Just as the counting of the years leads towards the yovel, which clearly relates to the Revelation at Sinai, so does the parallel mitzva of sefirat ha-omer express our anticipation towards Matan Torah. But wherein lies the connection between Matan Torah and the jubilee year?
It is commonly understood, and correctly so, that the period of sefirat ha-omer, which runs from the festival of Pesach until Shavuot, expresses our anticipation of Matan Torah. Indeed, the Sefer ha-Chinukh explains the mitzva of counting tomer as based on the passage in the Midrash that tells of Benei Yisrael's excitement upon learning that God will reveal Himself to them at Sinai. From the day after their departure from Egypt, the people counted the days towards the giving of the Torah. We commemorate this enthusiasm through the counting of the omer.
However, the simple reading of the verses in the Torah regarding the counting of the omer make no mention of this basis for sefirat ha-omer. In Parashat Emor, the Torah introduces the sefira period in a purely agricultural context, as the period in between the beginning of the barley harvest and that of the wheat harvest. The omer offering brought on the second day of Pesach consists of the new barley, whereas on Shavuot we offer the "korban shetei ha-lechem," two loaves baked from the flour ground from the new wheat. These sacrifices mark the agricultural transition that occurs over the course of the sefira period. According to the straightforward reading, then, the counting of the omer expresses the farmer's anticipation towards the completion of the process began on Pesach. Barley (at least in ancient times) is used primarily for animal fodder, while wheat is used in breads and goods eaten by human beings. A successful yield, then, is determined by the wheat harvest rather than the barley harvest. Agriculturally, the counting of the omer signifies the farmer's anxious anticipation towards the culmination of the process that begins with the barley harvest in the early spring.
Chazal, however, understood this anticipation and longing as symbolic of a much deeper, more inherently spiritual yearning: for Matan Torah. Is there any textual basis in the Torah for this association, or does it come to us purely through oral tradition?
Sure enough, we may detect at least an allusion to the Matan Torah aspect of sefirat ha-omer, which can perhaps enhance our understanding and appreciation of the precise nature of this anticipation. The mitzva of counting the omer parallels a different mitzva, that of counting the years with respect to shemita and yovel. As the Torah discusses at the beginning of Parashat Behar, every seventh year is observed as a shemita (sabbatical) year, in which agricultural activity is forbidden. These prohibitions apply as well on the fiftieth, yovel (jubilee) year, which features an additional element: the emancipation of slaves and the return of all real property to its original owner. The High Court is required to count the years leading up to the yovel - seven sets of seven years, parallel to the seven weeks counted annually between Pesach and Shavuot. The Torah calls for the sounding of a shofar on Yom Kippur at the beginning of the yovel year (Vayikra 25:9), which perhaps corresponds to the shofar blast at Sinai (Shemot 19:16). What more, the very term "yovel" - which means "trumpet" - used to describe this fiftieth year refers to this shofar blast, and brings to mind the "yovel" sounded at Sinai (Shemot 19:13). Thus, just as the counting of the years leads towards the yovel, which clearly relates to the Revelation at Sinai, so does the parallel mitzva of sefirat ha-omer express our anticipation towards Matan Torah.
But wherein lies the connection between Matan Torah and the jubilee year?
It would appear that this association alluded to in the text serves as the basis of Chazal's dictum, "ein lekha ben chorin ela mi she-oseik ba-Torah" - a free man is one who occupies himself in Torah. The yovel, the year of freedom and emancipation, is linked with Matan Torah because the latter event reflects the true nature of freedom according to Jewish thought: true freedom is that which allows one to bind himself to God and accept upon himself His laws. Sefirat ha-omer, which bridges the Exodus and the receiving of the Torah, demonstrates that we attained complete freedom not on Pesach, with our departure from Egypt, but on Shavuot, as God suspended Mount Sinai over us and we accepted His Torah. By counting the omer, we show that Pharaoh was not the lone obstacle to religious fulfillment; what was required was the commitment of Sinai, the willful acceptance of God's law and the genuine desire to become His servants.
(Based on a recently published article by Rav Yaakov Medan)