Tax attorney. 🎰 Gambling · 🌿 Cannabis · 🎥 Creators · 🤝 Nonprofits
New York, NY
Joined October 2011
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You don't get to hold the checkbook and then act like you're the one being robbed.
"You worked every single day to provide for yourself, your family, your loved ones, to send your tax dollars to the state of California, to the federal government to do what? To pay for people that are robbing us blind, that are looting us, pillaging us, plundering us."
White House Deputy Chief of Staff Stephen Miller unloads on alleged fraudsters, accusing them of taking advantage of hardworking Americans who show up every day, provide for their families and pay their taxes.
Miller singles out California and the federal government as he questions where taxpayers' hard-earned money is going.
people want simple tax laws until one of those laws applies to them. then they want a very reasonable exception with fourteen conditions and a retroactive election.
The sportsbook doesn’t have to know who wins the next bet if it knows who is likely to lose over time.
Josh Hamlet retweeted
Breaking: the big tax bill with a provision to repeal the 90% cap on gambling losses was just overwhelmingly voted through, with bipartisan support, to the House Rules Committee. It’s a technical step before it goes to the House floor for a full vote.
The 90% cap on gambling losses would be repealed retroactive to 1/1/26 as part of the Ways & Means tax bill.
Joint Committee on Taxation estimates a negative impact on revenue of $2 billion from ‘27-36 from this repeal.
The ‘27-34 estimate is $1.5 billion, up 33% from its $1.1 billion estimate during same period.
Wonder if this means estimated tax payments from gamblers were higher than anticipated?
Josh Hamlet retweeted
Very pleased to see that my gambling loss tax deduction fix has finally been included in a tax package. I encourage my colleagues to push it through @WaysandMeansGOP this week as quickly as possible.
The IRS spent today telling bettors to stay on licensed books and report everything.
The licensed book sends a W-2G. The offshore book sends nothing. And in 2026 the 90% cap can hand a breakeven player a tax bill on money he never kept.
You cannot run a compliance campaign and a phantom income tax at the same time.
irs.gov/compliance/criminal-…
Most coverage of the 90% gambling loss cap has the target wrong.
Get crushed this year and it doesn't touch you. The loss absorbs the disallowance before it hits your return.
It bites winners and near-breakeven volume players. The ones with the cleanest records.
10 questions on what it changes for you.
claritytaxcounsel.com/indust…
Two guys bet $500 on Spain. One on DraftKings, one on Kalshi. One is a degenerate, one is a trader. Only one gets taxed on money he didn't make.
Last week I testified at the IRS hearing on the 90% gambling loss cap from a beach in Spain. The static everyone heard was the sea. Then the sea hung up on me mid-argument. I have now testified before a federal agency for less time than the average WSOP main event tank.
A week to digest, and here's what sticks. Everyone at that hearing knew the rule taxes money nobody made. Win 500k, lose 500k, owe tax on 50k. Congress knew the math when it wrote the provision. It passed anyway, because gamblers have no defenders in a markup.
And there's no upside to trade against. The projected revenue assumes people keep betting where the IRS can see them, while the former bookie who testified says the money goes offshore and underground where nothing gets reported at all. Follow it through and this rule is an administrative nightmare (matching notices built on phantom numbers), an ethical one (the burden lands entirely on honest reporters), a legal one (an income tax should require income), and a public health one (the players least able to absorb it get pushed to unregulated markets).
Full testimony below, including the part the ocean kept off the record.
@fairplaygov @PokerCPAs @ToddWitteles @repdinatitus @SaraSmartist
Josh Hamlet retweeted
Just got an email re: testifying on the 90% gambling loss deduction issue.
I'm slated to speak third and there is a nice group of people who will also be testifying.
Let's go!!!
Josh Hamlet retweeted
AGA, @RepDinaTitus, @PokerCPAs, @Josh_Hamlet (both are gambling tax pros) & several poker players / gamblers to speak at Friday's IRS tax hearing on the 90% gambling loss deduction cap.
*This IRS panel doesn't have the power to change the rule but hopefully there will be some takeaways from testimony and panel comments to bring to Congress.
Everyone's handicapping the CFTC vs. states showdown at SCOTUS. The part getting less attention: Curtis-Schiff would amend the CEA to reclassify sports event contracts as gambling — meaning even a CFTC win could be legislated away. Congress is the wildcard. Talked to @CasinoBeatsCom about it: casinobeats.com/2026/07/06/c…
Quoted in @MJBizDaily 👇
@Trulieve became the first US cannabis company to list on the @NYSE. Now everyone's asking who's next.
Rescheduling didn't open that door for everyone. Trulieve restructured into a medical-only company with DEA-registered, ring-fenced assets. That's a specific structure, not a new baseline.
The exchanges' bar is federal-law compliance, not schedule classification. Adult-use operators are still on the wrong side of it, reverse split or not.
mjbizdaily.com/news/after-tr…
Unpopular take: this is not a regulator problem, it’s a statutory one. Kalshi keeps winning on CFTC preemption, NAD is a voluntary body with no teeth, and the disclosure regime for prediction markets is something Congress never actually built. This is a vacuum and Kalshi is playing it correctly.
NY taxed a guy for working from home during a lockdown it ordered, and its defense is he could’ve worked “from within New York.” From WHERE?! Everything was closed. The state shut every door in New York and then sent him a bill for not walking through one.
Judges with a New York appellate court questioned whether the state's convenience of the employer rule is rational in its treatment of remote work during the state's COVID-19 restrictions. taxnotes.co/4vlEnfv
