I am teaching a writing-intensive course this semester, and one challenge is how to deal with students who “aren’t good at grammar.” On the one hand, one does want to help them write in the way generally recognized as “proper.” On the other hand, there is a level at which one must admit that there is something unjust about the way arbitrary conventions are used to judge intelligence — someone who writes in a non-standard way is not regarded simply as non-conformist, but is often judged as being somehow dumb.
In reality, however, it seems that many of our conventions are not only dumb in themselves, but superfluous. For instance, take the use of the apostrophe to designate either possessives or contractions. It seems to me that these apostrophes do not actually add any information that is not already supplied naturally by the context — if you left out all apostrophes, you could still tell which words were contractions (as opposed to homographs like “wont” and “cant,” which are rare to begin with) and, even more radically, I contend that you could tell whether it was a plural, a possessive, or a plural possessive.
To demonstrate this bold claim, I challenge our readers to come up with a sentence that is (a) somewhat plausible and (b) could be genuinely ambiguous if plurals/possessives were not distinguished using apostrophes.