What does 2 Samuel 15:20 mean?
ESV: You came only yesterday, and shall I today make you wander about with us, since I go I know not where? Go back and take your brothers with you, and may the Lord show steadfast love and faithfulness to you."
NIV: You came only yesterday. And today shall I make you wander about with us, when I do not know where I am going? Go back, and take your people with you. May the Lord show you kindness and faithfulness."
NASB: You came only yesterday, so should I make you wander with us today, while I go wherever I go? Return and take your brothers back; mercy and truth be with you.'
CSB: Besides, you only arrived yesterday; should I make you wander around with us today while I go wherever I can? Go back and take your brothers with you. May the Lord show you kindness and faithfulness."
NLT: You arrived only recently, and should I force you today to wander with us? I don’t even know where we will go. Go on back and take your kinsmen with you, and may the Lord show you his unfailing love and faithfulness. '
KJV: Whereas thou camest but yesterday, should I this day make thee go up and down with us? seeing I go whither I may, return thou, and take back thy brethren: mercy and truth be with thee.
NKJV: In fact, you came only yesterday. Should I make you wander up and down with us today, since I go I know not where? Return, and take your brethren back. Mercy and truth be with you.”
Verse Commentary:
History repeatedly shows that enemies in one war can become allies in the next. The soldiers you fight against in one battle may become lifelong friends when peace is called. In David's early years, he built his reputation on killing Philistines (1 Samuel 18). When King Saul wanted him dead and he had 600 men and their families to protect, David found that protection with Achish, the Philistine king of Gath (1 Samuel 27). Once he became king, the Philistines attacked, and David conquered them and Gath (1 Chronicles 18:1).

We don't know how Ittai, his 600 fighting men, and their families came to work for David, but it was very recent. It was almost certainly not literally the day propr. The point is that Ittai hasn't been there long enough for David to expect any kind of loyalty. David's son Absalom is marching to Jerusalem. David must take his servants and flee or risk a war he's not prepared for in the city he loves (2 Samuel 15:13–19). Ittai and his people don't deserve to have to pack up again so soon.

So, David urges Ittai to stay, to be loyal to the king of Israel, not the man David. He wishes the Philistines God's "steadfast love": hesed. Absalom's betrayal is part of God's judgment on David for sinning against Uriah (2 Samuel 12:11). David doesn't know if he's going to survive this fight. Absalom would certainly welcome 600 fighters. And, as he takes Jerusalem, he'll have the money to pay for them.

Ittai takes an oath on the name of the same God by which David offers a blessing (2 Samuel 15:21). David accepts his vow. Ittai makes good on his promise. He joins David's nephews, Joab and Abishai, as commanders of what's left of David's army. They defeat Absalom and his army and make sure David remains king (2 Samuel 18).
Verse Context:
Second Samuel 15:18–23 recounts how some Gentiles were even more loyal to David than his fellow Israelites. David's son Absalom is marching toward Jerusalem, intent on taking the throne. David and his household are fleeing the city. With them are three Philistine military units who serve David. Even after David urges them to avoid the inevitable war and go home, they stay with him. Much of David's army stays with Absalom (2 Samuel 17:25). Farther on, David will encourage the priests, their sons, and his advisor to stay. He trusts them to either foil Absalom's plans or send warning (2 Samuel 15:24–37).
Chapter Summary:
God's curses against David continue (2 Samuel 12:10–12). David's son Absalom stages a coup. His followers declare him king and escort him to Jerusalem. David and those faithful to him flee the city for the wilderness. He leaves behind two priests, their sons, and an advisor to thwart Absalom's plans. As he travels, David willingly endures every humiliation, not knowing which are from God. Joab kills Absalom, and the kingdom is restored (2 Samuel 16—18). Absalom's betrayal is not recorded in 1 Chronicles.
Chapter Context:
Second Samuel 15 continues the fulfillment of God's curse on David. As he betrayed his friend Uriah, so someone from David's house will betray him (2 Samuel 12:11). David's son Absalom steals the people's hearts and declares himself king. David and his household flee the city, leaving behind ten concubines and five spies. The spies protect David until Joab can kill Absalom in battle. David is humbled and forgives his enemies (2 Samuel 16—19).
Book Summary:
Second Samuel continues the story of David, who will become king over Judah. The other tribes of Israel are resistant, eventually sparking a civil war. David wins and makes Jerusalem his capital. Early success is followed by moral failure and controversy in David's house. The book of 1 Kings will begin by detailing David's decline and death.
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