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Notes -
There is no one second hypothetical here as there's no legal assumption that any of the events happened simultaneously — he dies, some time thereafter the insurance is paid out, and some time after that the company completes the redemption. In real life we're probably talking several months. At the time of Michael's death the company was worth 6.86 million, and it continued to be worth as much after his death.
And while the intent may have been clear, the means used had the effect of nearly doubling the company's value. It's easy to talk about intent, but eventually this devolves into "I intended to minimize my tax burden", and you end up having to give the benefit of the doubt to people who take actions wherein reducing the tax burden is clearly contrary to public policy. Practically any tax avoidance scheme, no matter how hard brained, becomes effective. The fact that convoluted schemes are often used is unfortunate, but it's the nature of the business.
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