The Torah in Parashat Behar presents the laws that apply on the Yobel, or the "jubilee" year which was observed every fifty years during the times of the Bet Ha’mikdash. One of the laws of the Yobel is that all servants would be released. In those times, men who fell into poverty had the option of selling themselves as servants as a means of sustenance. The Torah commands that servants may not be held indefinitely, and on the Yobel all servants must be released.
Interestingly, when the Torah formulates this command, it emphasizes that with the onset of the jubilee, the servant returns to his family ("Ve’ish El Mishpahto Tashubu" – 25:10). Rather than simply state that the servant is set free, the Torah found it necessary to note that the servant returns to his family.
Contemporary society, to a large extent, views family as a burden that undermines a person’s freedom. To be free, we are trained to think, means being free from responsibilities and obligations, and family life imposes many responsibilities and obligations. The Torah has a fundamentally different understanding of the concept of freedom, teaching that the ultimate freedom is the ability to act the way we are supposed to act – which includes caring for one’s spouse, children, parents, siblings and relatives. We are not to see family as a difficult burden which we begrudgingly bear. We should embrace the challenges and obligations associated with family life, and view them as one of our greatest privileges and among the greatest sources of joy and satisfaction that we can have.
And thus the jubilee, the year of "freedom," is described as a time for families to reunite. The servant does not just go anywhere on the Yobel; he must go back to his family, where he belongs. Family life does not undermine freedom; it is one of the greatest expressions of freedom, and thus the freedom granted by Yobel demands a return to family.