The Tur Shulchan Aruch writes (Orech Chayim 417) that the three pilgrimage festivals, the "Shalosh Regalim," correspond to our three forefathers, Avraham, Yitzchak, and Yaakov. The festival Sukkos, the Tur writes, corresponds specifically to Yaakov. What is the connection?

In Bereshis, we read of the events surrounding Yaakov's encounter with his brother Esav. Although Esav had sold his birthright to his younger brother, Yaakov, Esav was angered when Yitzchak, their father, gave Yaakov the blessings due to the first born. Before this meeting, Yaakov, while on a trip to retrieve some belongings he left at a camp site, had a struggle with the "guardian angel" of Esav. Yaakov, although slightly injured by the angel, came out of the meeting with a blessing. Yaakov then, with trepidation, met with Esav. He emerged from this encounter unscathed, and the two brothers went their separate ways. The Torah then tells us (Bereishis 33:17): "And Yaakov journeyed to Sukkos, and built himself a house, and made booths (sukkos) for his cattle; therefore the name of the place is called Sukkos." Yaakov's construction of "sukkos," booths, for his cattle is the link with the holiday which bears the same name.

Clearly, there must be more of a link between the holiday and Yaakov than just the word "sukkos."

Yaakov, as just mentioned, was on a mission when he had his run-in with Esav's angel. The Talmud (Chullin 91a) explains how Yaakov came to be alone when he met the angel. "Said R. Eleazar: He (Yaakov) remained behind for the sake of some small jars. Hence [it is learnt] that to the righteous their money is dearer than their body; and why is this? Because they do not stretch out their hands to robbery." Yaakov went to fetch some small utensils left behind because he valued these possessions. Why did Yaakov, and according to R' Eleazar, do all the righteous, treasure possessions? Wouldn't we think that the righteous would value the spiritual more than the physical?

The answer lies with the conclusion of R' Eleazar's statement: "They do not stretch out their hand to robbery."

There was a poor man who was scrupulous in his observance of all of the Mitzvos. However, he was so poor that he did not possess a decent cup and basin with which he could wash his hands when it was called for. One night, he dreamt that G-d saw the extent of his penury, his lack of cup and basin, and desire to own one, and G-d then gave him the cup and basin. Upon arising in the morning, lying on the floor next him was the exact same basin and cup which he saw in his dream. This was clearly a gift from G-d, and he treasured it greatly.

The man's fortune changed. He became wealthy, and soon undertook refurbishing his house. Upon the completion of the work, the man made one final inspection of the house. He noticed that his cup and basin were missing. He ordered the workers to search through everything until it was found. They were successful, but perplexed. They had assumed this must be a precious cup and basin, fashioned from silver or the like, and that is why the man was worried about its loss. The cup they found, however, was tin and dented, and they could not fathom why the man was so distressed about the loss. After being questioned about this by the workers, the man had one response: "If G-d Himself had given you something, wouldn't that be the most precious item you possess?!"

It is this attitude, Rav Chaim Vital says, Yaakov and all righteous people share. They appreciate that every item in their possession, all money that comes their way, is theirs because G-d gave it them, to enable them to better serve Him. It is dear, beloved, cherished, and carefully protected. The righteous do not steal. They do not take that which G-d did not give them. They only have that which G-d blessed them with. They know that G-d gave them this gift to enable them to fulfil the precepts contained in His Torah. They therefore value their possessions as one should value a gift from G-d. This is why Yaakov returned to retrieve his small vessels.

Sukkos is a time when we leave our homes and venture outside, into a temporary dwelling, the Sukkah. The Sukkah should remind us that our life in this world is temporary, just as is our dwelling in the Sukkah. Furthermore, the Sukkah should serve to remind us that just as G-d provided for those who lived in the desert with Sukkos to live in, so too does He provide for us. (See YomTov III:20) Yaakov, the Torah tells us, made "sukkos," "huts," for his possessions. For himself, however, he built a home. The Targum Yonasan interprets this not as a literal house, but rather as a House of Study, a "Bais Medrash." Yaakov had his priorities straight. Yaakov valued his possessions for the right reasons. He invested his money in that which has permanence, a house for Torah study. He provided only a temporary shelter for his "temporary" possessions. This temporary shelter is called a Sukkah. Our Sukkah should teach us the same lesson. We must appreciate, right after the conclusion of the High Holidays, our purpose on this earth. We must value our possessions for the same reasons Yaakov did. We must ensure that we understand what the priorities are in our lives. Our Sukkah should remind us of Yaakov's sukkah. Hence, the holiday of Sukkos and Yaakov are indeed inextricably tied, as the Tur stated.

(from Matnas Chaim)