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2 Samuel 18:5 (NIV)
The king commanded Joab, Abishai and Ittai, “Be gentle with the young man Absalom for my sake.” And all the troops heard the king giving orders concerning Absalom to each of the commanders.
2 Samuel 18:14 (NIV)
Joab said, "I'm not going to wait like this for you." So he took three javelins in his hand and plunged them into Absalom's heart while Absalom was still alive in the oak tree.
Why did Joab go ahead and kill Absalom?
Joab was the commander of David's armies. Before we can understand why he killed Absolom we need to understand what was going on within the royal household:
David’s firstborn son was Amnon (mother Ahinoam), who raped his half-sister Tamar (a daughter of David but by a different wife).
David's second son was Kileab (mother Abigail), but nothing else is recorded about him - perhaps he died.
Absolom was David’s third son (mother Maacah), and he was Tamar’s brother.
Absolom killed Amnon then tried to steal the throne from his father. Joab was commander of David’s armies and he killed Absolom, but against David’s wishes.
Adonijah was David’s fourth son (mother Haggith) and he also tried to steal the throne from his father David.
Joab (David’s nephew) then killed his cousin Amasa after David replaced Joab with Amasa as commander of his armies. Joab supported Adonijah’s bid for David’s throne.
Before David died, and after David had anointed his son Solomon as king, David got Solomon to promise he would have Joab killed. David had never forgiven Joab for killing Absolom (against his express instructions). Solomon entrusted Beniah, who was now commander of David's armies, and who had refused to support Adonijah's bid for the throne. Beniah was loyal to his father David.
Looks like Joab killed Absolom because he supported Adonijah as the next heir to David's throne. And Joab wasn't best pleased when he lost his position as one of David's mighty men. However, he didn't reckon with God's plans to put Solomon on the throne, and through him, would come the promised Messiah.
The words of Robert Burns spring to mind - something about the best-laid plans of mice and men going astray.
Research material into David’s wives and sons:
2 Samuel 2:2 – David’s wives: Ahinoam of Jezreel (Saul’s widow); Abigail (widow of Nabal of Carmel; 2 Samuel 3:2-5 – Maacah (daughter of Talmai, king of Geshur); Eglah. It is supposed that David also married Haggith and Abital.
2 Samuel 3:2-5 - Sons born to David in Hebron: Amnon the son of Ahinoam of Jezreel (David’s wife) Kileab the son of Abigail the widow of Nabal of Carmel (David’s wife) Absolom the son of Maacah daughter of Talmai king of Geshur (David’s wife) Adonijah the son of Haggith Sephatiah the son of Abital Ithream the son of David’s wife Eglah
1 Chronicles 3:1-4 repeat the six sons born to David in Hebron, where he reigned for seven years and six months. (Kileab is called Daniel) Then verses 5-9 list the sons born to David when he reigned in Jerusalem for 33 years (apart from his sons by his concubines):
Shammua, Shobab, Nathan and Solomon (mother Bathsheba) Ibhar, Elishua, Eliphelet, Nogah, Nepheg, Japhia, Elishama, Eliada, Eliphelet, and their sister Tamar.
More about Adonijah's unsuccessful bid for power in this article: https://www.gotquestions.org/Solomon-Adonijah-Abishag.html
Long before Absalom's rebellion, David made a special deal with Abner, commander of King Ish-bosheth's army in 2 Samuel 3:21
Then Abner said to David, “Let me go at once, and I will gather all Israel to my lord the king, that they may make a covenant with you, and that you may rule over all that your heart desires.”
So David dismissed Abner, and he went in peace.
Contrary to David's plan, Joab killed Asahel in cold-blooded murder in 2 Samuel 3:27
When Abner returned to Hebron, Joab pulled him aside into the gateway, as if to speak to him privately, and there Joab stabbed him in the stomach. So Abner died on account of the blood of Joab’s brother Asahel.
In this case, the Bible told us the reason: personal revenge. Asahel killed Joab's brother, so Joab killed him. There was a bonus in this killing, Joab eliminated a potential competitor. Like Joab, Asahel would have been a high ranking commanding officer working for David. So he had two personal reasons to disobey David.
Joab was instrumental in helping Absalom to regain the trust of his father king in 2 Samuel 14. Yet Joab and Absalom had a conflict at verse
29 Absalom sent for Joab in order to send him to the king, but Joab refused to come to him. So he sent a second time, but he refused to come. 30 Then he said to his servants, “Look, Joab’s field is next to mine, and he has barley there. Go and set it on fire.” So Absalom’s servants set the field on fire.
It is consistent with Joab's character that he bore a personal grudge against Absalom for damaging his property. Once again disobeying David, Joab killed Absalom in 2 Samuel 18:14. Then David demoted Joab a chapter later.
2 Samuel 19:13 And say to Amasa, ‘Are you not my own flesh and blood? May God deal with me, be it ever so severely, if you are not the commander of my army for life in place of Joab.’ ”
However, Amasa was a bit slow and not completely competent in this new post when David ordered him to pursue another rebel named Sheba son of Bikri in 2 Samuel 20. So David send out a second ordered to Abishai who outranked Joab at the time.
2 Samuel 20:6 David said to Abishai, “Now Sheba son of Bikri will do us more harm than Absalom did. Take your master’s men and pursue him, or he will find fortified cities and escape from us.” a 7So Joab’s men and the Kerethites and Pelethites and all the mighty warriors went out under the command of Abishai. They marched out from Jerusalem to pursue Sheba son of Bikri.
Joab's devious personality showed up for the 3rd time.
2 Samuel 14:8 While they were at the great rock in Gibeon, Amasa came to meet them. Joab was wearing his military tunic, and strapped over it at his waist was a belt with a dagger in its sheath. As he stepped forward, it dropped out of its sheath.
9Joab said to Amasa, “How are you, my brother?” Then Joab took Amasa by the beard with his right hand to kiss him. 10 Amasa was not on his guard against the dagger in Joab’s hand, and Joab plunged it into his belly, and his intestines spilled out on the ground. Without being stabbed again, Amasa died. Then Joab and his brother Abishai pursued Sheba son of Bikri.
Once again, Joab had eliminated a rival to his position, another relative of David besides Absalom.
How did David react this time?
He promoted him.
23 Joab was over Israel’s entire army; Benaiah son of Jehoiada was over the Kerethites and Pelethites;
There was a complex relationship between David and Joab. Joab got David's jobs done efficiently, including David's dirty jobs, like killing Absalom--satisfying for Joab and good for David's hold on the throne.
There is a great deal worth exploring, to me, in this saga but I've tried to stick to passages that have direct bearing on the question.
Technically, Joab was not the one who killed Absalom (tho he directed it). Not sure of importance of that tidbit.
2Sam. 18:14 (KJV) - Then said Joab, I may not tarry thus with thee. And he took three darts in his hand, and thrust them through the heart of Absalom, while he [was] yet alive in the midst of the oak.
ISA 2Sam. 18:14 - And~he-is-saying Joab not(-) so I-shall-wait to~faces-of~you and~he-is-taking three clubs in~palm-of~him and~he-is-pitching~them in~heart-of Absalom still~him living in~heart-of the~terebinth.
2Sam. 18:15 (KJV) - And ten young men that bare Joab's armour compassed about and smote Absalom, and slew him.
ISA 2Sam. 18:14 - And~they-are-surrounding ten lads ones-bearing-of gear-of Joab and~they-are-smiting Absalom and~they-are-(putting-to)-death~him.
Why did Joab orchestrate the killing of Absalom? Treason against King David (Absalom's father), and other wickedness.
2Sam. 16:22 - So they spread(5186) Absalom(53) a tent(168) upon(5921) the top(1406) of the house; and Absalom(53) went(935) in unto(413) his father's(1) concubines(6370) in the sight(5869) of all(3605) Israel.(3478)
King David so loved Absalom (unblemished and beautiful from to to head, with incredible hair) that his reason was impaired. Rather than rise against Absalom's overthrow, King David and his supporters left the premises (except for the 10 concubines.)
After the killing of Absalom, Joab had stern words for King David:
2Sam. 19:4 - But the king(4428) covered(3813) (853) his face,(6440) and the king(4428) cried(2199) with a loud(1419) voice,(6963) O my son(1121) Absalom,(53) O Absalom,(53) my son,(1121) my son!(1121)
2Sam. 19:5 - And Joab(3097) came(935) into the house(1004) to(413) the king,(4428) and said,(559) Thou hast shamed(3001) this day(3117) (853) the faces(6440) of all(3605) thy servants,(5650) which this day(3117) have saved(4422) (853) thy life,(5315) and the lives(5315) of thy sons(1121) and of thy daughters,(1323) and the lives(5315) of thy wives,(802) and the lives(5315) of thy concubines;(6370)
2Sam. 19:6 - In that thou lovest(157) (853) thine enemies,(8130) and hatest(8130) (853) thy friends.(157) For(3588) thou hast declared(5046) this day,(3117) that(3588) thou regardest neither(369) princes(8269) nor servants:(5650) for(3588) this day(3117) I perceive,(3045) that(3588) if(3863) Absalom(53) had lived,(2416) and all(3605) we had died(4191) this day,(3117) then(227) it had pleased thee well.(5869), (3477)
2Sam. 19:7 - Now(6258) therefore arise,(6965) go forth,(3318) and speak(1696) comfortably(5921), (3820) unto thy servants:(5650) for(3588) I swear(7650) by the LORD,(3068) if(3588) thou go not forth,(369), (3318) there will not(518) tarry(3885) one(376) with(854) thee this night:(3915) and that(2063) will be worse(7489) unto thee than all(4480), (3605) the evil(7451) that(834) befell(935), (5921) thee from thy youth(4480), (5271) until(5704) now.(6258)
2Sam. 19:8 - Then the king(4428) arose,(6965) and sat(3427) in the gate.(8179) And they told(5046) unto all(3605) the people,(5971) saying,(559) Behold,(2009) the king(4428) doth sit(3427) in the gate.(8179) And all(3605) the people(5971) came(935) before(6440) the king:(4428) for Israel(3478) had fled(5127) every man(376) to his tent.(168)
It is worth noting that whatever Joab did, his only purpose was to secure his own interest, and he could only get it from David by showing his loyalty to David and aligned with his interest.
Absalom was killed because Absalom was threatening Joab's interest. If he let go of Absalom and Absalom once again rebelled and succeeded, he would lose everything. David's word in 2 Sam 18:5 showed his weakness as a father to his son, it had happened to Amnon who raped Tamar, that David did nothing; it happened to Absalom who killed Amnon, that David forgave him. David did not kill Saul in two opportunities; David did not kill Abner, the chief commander of his enemies. Joab knew the biggest weakness of David was his kindness to his enemies, even he himself became an enemy of David, he knew he would still live as long as he showed his loyalty to him. But if Absalom became king, he would certainly die.
In the scripture, a solemn oath was when one said "As surely as the Lord lives (NIV)". This oath must be fulfilled. This oath did not find in David's command to Joab, likely because he knew the Lord's judgement was on him, a prophesy given by the prophet Nathan when David killed Uriah and took Bathsheba as his wife.
11 “This is what the Lord says: ‘Out of your own household I am going to bring calamity on you. Before your very eyes I will take your wives and give them to one who is close to you, and he will sleep with your wives in broad daylight.
12 You did it in secret, but I will do this thing in broad daylight before all Israel.’” (2 Samuel 12:11-12 NIV)
It can be seen 2 Samuel 18:5 is a plead rather than a command, for he knew the fate of Absalom was not on him but the Lord. He asked Joab be gentle to Absalom, actually was asking the Lord His kindness to Absalom.
Joab would not know it was the Lord allowed things that happened. He might think it was his opportunity to eliminate his rival without serious consequence.
Joab killed Absalom because he believed David's instruction to spare him was reckless, unjust and extremely detrimental to military discipline. Absalom had committed one of history's greatest treasons - usurping his father's throne, mobilizing the northern tribes to rebel (2 Sam. 15:2,13), and even publicly cavorting with David's concubines on the roof of the royal palace (16:22) after driving David and his loyal troops out of the capital. To cite Joab's own words in explaining his action to David:
Today you have humiliated all your men, who have just saved your life and the lives of your sons and daughters and the lives of your wives and concubines. You love those who hate you and hate those who love you… Now go out and encourage your men. I swear by the Lord that if you don't go out, not a man will be left with you by nightfall. (2 Sam 19:5-7)
This is not to say that Joab acted correctly, only to answer the OP's question. I would add that Joab had a history with Absalom dating back to Absalom's murdering his own half-brother Amnon after David failed to punish Amnon for raping Absalom's sister Tamar. In that case Joab sympathized with Absalom because, once again, he felt David was unjust in administering justice when his own family was concerned. From the New World Encyclopedia article:
Absalom had slain his half-brother Amnon after Amnon had raped Absalom's sister Tamar... For three years, David remains in a state of despondency over the matter. It is not until Joab conspires with a "wise woman" of Tekoa to manipulate David psychologically that the king finally comes to himself and allows Absalom to return. After two more years, with Absalom back in Jerusalem but still banished from the king's presence, it is Joab—under serious pressure from Absalom—who facilitates a reconciliation between them (2 Sam. 15).
Joab apparently saw David's unwillingness to mete out justice within his own family as a fatal flaw. As commander of the troops who were loyal to David, it is plausible that Joab truly believed a mutiny of the army would be the result if Absalom were to be spared. If so, in Joab's mind, killing Absalom was the lesser evil compared to obeying David's command to spare him. In any case, David being completely reliant on Joab to remain in power at this point, Joab knew that David was not in a position to act against him for disobeying a royal command.
Because Joab was a practical politician, as against David who was normally a practical politian but became indulgently sentimental when his own sons were involved.
Once Absalom rebelled against his father, and especially after the public "going in to" David's concubines (2 Samuel ch16 vv20-22), the fight between them was necessarily a fight to the death. Ahithophel understood this, which was why he proposed (2 Samuel ch17 vv1-4) leading a strike force which would take out the fleeing David as quickly as possible.
Why did David ask for Absalom's life to be preserved? Presumably because, as a sentimental father, he had hopes of a reconciliation, after which the forgiven Absalom would be able to live peaceably at court, as after his first return from exile.
Why did Joab kill Absalom? Presumably because, as an experienced politician, he understood that David's sentimental vision would not work. He recognised instinctively that a court containing BOTH a reigning king AND an heir presumptive who had recently tried to overthrow him would be a scene of incredible political tension which would tear the kingdom apart, and probably just the overture to another civil war. He killed Absalom because he was a realist. Machiavelli would have understood.
