Loopholes Archives - Page 5 of 19 - Think Outside the Tax Box
By Peter J Reilly CPA

Rolexes From Casino Points Instead Of Paying Taxes

The Jeffrey Winick tax story is about one of the simplest methods of not paying taxes. That simple method of not paying is simply not paying. Winick is a very successful real estate broker specializing in retail leases. The company he founded, Winick Realty (now rebranded RTL), has in the past been listed as one the top five of retail brokers in New York City. As far as my friend Grok can discern, Winick managed all this with no formal education beyond high school. That makes it extra impressive. I identify with him just a bit. He grew up in Kew Gardens Hill, Queens, New York, and is 75 years old. I also grew up not far from Manhattan and am 74. I sometimes fantasize about living in Manhattan. He's living there, and apparently he was really living. His lifestyle was a major topic in the litigation.

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TAX COURT ROUNDUP – May 2025

Once again, Tax Court provides slices of life as well as hyper-technical drilldowns into convoluted legal conundrums. To any who say that tax law is dull, I refer them to the annals of 400 Second Street, NW, where anything goes.

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2025 Summer Education Series Event Calendar

We are thrilled to bring you the 2025 Summer Education Series, sponsored by Vistia! All summer long we will be bringing our loyal subscribers monthly webinars featuring some of the brightest minds in tax. Each webinar will feature our usual blend of high-quality education and entertainment and include continuing education credits for those who qualify. All of this is included in your regular subscription! Continue reading to see what we have in store...

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2025 Spring Fling Webinar Event

As we prepared our 4th Annual Summer Education Series, our friends at Sandy Bay challenged us to go bigger and do even more live events than we originally planned. So, we did! We are proud to present Think Outside the Tax Box's first ever “Spring Fling” live webinar event. As a monthly or annual subscriber, this webinar is 100% exclusive, and free to you! Every webinar comes with free continuing education credits for those who qualify! Keep reading for more details...

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TAX COURT ROUNDUP – April 2025

Some new developments arose in March and some new gimmicks. The current hot topics, microcaptive insurers and syndicated conservation easements, remain on the front burner.

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TAX COURT ROUNDUP – March 2025

February brings us Groundhog Day, but there are always new developments in Tax Court, as well as refreshers to keep practitioners current.

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Pig Butchering Can Slaughter Your Clients’ Finances

People use the online space to look for love, make business and financial decisions. And all of these decisions can have serious tax implications. That is why as trusted financial and tax advisors, it is important for us to be aware so we can help protect our clients. In 2024, the Federal Trade Commission released a report showing consumers reported losing $4.6 billion in investment scams. That's only the amount reported, so our clients are at risk if they are online making financial decisions. Today, let's look at a newer player in the online investment scam arena: pig butchering. If you're like me, you're probably thinking “what in the world does this have to do with taxes?” Unfortunately, everything. It leads to taxpayers receiving tax bills for money they withdrew but lost as victims of theft.

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TAX COURT ROUNDUP – February 2025

When we enter upon a new Administration, we wonder at the shape of things to come. But surely since 1916, we have never had an incoming Administration promise us a repeal of the income tax and the reestablishment of the import tariff as the principal source of Federal funding. I would not, however, immediately cease to follow the proceedings of the US Tax Court.

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Is Student Loan Forgiveness Taxable? It Depends…

Is student loan forgiveness taxable? Yes. No. Maybe. Sometimes. It primarily depends on the student loan forgiveness program. But like everything else with student loans, there are a number of other factors at play. Why make it easy when you can thoroughly confuse taxpayers, federal student loan servicers and financial planners for years to come? Keep reading to learn when student loan forgiveness might be tax-free and how to prepare your clients for taxable loan forgiveness.

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