The Most Difficult Thing
"Should you buy a Hebrew slave..." (Exodus 21:2). The laws of Mishpatim begin with the slave, because there is nothing more difficult for a person than to be submissive and enslaved to another. (Ibn Ezra)
Concern for the Servant
The section of Mishpatim begins with the law of the Hebrew slave to warn the judge not to trivialize the slave’s case, not to delay judgment, and not to prioritize other Torah laws or civil matters, thinking that they are more important than the slave’s case. (Iturei Torah)
A Servant Already
Why does it say, “Should you buy a Hebrew slave,” if he only becomes a slave after the purchase and was not bought as one? There is here a hint to the buyer: know that you are purchasing a slave, a person who is already a slave to another Master—the Master of the Universe. (Alsheich)
Levels Among Servants
A “Canaanite slave” is a person whose natural inclination is toward worldly desires, but who restrains himself and does not succumb to them, through acceptance of G-d’s yoke. In contrast, a “Hebrew slave” is one whose Divine soul illuminates his heart, filled with love for G-d, and who does not desire to remove the yoke. (Tzemach Tzedek, Derech Mitzvotecha)
