Haggadah-Mix of Slavery & Freedom
A thief watched a clerk every day as he carried bags of money for deposit in a bank. He went in to a clothing store and said, “I wish to order an expensive suit of clothes for an out-of-town friend. I shall watch for a man of his build and shall ask him to allow you to fit the garment according to his size.”
When the clerk past by with his money for deposit, the thief approached him and promised to pay him if he would step in for a moment to have his measurements taken. The clerk agreed, and while he was being fitted, the thief seized the bags of money and started to run away.
The clerk wanted to pursue him, but the tailor said, “First take off this expensive suit which belongs to me, and then you can run after him.” In the meantime, of course, the thief had disappeared.
From this we learn that the soul of man is eager to ascend to Heaven, but Satan has placed on him the garments of worldly desires. The Guardians of Paradise therefore say to the soul, “Remove the foreign garments you are wearing before you ascend to Heaven.” (Dubner Maggid)
We act out many elements of suffering and slavery so that we can shed those garments and dress ourselves in the clothes of freedom.