The interpretation timeline
Judges 9:9 Douay-Rheims

And it answered: Can I leave my fatness, which both gods and men make use of, to come to be promoted among the trees?

A.D. 311 – 1849 5 witnesses

Patristic

before A.D. 750
311
A.D.
c. A.D. 260–311
“But lest I should appear to some to be sophistical, and to conjecture these things from mere probabilities, and to babble, I will bring forward to you, O virgins, from the Old Testament, written prophecy from the book of Judges, to show that I speak the truth, where the future reign of chastity was already clearly foretold.…Now it is clear that these things are not said of trees growing out of the earth. Inanimate trees cannot be assembled in council to choose a king since they are firmly fixed to the earth by deep roots. But on the whole these things are narrated concerning souls that—before the incarnation of Christ—luxuriated too deeply in transgressions, who approach God as beggars asking for mercy so that they may be governed by his pity and compassion. This mercy is what Scripture expresses by the figure of the olive, because oil is of great advantage to our bodies: it takes away our fatigue and ailments and offers light. For all lamplight increases when nourished by oil. So also God's mercies entirely dispel death, assist the human race and nourish the light of the heart. Consider the laws [which were in effect] from the first created man successively on to Christ. Weren't they imaginatively set forth in these words by the Scripture, in opposition to which the devil has deceived humanity? In it the fig tree has been associated with the command given to the man in paradise, because, when he was deceived, he covered his nakedness with the leaves of a fig tree; and the vine [has been related] to the instruction given to Noah at the time of the deluge, because he was mocked when overpowered by wine. The olive signifies the law given to Moses in the desert, because the prophetic grace, the holy oil, had failed from their inheritance when they broke the law. Lastly, the bramble aptly refers to the law that was given to the apostles for the salvation of the world: by their instruction we have been taught virginity, which is the only figure that the devil has not been able to make into a deceptive image. For this reason, also, the four Gospels have been given, because God has four times given the gospel to the human race and has instructed them by four laws, the times of which are clearly known by the diversity of the fruits. For the fig tree, on account of its sweetness and richness, represents the delights of man, which he had in paradise before the fall. Indeed, as we shall afterwards show, the Holy Spirit frequently takes the fruit of the fig tree as an emblem of goodness. But the vine, on account of the gladness produced by wine and the joy of those who were saved from wrath and from the deluge, signifies the change produced from fear and anxiety into joy. Moreover, the olive, on account of the oil that it produces, indicates the compassion of God, who again, after the deluge, bore patiently when people turned aside to ungodliness, so that he gave them the law and manifested himself to some, and nourished by oil the light of virtue, which is now almost extinguished.”
Source
430
A.D.
Augustine of Hippo Patristic
A.D. 354–430
“And no one has been so illiterate as to think that similar fables of Aesop, related for the same purpose, ought to be called lies. But also in the sacred writings such passages are found, as in the book of Judges the trees look for a king to rule over them and speak to the olive and the fig and the vine and the bramble. Surely, all this is invented in order that we may reach the matter intended by means of a narrative [that is] fictitious, to be sure, but bearing a true and not a false signification.”
Source

Scholastic

c. 1100 – 1500
1105
A.D.
Rashi Jewish
1040–1105
“The richness of my oil. The connotation here is fattiness.”

Post-Reformation

c. 1650 – 1900
1771
A.D.
John Gill Reformed
1697–1771
“But the olive tree said unto them,.... In reply to the request of the trees: should I leave my fatness, wherewith by me they honour God and man; by "fatness" oil is meant, pressed out of the fruit of the olive tree, and which was much made use of both in the burning of the lamps in the tabernacle, and in many sacrifices, as the meat offerings and others, whereby God was honoured; and it was also made use of in the investiture of the greatest personages with the highest offices among men, as kings, priests, and prophets, as well as eaten with pleasure and delight by all sorts of men, and even by the greatest, and so men are honoured by it: and go to be promoted over the trees; desert so useful a station, in which it was planted and fixed, to move to and fro, as the word signifies, and reign over trees; suggesting that it was unreasonable, at least not eligible to a good man to desert a private station in life, to which he was called of God, and in which he acted with honour and usefulness to others, and take upon him a public office, attended with much care and trouble, and with neglect of private affairs, and with the loss of much personal peace and comfort.”
Source
1849
A.D.
1774–1849
“Leave. But, would this advancement prove any disadvantage? The king is bound to give himself up wholly for the good of the public, so that he must frequently be full of anxiety and care. (Calmet) — Use of. The olive-tree is introduced, speaking in this manner, because oil was used, both in the worship of the true God, and in that of the false gods, whom the Sichemites served. (Challoner) — The pagans burnt lamps in honour of their idols, and anointed their statues: unguentoque lares humescere nigro. (Prud., contra Sym. 1.) — They also anointed their military standards at Rome. (Pliny, [Natural History?] xiii. 3.) — The same author observes, that “two sorts of liquor are very delightful to the bodies of men: wine to drink, and oil for the outside: intus vini, foris olei. (B. xiv. 22.) — Men use oil to strengthen and foment their bodies, as well as to give them light. (Calmet) — It spiritually denotes the grace of God, which establishes the peace of the soul, as the fig-tree signifies the sweetness of God’s law, producing good works, and the vine shews forth those noble actions, which are performed without the affection of outward show; and which are therefore, most agreeable both to God and to men. (Worthington) — Promoted. Some translate the Hebrew, “to put myself in motion for,” Syriac, &c. We might also render, “which honoureth the gods, (or the judges) and men to come to be promoted among (or disquieted on account of) the trees.””
Source
Modern · 1953 →

The in-app commentary runs from the Fathers to the early-modern record, then stops — that's where the public-domain sources end, not where the reading does. For the modern reading, follow the sources directly.