Reference: Abraham's Bosom
Easton
(Lu 16:22-23) refers to the custom of reclining on couches at table, which was prevalent among the Jews, an arrangement which brought the head of one person almost into the bosom of the one who sat or reclined above him. To "be in Abraham's bosom" thus meant to enjoy happiness and rest (Mt 8:11; Lu 16:23) at the banquet in Paradise. (See Banquet; Meals.)
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Fausets
In Roman times, their custom of reclining on Couches at meals prevailed among the Jews. Each leaned on his left arm, and so lay, as it were, in the bosom of the next below him. This position in the bosom of the master of the house was the place of honor (Joh 1:18; 13:23). To lie in Abraham's bosom was thus a phrase for blessed repose in closest nearness to the father of the faithful in the feast of paradise (Mt 8:11; Lu 16:23).
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Hastings
It was natural for the Jews to represent Abraham as welcoming his righteous descendants to the bliss of heaven. It was, also, not unusual for them to represent the state of the righteous as a feast. In the parable of Lu 16:19 ff. Jesus uses these figures to represent the blessedness of the dead Lazarus. He was reclining at the feast next to Abraham (cf. Mt 8:11). A Rabbi of the third century, Adda Bar Ahaba, uses precisely this expression as a synonym for entering Paradise. Other Jewish writings occasionally represent Abraham as in a way overseeing the entrance of souls into Paradise. 'Abraham's Bosom,' therefore, may very fairly be said to be a synonym for Paradise, where the righteous dead live in eternal bliss. There is no clear evidence that the Jews of Jesus' day believed in an intermediate state, and it is unsafe to see in the term any reference to such a belief.
Shailer Mathews.
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Morish
Abraham their forefather was believed by the Jews to be in the highest place of happiness, and their writings show that 'to be with Abraham' and to be in his bosom were terms they used to express the highest security and happiness. Our Lord therefore used an expression that was well understood by His hearers and needed no explanation. Lu 16:23. It stands in contrast to hell, or hades, and was therefore figurative of heaven.