The UPS case is the last big captive case. However, there is a bit of history between UPS and Harper that we need to explain before moving forward.
In the 1990s, the IRS expanded the scope of their captive litigation, targeting bigger companies. Humana was one of the first truly large, fortune 500 style companies subject to captive litigation. It was not the last. Harper (which I discussed last week) was a large, international company. The service went so far as to argue Allstate — then a subsidiary of Sears — was a captive, even though Allstate wrote a a very small part of their business with Sears. UPS fits with this general case theory of the service generally targeting larger companies after establishing a legal foundation with smaller companies. However, this tactic did not work. The dam started to burst with the Humana (see here, here and here). Read More
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