Writers sometimes trip themselves up when they try to introduce a parenthetical element in a sentence without ensuring that the main clause of the sentence remains grammatically coherent. Here’s a troublesome example of this type of error, with a discussion of possible revisions.
In the sentence “Smith was one of, if not the first, female members of the organization,” the writer is attempting to communicate two related ideas too early in the syntactical structure: Smith was one of the first female members of the organization, and she may have been the first female member of the organization. The preceding sentence is a possible revision, but the two thoughts can be expressed more concisely.
To untangle the original sentence, revise it so that if the parenthetical element — what is positioned between the commas (or a pair of parentheses or dashes) — is deleted, what remains stands as a coherent sentence. The sentence without the parenthesis, “Smith was one of female members of the organization,” is not grammatically sound, because “the first” is expected to bear the responsibility of serving both points of the sentence. With the parenthesis, “female members” is expected to apply both to “one of” and “the first,” but the phrases are not parallel in structure.
How about aligning the two points by using “the first” in each phrase? “Smith was one of the first, if not the first, female members of the organization” is closer to correct, but the parenthetical phrase still doesn’t agree with “female members.” (I’ve also seen constructions like “Smith was one of the, if not the, first female members of the organization.” The sentence is valid if the parenthesis is deleted, but the full sentence, again, is not parallel in structure.)
Let’s try moving the phrase “female members” before the parenthesis: “Smith was one of the first female members, if not the first, of the organization.” That’s better, but it still reads awkwardly. How about moving “of the organization” before the parenthetical, too? (“Smith was one of the first female members of the organization, if not the first.”) The parenthetical is no longer a parenthetical — it’s just a truncated phrase tacked onto the end of the main clause that implies the wording “if not the first female member of the organization” — but the grammatical architecture is now sound.
Sometimes, as in this case, a sentence is flawed in form — it just won’t support a parenthetical element — and must be restructured. This post analyzes three similarly impaired sentences.