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ABISHAI (a-bĭsh'ā-ī, Heb. ’ăvîshay, meaning is doubtful). Son of David’s sister Zeruiah, and brother of Joab and Asahel. He was impetuous and courageous, cruel and hard to his foes, but always intensely loyal to David. He counseled David to kill the sleeping Saul (1Sam.26.6-1Sam.26.9). He aided Joab in the murder of Abner, an act of revenge for the slaying of their brother Asahel (2Sam.3.30). He was loyal to David when Absalom and Sheba revolted, and he wanted to kill Shimei for cursing David (2Sam.16.5-2Sam.16.14). He defeated a large army of Edomites (1Chr.18.12-1Chr.18.13). Late in David’s life he rescued the king in the fight with Ishbi-Benob, the Philistine giant (2Sam.21.17).

ABISHAI ə bī’ shī (אֲבִישַׁ֔י, in 1 Chronicles אַבְשַׁ֛י. Meaning uncertain. The suggestions my father is Jesse, he is my father, or my father exists are all unlikely). The oldest son of Zeruiah, a sister of David, and the brother of Joab and Asahel (1 Chron 2:16).

Abishai first appeared with David in the wilderness of Ziph when pursued by Saul. Abishai volunteered to go with David into the center of Saul’s sleeping army. Standing by the somnolent Saul, he offered to kill him with one thrust of his sword, but David restrained him (1 Sam 26:6-9).

In the warfare between Judah and Israel after the death of Saul, Abner killed Asahel. Sometime later Abner decided to assist David in acquiring the throne over Israel. Nevertheless, Abishai assisted Joab in murdering Abner in revenge for the killing of Asahel. David declared himself and his kingdom guiltless of the murderous act of Joab and Abishai (2 Sam 2:18, 24; 3:30).

During Absalom’s rebellion, Abishai remained loyal to David. When David left Jerusalem surrounded by his mighty men, Shimei of the family of Saul cursed David and threw stones at him from a nearby hillside. Aroused to anger, Abishai said: “Why should this dead dog curse my lord the king? Let me go over and take off his head” (2 Sam 16:9). Here, again, David restrained Abishai’s impetuous, bloodthirsty spirit (v. 11). Abishai was set over one-third of David’s army to resist the attack of the Israelite army of Absalom under Amasa at Gilead (2 Sam 18:2). With Joab and Ittai, Abishai was ordered by David to “Deal gently for my sake with the young man Absalom” (2 Sam 18:5). In battle with the Ammonites assisted by the Syrians, Abishai attacked the Ammonite sector while Joab attacked the Syrians. Joab and Abishai were successful in their respective battles (2 Sam 10:10, 14). Abishai commanded an army which conquered the Edomites, killing 18,000 Edomites and placing garrisons in Edom (1 Chron 18:12, 13).

In David’s old age Abishai rescued him from death when he was pressed by a Philistine giant in a battle with the Philistines. The giant Ishbibenob was slain by Abishai. As David returned to Jerusalem after the death of Absalom, though Shimei welcomed David and confessed his sin, Abihsai said: “Shall not Shimei be put to death for this, because he cursed the Lord’s anointed?” (2 Sam 19:21). Once more David rebuked and restrained Abishai. In the struggle to regain control of the nation after Absalom’s rebellion, Joab killed Amasa, and Joab and Abishai pursued Sheba the son of Bichri, a Benjamite, who instigated rebellion against David. The pursuit ended in the dispersal of Sheba’s army and his death.

Abishai prob. died before the struggle between Adonijah and Solomon because he is not mentioned on either side of that conflict.

International Standard Bible Encyclopedia (1915)

ab’-i-shi, a-bi’-shi (’abhishai, in Ch ’abhshai; meaning is doubtful, probably "my father is Jesse," BDB): Son of Zeruiah, David’s sister, and one of the three famous brothers, of whom Joab and Asahel were the other two (2Sa 2:18). He was chief of the second group of three among David’s "mighty men" (2Sa 23:18).

He first appears with David, who was in the Wilderness of Ziph, to escape Saul. When David called for a volunteer to go down into Saul’s camp by night, Abishai responded, and counseled the killing of Saul when they came upon the sleeping king (1Sa 26:6-9). In the skirmish between the men of Ishbosheth and the men of David at Gibeon, in which Asahel was killed by Abner, Abishai was present (2Sa 2:18,24). He was with and aided Joab in the cruel and indefensible murder of Abner, in revenge for their brother Asahel (2Sa 3:30).

In David’s campaign against the allied Ammonites and Syrians, Abishai led the attack upon the Ammonites, while Joab met the Syrians; the battle was a great victory for Israel (2Sa 10:10-14). He was always faithful to David, and remained with him, as he fled from Absalom. When Shimei, of the house of Saul, cursed the fleeing king, Abishai characteristically wished to kill him at once (2Sa 16:8,9); and when the king returned victorious Abishai advised the rejection of Shimei’s penitence, and his immediate execution (2Sa 19:21).

In the battle with Absalom’s army at Mahanaim Abishai led one division of David’s army, Joab and Ittai commanding the other two (2Sa 18:2). With Joab he put down the revolt against David of Sheba, a man of Benjamin (2Sa 20:6,10), at which Joab treacherously slew Amasa his cousin and rival, as he had likewise murdered Abner, Abishai no doubt being party to the crime. In a battle with the Philistines late in his life, David was faint, being now an old man, and was in danger of death at the hands of the Philistine giant Ishbihenob when Abishai came to his rescue and killed the giant (2Sa 21:17). In the list of David’s heroes (2Sa 23) Abishai’s right to leadership of the "second three" is based upon his overthrowing three hundred men with his spear (2Sa 23:18). He does not appear in the struggle of Adonijah against Solomon, in which Joab was the leader, and therefore is supposed to have died before that time.

He was an impetuous, courageous man, but less cunning than his more famous brother Joab, although just as cruel and relentless toward rival or foe. David understood and feared their hardness and cruelty. Abishai’s best trait was his unswerving loyalty to his kinsman, David.