punctuation - Rules about prepositions and duplicating 'to'
On occasion, I end up writing sentences that contain a duplicate word, often what is probably a preposition (or better yet, an adposition). The specific example that I just ran into involves a duplicate 'to' in this sentence:
I think we really ought to leave that up to the people we're assigning the label to to judge.
Is this proper grammar? If it is so technically, is it proper style to leave it like that, or should it be rephrased, so one doesn't stumble over it when reading?
Should there be a comma between the two?
Answer
While your sentence
I think we really ought to leave that up to the people we're assigning the label to to judge.
is not grammatically incorrect, it would be considered inelegant by many writers, especially because it involves a duplicate preposition. (It is not uncommon to find "...had had..." in formal contexts and this is not usually frowned upon.) So, you are right your construction is not stylistically preferred. Also, there should not be a comma between the duplicates.
Here are possible revisions in increasing order of elegance:
I think we really ought to leave that up to the people to which we're assigning the label to judge.
I think we really ought to leave that judgment up to the people to which we're assigning the label.
I think we really ought to leave that judgment up to the people whom we're labeling.
I think we really ought to leave that up to the people we're labeling to judge.
I think we really ought to leave that judgment up to the people we're labeling.
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