Vine's Expository Dictionary of OT Words
'Esher (אֶשֶׁר, Strong's #835), “blessed; happy.” All but 4 of the 44 biblical occurrences of this noun are in poetical passages, with 26 occurrences in the Psalms and 8 in Proverbs.Basically, this word connotes the state of “prosperity” or “happiness” that comes when a superior bestows his favor (blessing) on one. In most passages, the one bestowing favor is God Himself: “Happy art thou, O Israel: who is like unto thee, O people saved by the Lord” (Deut. 33:29). The state that the blessed one enjoys does not always appear to be “happy”: “Behold, blessed [KJV, “happy”] is the man whom God correcteth: therefore despise not thou the chastening of the Almighty: for he maketh sore, and bindeth up …” (Job 5:17-18). Eliphaz was not describing Job’s condition as a happy one; it was “blessed,” however, inasmuch as God was concerned about him. Because it was a blessed state and the outcome would be good, Job was expected to laugh at his adversity (Job 5:22).
God is not always the one who makes one “blessed.” At least, the Queen of Sheba flatteringly told Solomon that this was the case (1 Kings 10:8).
One’s status before God (being “blessed”) is not always expressed in terms of the individual or social conditions that bring what moderns normally consider to be “happiness.” So although it is appropriate to render 'esher as “blessed,” the rendering of “happiness” does not always convey its emphasis to modern readers.
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Vines, W. E., M. A. Entry for 'Blessed'. Vine's Expository Dictionary of OT Words. https://www.studylight.org/dictionaries/eng/vot/b/blessed.html. 1940.