“not…will ever.” This phrase is constructed in the Greek by ou me, an intensified form of “no.” Literally, it is composed of two words for no, “no not.”
“smallest letter.” Matthew 5:18 is an interesting study in translation. The ESV says, “For truly, I say to you, until heaven and earth pass away, not an iota, not a dot, will pass from the Law until all is accomplished. But what are an “iota” and a “dot.” An “iota,” is the smallest letter in the Greek alphabet, and the “dot” is from the Greek keraia, which means “little horn.” Of course, Jesus was speaking Hebrew or Aramaic to his audience, and the King James Version picked up on that and brought the Greek into Hebrew, using “jot,” which is more properly “yod,” the tenth and smallest letter in the Hebrew alphabet, and tittle, which are the little horns or ornaments on nicely drawn letters in the Hebrew text. Most modern translators do not want to force their readers to know details of Greek or Hebrew, and so translate the phrase something such as, “not the smallest letter, not the least stroke of a pen,” as the NIV does. The point of what Jesus was saying was that nothing would pass from the Law until all was fulfilled.