Owner: Jerry Reinsdorf

Wealth: Real estate tax loophole

Reinsdorf is one of the most well-known owners in the NBA, mostly owing to him breaking up the MJ-led Bulls. He also owns the Chicago White Sox. He made his money by taking advantage of a loophole in the IRS tax code for real estate in 1978 (which was amended in 1986). For those tax attorneys out there, Reinsdorf was allowed to sell his real estate holdings to a holding company, lease it from this fake company, but take the tax deductions for depreciation for himself. In essence, he made money and never had to pay taxes on it.

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