The laws governing a Hebrew slave extend far beyond mere legal regulations, revealing a profound layer of compassion for both the impoverished individual and his family. A person's marital status upon entering servitude fundamentally dictates his experience, imposing significant moral and financial responsibilities on his master.
If a man enters servitude alone, his solitary status defines his tenure. The primary approach among commentators understands this solitary entry to mean he arrives with nothing but the clothes on his back [רש״י, שד״ל, רא״ם, רלב״ג]. Alternatively, others suggest the concept refers to his physical state. He enters with a whole, unblemished body and must depart in the exact same condition. This stands in sharp contrast to a Canaanite slave, who is granted immediate freedom if a master knocks out his tooth or blinds his eye [אבן עזרא, חזקוני, תורה תמימה].
Entering servitude as a single man carries a specific restriction: the master is strictly forbidden from giving him a Canaanite maidservant to father slaves [רש״י, רמב״ן, רשב״ם]. There are profound psychological and spiritual reasons for this ban. First, there is a distinct danger that a single man might fall in love with the maidservant and choose to remain in permanent bondage. In contrast, a man already married to an Israelite woman remains tethered to the love of his youth and will not forfeit his freedom for a maidservant [טור, ברטנורא, פענח רזא]. Furthermore, God desires that a person first fulfill the commandment of procreation by raising free, distinguished descendants among the Israelites, rather than bringing children into slavery [לבוש האורה, שד״ל]. While many view this restriction as absolute, some argue that it merely prevents the master from forcing the arrangement; if the single slave willingly desires to marry the maidservant, it is permitted [הכתב והקבלה בשם הריטב״א].
When a man enters servitude already married, the dynamic shifts entirely. Commentators agree that this refers exclusively to an Israelite woman he married prior to his servitude, not a maidservant or a woman legally forbidden to him [רש״י, רא״ם, ברטנורא]. A famous question arises regarding the directive that his wife must leave with him upon his release. Since a woman is never sold into slavery for her husband's theft, why must she be released from a servitude she never entered? The primary approach among commentators is that this directive is not about granting a woman her freedom, but rather establishes a sweeping financial obligation. The purchaser of a married Hebrew slave must feed and support the man's wife and small children throughout the entire duration of his servitude [רש״י, רמב״ן, רבנו בחיי, אור החיים]. The Torah extends extraordinary compassion to a family that has lost its primary provider, essentially commanding the master to step in as a merciful father figure [רמב״ן, טור, חזקוני].
This financial responsibility sparks a debate regarding the master's corresponding rights. One view argues that since the master steps into the husband's shoes to provide support, he is entitled to the earnings of the wife and children as long as they rely on his table [רמב״ן]. Conversely, others maintain that this support is an unconditional act of kindness decreed by the Torah; therefore, the wife retains her own earnings and is under no obligation to work for the master [שד״ל, חומת אנך]. This obligation of support applies strictly to a fully married woman who actively lives with her husband, excluding a betrothed woman or a widow awaiting levirate marriage, as they do not yet depend on the husband's provision [רמב״ן, אור החיים, מלבי״ם]. On a practical level, because the wife and children might live in the master's home and grow accustomed to having their needs comfortably met, a strict boundary is set. When the slave's term ends, the wife must leave with him, even if she prefers the comfort of the master's estate over returning to her husband's poverty [העמק דבר].
Beyond the literal laws, these family dynamics carry deep allegorical meaning. On a mystical level, the relationship mirrors the Israelites and the Divine Presence. When the Israelites are thrust into exile, the Divine Presence, characterized as a devoted wife, goes into exile alongside them. When the time of redemption arrives, she will be the first to emerge with them [פני דוד, חומת אנך]. In another symbolic interpretation, the wife represents the study of Torah. Just as a loyal spouse accompanies a person through life, the Torah a person learns remains with him, ultimately leaving this world alongside him to offer eternal protection [שפתי כהן].