Baldness: The reference is to shaving of the head, which was a sign of “Great sorrow” (Good News Translation). The same thing is true of self-inflicted gashes (how long will you gash yourselves?), which follows three lines below. See 16.6. Good News Translation has dropped the symbolic acts themselves to express only the meaning, “Great sorrow” and “mourn.” Some translators retain both the image and the basis of the comparison: “The people of Gaza have shaved their heads to show their sorrow,” and “gash [or, cut] yourselves in mourning.” Of course, the meaning of the symbolic acts can also be put in a footnote.
Ashkelon: See 25.19-26.
Has perished: Some scholars interpret the word as “are silenced” or “are silent.” The meaning is similar, since if the city were dead, it would be silent. Thus translators can render “have perished,” “are silent,” or “have been silenced.” Of course, the translation can be either that the city Ashkelon has perished or that the people there have, depending on the language.
O remnant of the Anakim: As the Revised Standard Version note indicates, the rendering Anakim follows the Septuagint; the standard Hebrew text has “their valley,” hence translations, such as New Jerusalem Bible, have “You who remain in the valley.” But others, for example New International Version, have “remnant on the plain.” The difference in Hebrew is merely one consonant, which could easily have been changed in copying the ancient Hebrew script. If Anakim was the original text, then the reference is to the old race of giants (see Num 13.33; Deut 9.2). Bible en français courant follows this with “You, the survivors of the giants.” It is possible that the Hebrew word rendered “valley,” may also have a meaning that is the equivalent of “strength.” If this is the case, then we may render “the remnant of their strength,” meaning “those who are left alive.” Revised English Bible, for example, has “the remnant of the Philistine power.” This is also the basis for Good News Translation “How long will the rest of Philistia mourn?”
Quoted with permission from Newman, Barclay M. and Stine, Philip C. A Handbook on Jeremiah. (UBS Helps for Translators). New York: UBS, 2003. For this and other handbooks for translators see here .