2. The Extra Day Swindle
In February 1997, John Melo was convicted of home invasion and sentenced to ten years and one day in prison. Seven years later, he filed a motion complaining that the Department of Correction had miscalculated the length of his sentence. Why? Because it had failed to credit him for the additional days he had to serve on account of the February 29's during leap years.
Melo's motion was allowed, but he didn't win the case. In 2006 the Superior Court ruled (Commonwealth vs. John Melo) that not only did his case have no merit, but it had been a mistake to ever allow it to proceed in the first place, noting that he had clearly been sentenced to a term of years, no matter how long each year may be.