Rolexes From Casino Points Instead Of Paying Taxes - 06-15-26 episode artwork

EPISODE · Jun 15, 2026 · 18 MIN

Rolexes From Casino Points Instead Of Paying Taxes - 06-15-26

from Think Outside the Tax Box · host TOTTB-Pod

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. According to the RTL site:"Jeff has personally overseen millions of square feet of leasing transactions, working on behalf of clients such as AT&T, Duane Reade and Chase Bank, as well as prominent property owners and developers like SL Green, Brookfield, The Moinian Group, Chetrit Group, Related Companies, Lalazarian Developers, TF Cornerstone, Vornado and the Stahl Organization, among many others. Jeff has successfully negotiated retail leases for new locations for such renowned retailers as Paris Baguette, Burlington, Five Below, Home Goods, Those House of Cannabis; THCNYC, The NBA Store, Nordstrom Men’s Store, Nordstrom Rack, TJ Maxx, REI, Whole Foods and countless others."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.This podcast is meant for entertainment purposes only. For the more thorough, complete, and accurately written version of this article which includes citations, visit us at http://www.tottb.tax

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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. According to the RTL site: "Jeff has personally overseen millions of square feet of leasing transactions, working on behalf of clients s...

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Rolexes From Casino Points Instead Of Paying Taxes - 06-15-26

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