The statute sounds simple. A criminal defendant faces enhanced penalties if he has previously been convicted of three felonies committed on "occasions different from one another." But the defendant in Wooden v. United States, decided by the U.S. Supreme Court this week, was convicted of ten burglaries on the same night, in the same place. Were those ten different "occasions"?

The government urged the Court to answer by adopting a time-based categorical rule: Unless the crimes were simultaneous, they occurred on different occasions. So when Wooden burgled ten storage units, one after another, the government saw each crime as a different occasion.

The Supreme Court disagreed. Applying the ordinary meaning of the word "occasion" and analogizing to occasions as disparate as a wedding and a barroom brawl, the Court explained that deciding whether crimes occurred on more than one occasion required a "multi-factored" inquiry. Time, location, and the connection between the crimes all may matter, depending on the circumstances. Wooden's burglaries, which happened on one night, in one place, as part of one scheme, counted as one occasion.

The categorical rule proposed by the government would have been easier. Categorical rules create bright lines, so those who must follow them enjoy more certainty. In Wooden, however, the Supreme Court relied on the statute's ordinary meaning to adopt a far dimmer line.

I see two lessons here for anyone facing a difficult question of statutory interpretation.

First, as much as appellate courts prefer to announce easy-to-apply, bright-line rules, sometimes messy, ordinary meaning matters more. Matching the facts of your case to the words in a statute or rule can win the day, even if it can't answer every oral argument hypothetical. The Supreme Court's decision in Wooden says that sometimes those knotty hypotheticals will just have to wait for their own day in court.

Second, the Court in Wooden grounded its decision in the Justices' intuition about what the word "occasion" meant. Dictionaries from the time of the statute's enactment were referenced, but the Court relied more on analogies than formal definitions. The Court asked "how an ordinary person (a reporter; a police officer; yes, even a lawyer)" would use the word, and it stuck with that answer.

For an appellate lawyer, an intuition like that is a vital, hard-won skill, built on a devotion to reading and language. A difficult interpretive question can usually be approached from many different directions. It helps to have a good sense of where to start.