...Here, the government stretched the obstruction law to reach any act “that has the natural tendency to obstruct or impede the IRS in an unlawful manner to obtain an unlawful benefit.”
For example, the government argued that if you pay someone $100 in cash for a service—say, to clean the gutters—and “that is then not reported to the IRS or is falsely reported to the IRS,” that could be obstruction.
Breyer aptly noted that such a dragnet carries a “lack of fair warning and related kinds of unfairness” that have led the court in prior cases to “‘exercise’ interpretive ‘restraint.’” That line of cases is long indeed (including Aguilar, Arthur Andersen, Bond, McDonnell, McNally, McCormick, Sun-Diamond Growers, Skilling, and Yates).
According to the National Federation of Independent Business, if the court had bucked that trend and upheld the government’s position in Marinello, “that would have greatly complicated tax compliance for small businesses, who already spend inordinate time, energy, and money on tax issues,” the federation argued. “And worse, it would have opened the doors for prosecutions against businesses for engaging in completely legitimate practices simply because the government alleges that business might have had some improper motive”—namely, cheating the tax man....