Why did Jacob weep?
וַיִּשַּׁ֥ק יַעֲקֹ֖ב לְרָחֵ֑ל וַיִּשָּׂ֥א אֶת־קֹל֖וֹ וַיֵּֽבְךְּ׃
Then Jacob kissed Rachel, and broke into tears.
ויבך. לְפִי שֶׁצָּפָה בְרוּח הַקֹּדֶש שֶאֵינָהּ נִכְנֶסֶת עִמּוֹ לִקְבוּרָה. דָּ"אַ לְפִי שֶׁבָּא בְּיָדַיִם רֵקָנִיּוֹת; אָמַר, אֱלִיעֶזֶר עֶבֶד אֲבִי אַבָּא הָיוּ בְיָדָיו נְזָמִים וּצְמִידִים וּמִגְדָּנוֹת וַאֲנִי אֵין בְּיָדִי כְלוּם; לְפִי שֶׁרָדַף אֶלִיפַז בֶּן עֵשָׂו בְּמִצְוַת אָבִיו אַחֲרָיו לְהָרְגוֹ וְהִשִּׂיגוֹ, וּלְפִי שֶׁגָּדַל אֶלִיפַז בְּחֵיקוֹ שֶׁל יִצְחָק, מָשַׁךְ יָדָיו. אָמַר לוֹ מָה אֱעֱשֶׂה לַצִּוּוּי שֶׁל אַבָּא? אָמַר לוֹ יַעֲקֹב טֹל מַה שֶּׁבְּיָדִי, וְהֶעָנִי חָשׁוּב כַּמֵּת:
ויבך AND HE WEPT- because he foresaw by the Holy Spirit that she would not be buried with him in the cave of Machpelah (Genesis Rabbah 70:12). Another explanation is: he wept because he came with empty hands. He thought: Eliezer, my grandfather’s servant, had with him rings, bracelets and all good things, whilst I have nothing with me (Genesis Rabbah 70:12). This was because Eliphaz Esau’s son pursued Jacob by his father’s order to kill him, and overtook him. But because Eliphaz had been brought up on Isaac’s lap, (cp. Deuteronomy Rabbah 2:13) he withheld his hand. He said to him (Jacob), “But what shall I do as regards my father’s order?” Jacob replied, “Take all I have and you can say that I am dead for a poor man may be accounted as dead" (Nedarim 64b).
וישא את קולו ויבך על שלא זכה לשאת אותה בנעוריו והיו לו לעת כזאת בני נעורים:
And cried in a loud voice. He was pained that he did not merit marrying her in his youth so that by now he would have had grown up children.
ויבך, זו היא בכיה של שמחה ומרוב אהבה המית הלב:
ויבך, he wept for joy. When close relatives meet after not having seen each other for a while, their emotional cup runs over so that they find it hard to control their feelings and they give way to them by crying for joy.
לפי שצפה ברוח הקודש שאינה נכנסת עמו לקבורה. ולהאי טעמא קשה באם שהיתה אומרת לו למה אתה בוכה בודאי לא הזכיר לה מיתתה וא"כ מה השיב לה לכן פירש ד"א ולד"א לחוד קשה איך צדיק כזה יבכה על חסרון ממון. [מהרש"ל]:
Because he foresaw... she would not be buried with him. There is a question on this explanation: If she would ask him, “Why are you crying?” he surely would not mention her death to her. What would he answer? Therefore Rashi brings another explanation. And with the second explanation alone, a question arises: Why would this great tzaddik cry because he came empty-handed? (Maharshal)