Why does the Zechariah verse say the King Messiah is riding a donkey AND a foal, the offspring of the donkey? Is this a translation issue?
Source: Judaica Press (Chabad.org)
The literal translation would seem to be as you suggest. Here it is in the original Hebrew, with my translation:
גִּילִ֨י מְאֹ֜ד בַּת־צִיּ֗וֹן הָרִ֙יעִי֙ בַּ֣ת יְרוּשָׁלִַ֔ם הִנֵּ֤ה מַלְכֵּךְ֙ יָ֣בוֹא לָ֔ךְ צַדִּ֥יק וְנוֹשָׁ֖ע ה֑וּא עָנִי֙ וְרֹכֵ֣ב עַל־חֲמ֔וֹר וְעַל־עַ֖יִר בֶּן־אֲתֹנֽוֹת׃
Rejoice greatly, daughter of Zion; shout, daughter of Jerusalem. Behold, your king will come to you, a righteous man and a savior. A poor man, and one who rides on a donkey, and on a foal, son of she-donkeys.
While the Malbim doesn’t ask your question, his explanation of the passuk indirectly addresses it. He interprets various attributes in the verse as indicating that Mashiach will be “reversing” their usage; for instance, a savior appointed by the king is usually bedecked in the finest outfit, yet Ben David is described as a “poor man.” Regarding the final stitch of the verse he writes:
ורוכב על חמור הפך רוכב על סוס מוכן ליום מלחמה, וגם אם ירכב על עיר שהוא צעיר לימים שזה כבוד יותר, (כמ"ש רוכבים על שלשים עירים שופטים י' ד'), לא יהיה עיר בן סוס רק עיר בן אתונות:
“And riding on a donkey” - he reverses riding on a horse, which is designated for the day of war; and also, if he is “riding on a foal” which is young in days, which is a greater honor (as we see in Judges 10:4), it will not be the foal of a horse, but rather the foal of she-donkeys.
By explaining the passuk in this manner, he necessarily translates the ו in ועיר not as “and” but as “or”:
A poor man, and one who rides on a donkey, or a foal, son of she-donkeys.
Radak explains much less Midrashically that the passuk is just stylistically repeating itself:
ועל עיר בן אתונות. כפל הענין במילות שונות ועוד זכר עיר שהוא קטן בשנים כי הוא הנבחר לרכוב וכן אמר על בני אבצן רוכבים על שלשים עירים:
“And on a foal, son of she-donkeys.” The idea is duplicated in different words; and further, [it uses] a male foal, which is small in years, for it is the most treasured on which to ride. And so does it say regarding the children of Ivzan [also in the book of Judges], “riding on thirty foals.”
He therefore would translate the verse as:
A poor man, and one who rides a donkey which is a foal, son of she-donkeys.
I am unaware of another usage of a conjunctive ו being used in this manner; if someone knows of one, please ping me.
While your translation seems to be the common one (I see that, for instance, JTS, quotes by Sefaria, uses the conjunction “and” as well), I do not see any commentators that defend this translation. Once again, if anyone finds one, please ping me.