightforward as to the amount paid. As to the industry, well, I’ll have to use my judgment.  But there’s no box on the current W-2 for overtime.  That means either it will need to be listed as an other item in Box 14 (the current ‘catch-all’ box) or we’ll need the final pay statement (aka pay stub) for the year for anyone who earned overtime.

The new OBBBA may be good for many workers, but it absolutely adds complexity to tax preparation.  It will increase the amount of time it takes to prepare a tax return.  Given the OBBBA didn’t (and couldn’t) change the clock–our day still remains 24 hours–and I’m loathe to require my employees to work additional hours (nor do I really want to myself), that means the cost to prepare a 2025 tax return will rise.  And that’s before inflation, demand increase, and the overall shortage of tax preparers is factored into the cost.

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A February 17th Start to Tax Filing Next Year?

Yes, we’re looking at a late start to Tax Season next year.  New IRS Commissioner Billy Long said at the recent National Association of Enrolled Agents (NAEA) annual meeting (per a friend’s email–I did not attend) that the IRS expects next year’s tax season to begin on February 16th.  That’s President’s Day, so a February 17th beginning looks likely.

I’m not yet ready to call next year’s tax filing another “Tax Season From Hell,” but it sure looks that way to me.  We have a lot of tax law changes, an even more compressed filing season than usual, and the IRS will be understaffed.  It doesn’t look good (though that’s six months from now).

I’ve learned that version 0 of tax software is to be avoided.  Tax software is quite complex, and there’s an interaction between the software companies and the IRS (of course).  If the IRS isn’t ready to process returns, many forms from the software companies won’t be ready.  Typically, some forms aren’t ready until one month after the first day the IRS accepts returns.  That means many returns won’t be able to be filed until late March.

What does this mean for taxpayers?  Lots and lots of extensions for 2025 tax returns filed in 2026.  Higher costs for tax preparation next year are also likely.  There are only so many hours in the day, and if tax season gets compressed–and that appears a near certainty–it’s another cap on supply.  If supply goes down, price goes up; that’s basic economics.

Additionally, the IRS uses old–let’s be honest, it’s ancient–technology.  We’re talking computers that are older than I am (dating to 1959).  Everything I’m seeing looks like a lot of storm clouds on the horizon.  That storm may miss us, but it sure doesn’t look that way.

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New Portal Delayed Until Next Week

Our newsletter (which has gone out) notes that you should have received an announcement on our new web portal.  You haven’t.  The current (old) portal is still active; the new portal will be released next week as there was a minor delay.

(We have to submit the newsletter for publication a few days ahead of its release, and that was the cause of the issue.)

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The Real Winners of the 2025 World Series of Poker: Zero Is the Best Number

This year’s main event of the World Series of Poker (WSOP) attracted 9,735 entrants each of whom paid $10,000 attempting to become the World Champion. This wasn’t a record (last year’s field had 10,112), but it was still the third largest. The winner would receive a cool $10 million. How much of it did he actually get to keep (before taxes)?

One important 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 (and/or “swap” action with other entrants). It is quite likely that most (if not all) of the winners were backed (or had swaps) and will, in the end, only enjoy a portion of their winnings. I ignore backing and swaps in this analysis (because the full details are rarely publicized). Now, on to the winners.

Congratulations to “The Grinder,” Michael Mizrachi of Miramar, Florida (near Miami). Not only did he thoroughly dominate the final table, he had earlier won what is probably the most difficult event at the WSOP, the $50,000 Poker Player’s Championship. That event features almost all professional poker players proficient in multiple poker variants. (Mr. Mizrachi has now won the Poker Player’s Championship four times!) Yesterday, on the final hand he made a flush with his ten-three of clubs; his opponent, John Wasnock, had two pair and did not improve on the final card. As a resident of Florida, he doesn’t have to worry about state income tax (the first of many instances of zero being great in tax). He does have to pay both US income tax and self-employment tax; I estimate he will pay $3,967,255 leaving him with $6,032,745.

In second place is John Wasnock, an investment consultant from North Bend, Washington. Per the Hendon Mob database, he had previously earned just $143,643 in poker tournaments; he definitely added to that with his $6,000,000 second place prize. Washington state doesn’t have an income tax; he’s also not a professional gambler so he doesn’t have to deal with self-employment tax on his winnings. I estimate he will pay $2,209,894 in tax (and keep $3,790,106).

Braxton Dunaway of Midland, Texas finished third. He works in the petroleum industry and also happens to be an accomplished amateur poker player. Texas is another state which doesn’t have an income tax. Like Mr. Wasnock, he also avoids self-employment tax. I estimate he’ll keep $2,524,527 of his $4 million third place prize (paying $1,475,473 in tax).

Kenny Hallaert, originally from Belgium but now residing in London, England, finished in fourth place. Mr. Hallaert is a well-know player and poker tournament director; he’s also known for annually putting together a spreadsheet of all the poker tournaments running in Las Vegas during the summer. This is the second time he’s made the final table of the Main Event (he finished sixth in 2016). This year he earned $3 million. The US tax treaty with the United Kingdom exempts gambling winnings (so the IRS gets nothing). Additionally, the United Kingdom doesn’t tax gambling winnings. It’s always good when your after-tax income is equal to your pre-tax income.

Luka Bojovic of Vienna, Austria (originally from Serbia) came in fifth place for $2,400,000. The professional poker player (who is also a doctor) was nearly completely “card-dead” on Tuesday (during the first day of the final table of the Main Event) and did an excellent job to finish fifth. The US-Austria Tax Treaty also exempts gambling winnings, and Austria is another country that doesn’t tax gambling. Thus, Mr. Bojovic is another individual who gets to keep all of his winnings.

Adam Hendrix, a professional poker player residing here in Las Vegas, ended in sixth place earning $1,900,000. An accomplished professional, his Main Event finish moved his career earnings over $10 million. I estimate that Mr. Hendrix will owe $698,000 in tax (just under 37%).

Leo Margets was the first woman to make the final table in 30 years (the last was Barbara Enright who finished fifth in 1995). Most of the poker world was hoping that she could find a way to win; however, the poker professional from Barcelona, Spain fell in a hand against Kenny Hallaert. Ms. Margets had ace-ten against Mr. Hallaert’s pair of sixes. On the turn (the fourth board card), Ms. Margets paired her ace but it gave Mr. Hallaert a flush draw. The river card (the final card) gave Mr. Hallaert the flush, and ended Ms. Margets’ run. She did earn $1,500,000 and the IRS gets none of it (the US-Spain tax treaty exempts gambling). However, Spain is not a low-tax country; Ms. Margets is lookin gat losing 47% of her winnings to tax ($705,000) and will keep an estimated $795,000.

Jarod Minghini, a professional poker player from Lake Tahoe, Nevada, ended up in eighth place earning $1,250,000 before taxes. This is, by far, Mr. Minghini’s largest cash of his career. Like the other American professional gamblers, he does have to pay self-employment tax along with income tax. However, like Mr. Hendrix, Mr. Minghini resides in Nevada, another state with no income tax. I estimate he will pay 38.52% of his winnings in tax ($481,553) for an after-tax prize of $768,447.

Daehyung Lee is the first South Korean to make the WSOP Main Event final table; he finished ninth for $1 million. The US-South Korea Tax Treaty does not cover gambling; thus, $300,000 of his winnings will be withheld by the IRS. South Korea has marginal tax rates from 6% to 45%, plus residents must pay a 10% local tax (a surtax). I estimate Mr. Lee will lose $517,212 (over half his winnings) in tax. His tax in Korea will be $517,212 but he should be able to claim a foreign tax credit on his US withholding of $300,000.

Here’s a table summarizing the tax bite:

Amount won at Final Table $31,250,000
Tax to IRS 9,132,175
Tax to Agencia Tributeria (Spain) $705,000
Tax to National Tax Service (S. Korea) $217,212
Total Tax $10,054,387

That means 32.38% of the winnings at the final table goes toward taxes.

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

Winner Before-Tax Prize After-Tax Prize
1. Michael Mizrachi $10,000,000 $6,032,745
2. John Wasnock $6,000,000 $3,790,106
4. Kenny Hallaert $3,000,000 $3,000,000
3. Braxton Dunaway $4,000,000 $2,524,527
5. Luka Bojovic $2,400,000 $2,400,000
6. Adam Hendrix $1,900,000 $1,202,000
7. Leo Margets $1,500,000 $795,000
8. Jarod Minghini $1,250,000 $768,447
9. Daehyung Lee $1,000,000 $482,788
Totals $31,050,000 $20,995,613

Once again, a player ended up placing higher than his actual finish based on after-tax results. This year, Mr. Hallaert finished in third place based on after-tax winnings; additionally, Mr. Bojovic just missed finishing in fourth place based on after-tax income. Zero percent tax rates absolutely have influenced where both individuals now reside.

One loser this year were state income tax agencies. None of the Americans making the final table owe state income tax because they all reside in a state with no income tax (Florida, Washington, Texas, and Nevada). Yes, Washington state has every other tax known to man (besides an income tax) and both Florida and Texas have relatively high property tax rates. Still, zero percent is quite desirable in tax.

This was another year where the Internal Revenue Service missed out on earning more at the final table than first place with just $9,132,175. Still, you can’t say that the IRS didn’t do poorly because the house always wins.

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Did the W-2G Threshold for Slots Get Increased in the One Big Beautiful Bill?

I’ve seen reports online that the threshold for issuance of W-2Gs was increased in the One Big Beautiful Bill (OBBB) to $2,000 from $600.  Is that true?

First, the threshold for issuance of many 1099s was increased by the OBBB to $2,000 from $600 beginning in 2026.  That’s in §70433 of the OBBB (which amends §6041(a) of the Tax Code).  Thus, next year (not for 2025) there will be fewer 1099s issued.

What I think some commentators read (and wrongly interpreted) is §70433(d) of the OBBB:

(d) APPLICATION TO BACKUP WITHHOLDING.—Section 3406(b)(6) is amended—
(1) by striking ‘‘$600’’ in subparagraph (A) and inserting ‘‘the dollar amount in effect for such calendar year under section 6041(a)’’, and
(2) by striking ‘‘ONLY WHERE AGGREGATE FOR CALENDAR YEAR IS $600 OR MORE’’ in the heading and inserting “ONLY WHERE IN EXCESS OF THRESHOLD.”

The issuance of W-2Gs is governed by §3402(q) of the Tax Code (and related regulations); that was not changed in the OBBB.  Thus, beginning in 2026 a W-2G must still be issued at $1,200 for a slot win but backup withholding will not begin until $2,000!

Now, it’s possible Congress meant for both limits to increase.  Typically a “technical corrections” bill is proposed.  This is usually bipartisan, and fixes “oops” items.  However, given how polarized Congress is I have my doubts of such a measure passing this year.  And it might be that Congress intended this to be exactly as it is.

Finally, it is possible the IRS will interpret this law change to mean the W-2G threshold is increased to $2,000.  That would be welcome by almost everyone but I would not hold my breath waiting for that interpretation.

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Senate Version of Big, Beautiful Bill Is Bigly Ugly Towards Gambling

The extension to the Tax Cuts and Jobs Act (TCJA) is now in the Senate as the “Big, Beautiful Bill.”  The Senate version will likely receive a final vote today (and pass); however, it is quite different in certain areas from the House bill (that earlier passed that chamber).  And it is really ugly (or to use one of President Trump’s phrases, bigly ugly) towards gambling.

The Senate version would permanently change Internal Revenue Code Section 165(d):

  • Limit gambling losses to 90% of gambling winnings Limit gambling losses to 90% of the gambling losses incurred, and
  • For professional gamblers, the total of losses and business expenses could not exceed are reduced to 90% of gambling winnings losses and business expenses incurred.

Consider Joe, an amateur gambler who comes to Las Vegas once a year.  He breaks exactly even, with $100,000 of gambling winnings (all on W-2Gs) and $100,000 of gambling losses.  If he doesn’t keep a session log he’s going to owe tax on $10,000 of income.

Or consider Larry, a professional gambler, with $500,000 of gambling winnings on the poker circuit, but $440,000 of losses and $50,000 of ordinary and necessary business expenses; he’ll have to pay tax on $50,000 $59,000 of income rather than his $10,000 of net income.

UPDATE: This isn’t as bad as I initially reported (but it is bad–especially for professional gamblers).  Most amateur gamblers lose.  Let’s consider Lisa, an amateur gambler with $100,000 of gambling winnings. If she has $111,111 of gambling losses she will be able to fully offset her gambling winnings with losses.

However, many professional gamblers report winnings, and their total of business expenses and losses will be reduced to 90% of the actual number.  In the example above for Larry, I initially had his taxable gambling income (under the Senate bill) as $50,000.  It is $59,000 as his $490,000 of losses and business expenses will be limited to $441,000.

I do need to point out that these provisions are not in the House version (the House version simply extends the current TCJA limitations on business expenses causing a loss for professional gamblers).  This is one of many areas where the two versions are not the same and will need to be ironed out (likely in a conference committee).

There are two inescapable conclusions if the Senate version becomes law.  First, keeping a gambling log will be essential: If Joe had $100,000 of wins and $100,000 losses in the same session he would have $0 of gambling winnings.  Second, this would be another big negative towards gambling and would definitely hurt tourism in areas like Nevada.

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Missouri Joins New Jersey in the Hall of Shame for Encouraging Identity Theft

Earlier this year the New Jersey Division of Taxation asked one of my clients to email documentation–including his social security number.  We refused.  As New Jersey’s own advice notes, emailing personally confidential information like a social security number is a bad idea.

Enter the Missouri Department of Revenue.  A client moved from Missouri a few years ago, and began filing returns in his new state (as he should); he filed a part-year return for his final year in Missouri.  Missouri thought he remained a resident for the following year and asked our client to email his unmasked tax return to the state (he had mailed a copy via certified mail–which they did receive).  We’re not going to email it.  As the Missouri Department of Revenue correctly notes,

Only use a secure connection on the Internet when sending credit card numbers or other personal information. [emphasis added]

The Department of Revenue is absolutely correct about this: emailing personally identifiable information like a social security number should never be done.  Yes, an email attachment is easier to work with than having to scan a paper return.  But I will never email anything containing a social security number and I hope my clients won’t.

We are going to fax the return.  Faxing, because it is analog, is generally secure.  Yes, Missouri is going to again have to convert paper into a pdf, but unless they offer my client a secure upload facility that’s their problem.

 

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