Ever since the “Big Beautiful Bill” was signed into law in July, and Russel Fox appeared on Gambling with an Edge explaining that I’d have to pay income tax on 10% of my W-2Gs whether I won or lost during the year, I knew I’d have to quit gambling come January 1, 2026.
I received more than $6 million in W-2Gs both this year and last. In 2025, I made money but would be minus after this extra tax. In 2024, I lost quite a bit of money gambling and would still have this big tax bite under the new law. No thanks.
Since July, I’ve at least mentioned this in numerous blogs, so this decision is no surprise to any of my regular readers.
While I was in Cherokee in early December this year, my gambling partner was a fly-on-the-wall during a Zoom call with Gary Kondler, who works for the Kondler and Associates CPA firm, which specializes in taxes for gamblers. It is Kondler’s belief that if gamblers use the session method of itemizing their wins and losses, mentioned in Shollenberger vs Commissioner, the BBB tax bill isn’t such a big deal. Yes, the tax bite will increase — but not outrageously so. Your W-2Gs, whose total must still be listed on your tax form, are not relevant in how much you have to pay.
Tell me more!
This is something I want very much to be true — and there are a variety of proverbs that warn you to be very careful if something seems too good to be true. I tried to do as much “due diligence” as I could.
It turns out that Gary’s father, Ray Kondler, was a guest on Gambling with an Edge in 2013. This was when GWAE was an hour-long radio show on Thursday nights rather than a podcast, but you can still listen to this show on YouTube by searching for “Ray Kondler.” While this show ran twelve years before the BBB tax bill, when I listened to it recently, Kondler impressed me and I came to the conclusion that I would like his firm to represent me.
Also on YouTube, when I searched for “Gary Kondler,” I found that he has appeared on several gambling related podcasts since the BBB came out, and I’m still convinced I want these guys representing me. You can listen to these podcasts as well if you like. My financial advisor has contacts with the Nevada Board of Accountancy and found out that the Kondler and Associates firm has a solid reputation. Richard Munchkin and I are interviewing him on GWAE the day this article is posted, and the podcast will probably be posted Wednesday December 24.
I’m convinced enough that I plan to hire the firm and continue my gambling career. I am not an expert in this field, and everybody’s tax situation is different. Keep in mind that I am making no recommendation for you or anybody else.
If I’m wrong on trusting Kondler’s methodology, continuing gambling could be a very expensive decision for me. It will be a few years before anybody knows for sure, because we’re taking about the 2026-and-beyond tax years and it takes a while after returns are filed to go through the system. And while the BBB is still the law today, who knows if it will be changed along the way?
I am willing to take that risk — for myself. Whether it’s correct for you to do similarly is something you’ll have to decide for yourself.
If you write emails to me, or post responses to this column, or ask me tax questions, my response will always be “I’m not a tax expert and I’m not qualified to answer your questions.”
