‘And the lords of the Philistines came up to her, and said to her, “Entice him and discover in what his great strength lies, and by what means we may prevail against him, so that we may bind him to afflict him. And we will each one of us give you eleven hundred pieces of silver.” '
Probably the destruction of the gates of Gaza had been the last straw. If he could do that nowhere was safe. So the five Tyrants of the Philistines were probably initially determined to kill him. But they put it more gently to Delilah as though they only wanted to punish him. They did not want it to appear unpalatable to her.
Although he was a powerfully made man they recognised that there was some extra secret to his amazing strength and they wanted to discover it. Then they would be able to overcome him and do what they wished with him. So they offered her five thousand five hundred pieces of silver in return for the secret. This was a huge sum. (Ten pieces of silver was a year's wage for the Levite who was being enticed to act as a priest for Micah - Judges 17:10). It demonstrated how seriously they saw him as a threat. And she was probably impressed by, and fearful at, the presence of these five hugely important men. It is possible, however, that they sent five lesser representatives, but even they would have been seen as important men by Delilah.
“Entice him.” As men themselves they knew the impact of a beautiful woman and what she could learn from a man, especially in bed.