This verse may be the epitome of Jesus's mastery of wordplay, not just in the choice of words, which could be captured in translation but isn't, but also in the word order creates suspense and surprise that is way lost in any translation. He does this by putting the verbs first, following later, after misleading words, with the subject. For the listener, his words offer a series of surprises, a roller coaster of shifting meanings.

For example, the second clause beginning six words in Greek. It seems to start, "When it becomes," but the "becomes" is followed by an indirect object "to some man." This changes the meaning of "becomes" to "produced or belongs." Still no subject. Then comes the "hundred," which doesn't seem to indicate a subject either because the subject is singular and a hundred is plural.  Then, finally, the subject noun appears, "sheep," which, though plural matches the singular verb because plural neuter nouns like "sheep" are usually treated as a single conglomeration. Everything works out as perfectly grammatical Greek, but what a wild ride for the listener.

The word translated as "gone astray/wonders" also begins its clause, and its meaning also changes as the rest of the cause is revealed. First, its verbal form makes it part of the "when" clause, something that might happen along with a man owning a hundred sheep. The verb could mean "wanders" or "be misled." The subject, "one" doesn't clarify what is happening since it could refer either to one sheep or the flock. The meaning doesn't become clear until the phrase "away from them."

The ending of this verse plays a similar trick on the listener, one that can be understood only by tone of voice. The initial words say the exact opposite of Jesus's meaning until we realized that it is a question. It literally says "Certainly he won't leave the ninety-nine sheep on a mountain...." This makes perfect sense, but what happens to the meaning if inflection changes this phrase into question? It then becomes, "Certainly, won't he leave the ninety-nine on a mountain?" Same exact words. Opposite meaning. It is like a magic trick.

And yet look at the below analysis to see how this verse cramped into a simple, "no fun" meaning.