Something up with which I will not put

If you're a Winston Churchill fan, you no doubt recognize my post title. Although it may well be apocrypal, many grammarians (or perhaps I should say "grammar rebels") tell of the day Churchill received a manuscript back from his publishing company, only to discover that some editor had turned one of his more elegant sentences into a garbled mess in order to avoid leaving a preposition at the end. The affronted Churchill returned the manuscript after writing a pungent message: "This is something up with which I will not put." (You may also have heard a more vulgar joke on the same topic about the Harvard and/or Yale man, but I'll just link you to that one, rather than reproducing it here.)

Both these stories make a good point: you can easily destroy a good sentence by engaging in all sorts of convoluted stylings aimed at keeping that preposition away from the end of your sentence. Bryan Garner, whose approach to style I so much admire, is adamant that "no prepoposition at the end of a sentence" rule is a pointless relic. I, however, would not be quite so quick to abandon this rule.

One of the things I've discovered in my many years as a legal writer is that, in the first draft at least, it's very useful to make an effort to abide by hoary old grammar rules. Why? Because they force you to consider very carefully the word order in your sentence.

As my children discovered recently when watching Mary Poppins, word order matters. Or have you forgotten the pivotal joke in that movie, a joke that brought down Mr. Banks' career (only to raise it up again at the end):

Bert: Speaking of names, I know a man with a wooden leg named
Smith.
Uncle Albert: What's the name of his other leg?

Although that joke revolves around a misplaced modifier (which is always one of my favorite grammatical errors because of the humor it usually provides), the principle is the same: put the words in the wrong place in your sentence, and you change your meaning. One of the ways to make quite sure you've got words in their proper order is to follow boring old rules of grammar: don't split your infinitives, don't use passive voice, and don't end the sentence with a preposition.

If you abide by these rules, your sentence may, in the first draft, sound a little awkward, indeed Victorian, but it will make perfect sense. Once you've taken care of the sense, instead of then hoping that the sounds will take care of themselves, you can have some fun massaging your sentence into something more user friendly -- a task that might require you to break some or all of the basic grammar rules. When you do so, however, it will be a conscious effort, and you're unlikely to end up with a garbled mess that defies any attempt to decipher it.

By the way, lest you think I'm advocating rewriting every single sentence in your brief, I'm not. Most sentences write themselves, especially when you're not trying to finesse your way around something troublesome. You need to start paying attention, though, either when you're dealing with very complex concepts or when you (on behalf of your client, of course) are trying to avoid taking responsibility for something unpleasant. Under those circumstances, it's quite common for lawyers to start writing squiggly sentences that have ideas leaking in different directions and no one taking responsibility for anything at all.

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