Cullather v. Commissioner:
When tax laws get complicated...
The 2010 Affordable Care Act was a very long bill and had many smaller and more interesting provisions. (I think my favorite was the amusing "tanning bed tax") One of these provisions was a tax on "net investment income", which is exactly what it sounds like - an extra tax for high income earners on things like dividends, royalties, and stock sales. However, the new tax distinguished between investment income and income related to "a trade or business."
Cullather was a case about a local NYC founder and CEO who sold his company for a large sum; the issue in the case was whether the sale of the company was "investment income" subject to the tax, or rather, income related to his "trade or business" which was exempt from the tax. The distinction was not a trivial one - the total tax and penalty was around $500,000. At the time, it was the third largest dispute I'd handled as a tax attorney in terms of dollar value.
In tax disputes, the United States is represented by the Office of Chief Counsel of the Internal Revenue Service; they have multiple offices around the country, including two in downstate New York. Typically I will try to persuade the attorneys at Office of Chief Counsel to correct a tax bill before taking the dispute further; this is often successful since they are public servants just as judges are. The Cullather case was an example of this; I was successfully able to persuade IRS attorneys to cancel the $500,000 bill without needing to escalate the case further.
While TV and movies often glamorize trial victories and courtroom drama, in the real world, your goal as a tax attorney is to keep your clients out of court. Although I was happy to prepare witness testimony and present various evidence of my client's successful business venture (including articles in various publications), Cullather was a success because I was able to avoid this hassle.