What does Obadiah 1:16 mean?

In the Bible, judgment is often symbolized by drinking from a cup. It's possible that part of the "gloating" Edom did when Jerusalem was sacked included drinking and celebration (Obadiah 1:13). In this case, the imagery seems to be that of a people who are so unaware, and so drunk, that they drink themselves to death.

Old Testament prophecy sometimes refers to "the day of the Lord," which can mean several things. In some cases, it means some immediate, upcoming day of reckoning. In others, it's a reference to the return of Christ and the beginning of the millennial kingdom. In verse 16, the end-times destruction of these nations is predicted to be absolute. Not long after this prophecy, Edom was driven from their land. Centuries later, they were all but erased by Rome. Someday, all of the nations who reject God will be destroyed so completely, it will be as if they never existed at all (Revelation 19:15).