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As we know, Yakov was 100% sure that Yosef was alive when he saw the wagons that Yosef sent. Rashi there explains that the wagons , Agola, are the same words as Eglah (as in Egla Arufa) and that was the last topic Yosef and Yaakov were learning when he disappeared.
I'm curious how did Yakov know that the wagons were a sign for egla arufa? Was it just word association in that a Calf and Wagon both use the same words? Who thinks like that? Was it more than that?
Rashi doesn't say that Yaakov figured it out from seeing the wagons. What he says is:
סימן מסר להם במה היה עוסק כשפירש ממנו בפרשת עגלה ערופה זהו שאמר וירא את העגלות אשר שלח יוסף ולא אמר אשר שלח פרעה
He gave them a sign – with what had he been engaged when he separated from him? With the topic of eglah arufah. This is what it says "and he saw the wagons that Yosef sent", and it does not say that Pharaoh sent.
It says that he gave them a sign. It sounds like Yosef gave the brothers a sign, namely the last topic he had studied with Yaakov, and the brothers presented that to Yaakov. In this case, Yaakov didn't need to make any connections; it was all spelled out for him.
This is even more clear in the Midrash from which Rashi's comments derive:
ר' לוי בשם ר' יוחנן בר שאול אמר להם אם יאמין לכם הרי מוטב ואם לאו אתם אומרים לו בשעה שפרשתי ממך לא בפרשת עגלה ערופה הייתי עוסק הה"ד וירא את העגלות ותחי רוח
R. Levi in the name of R. Yochanan Bar Shaul – he said to them: "If he believes you, fine. But if not, you should tell him that at the time that I separated from you was I not engaged in the topic of eglah arufah?" That is what is written "and he saw the wagons and his spirit was restored".
According to this Yosef explicitly told the brothers about the last topic he had studied, and he told them to furnish that as proof that Yosef was alive. There was thus no "hint", and Yaakov didn't have to guess anything. It presumably didn't have anything to do with the actual wagons that Yosef sent. The point about the common word seems to be for the readers. The Torah is telling us that not only did Yosef send physical wagons, he also sent another form of agalot, namely the report about his last study topic being eglah arufah, and when Yaakov heard that he was convinced that Yosef was still alive.
Rabbi Weinreb discusses the question and asks what is is about egla arufa that causes Rashi to make the connection to the wagons. Is it only a word play and what would be the message that Yosef is trying to convey?
Rabbi Weinreb explains that the message that Yoseph conveyed with these wagons was that he had learned the lesson of personal responsibility for everything that he was involved in. The meforshim explain that Yaakov saw that Yosef had not just sent the wagons of Par'o to get them (from the markings on the wagons) but had ensured that the symbold of avodas zarah had been removed from them. Had he just ordered wagons from Par'o's stables, the normal avodas zarah marking would have been left on. It was the complete setup of the wagons that showed Yaakov that Yosef had been personally involved with sending them.
Rashi wonders what it was about the wagons, the agalot, that convinced Jacob and revived his spirit. Rashi tells us that these wagons were a sign sent by Joseph to Jacob, recalling the subject of their learned conversation when they first parted ways so long ago.
That subject is the ritual of the “calf [Hebrew egla] with a broken neck,” the details of which are described in the first several verses of Deuteronomy 21. Joseph was apparently confident that Jacob would see the connection between the word for wagons, agalot, and the word for calf, egla.
The reader of Rashi’s words cannot help but ask with astonishment: Is this some game, some bizarre wordplay? Agala calls to mind egla? What connection can there be between the ritual of the calf and Jacob’s parting words of instruction to Joseph before sending him off on his mission to his brothers, never to see him again until this moment?
...
As the Kli Yakar explains, if the elders of the city are not hospitable to the wayfarers who frequent the city, the criminals who populate the environs of the city will assume that this wayfarer is of no import, and they will therefore take liberties with him, even to the point of shedding his blood. Were these villains to observe that the wayfarer was significant enough to the elders of the city to be treated graciously, they would have refrained from harming him.
This is the nature of responsibility. The elders are not suspected of actual murder. But if they treat their guests improperly, they set in motion a process by which those guests are dehumanized, becoming easy prey to malicious persons. That is how far the demands of responsibility extend.
When Jacob sent Joseph on his dangerous mission, continues Kli Yakar, he escorted Joseph part of the way. By doing so, he was teaching Joseph the lesson of the “calf with a broken neck,” the lesson of the importance of escorting the traveler, thus demonstrating the human value of that traveler. Joseph signaled to his father that he learned that lesson well and knew the responsibility entailed in dealing with one’s fellow.
Jacob realized that it was Joseph who personally had a hand in sending the wagons of Pharaoh, thereby escorting his brothers part of the way back to Canaan. Jacob took note of those wagons and therefore knew that Joseph had learned that a minor gesture of considerate behavior to others may have long-term consequences. He signaled that he had learned the crucial importance of taking responsibility for all one’s actions, however insignificant they may appear. And so, “The spirit of their father Jacob revived.”
Agalot and egla are not just words in a linguistic game. Rather, they allude to the profound lesson about personal responsibility, which is the basis of the requirement of the elders to proclaim their innocence of murder.
The Pshat of the words are that although at first Yaacov didn't believe that Yosef was still alive and even a ruler, he saw many wagons arrive that did not originate from him and were obviously being sent from elsewhere. This opened his mind to the idea and he let it sink in.
Chazal are saying that in these words Agalos there is a hint to something else that transpired, that in addition to having sent the wagons he also sent along this message of Egla Arufa.
Rashi's wording supports this understanding, that the Remez is that he sent a verbal message.
In addition we can understand this that the wagons, being called Agalos, served as a reminder of Egla Arufa rather than a hint. Yaakov had escorted Yosef and he therefore should understand that it stands to reason, and he should allow himself to believe, that nothing bad happened to Yosef (in the long run).
An idea i once heard, similar to IsaacKotlicky, is that the Egyptians invented the wagon and would not have let it out, which is why we find that Yosef had to have Paaroh's permission to send them. Up until this point we only find mention of carrying things on camel back. This is why Eliezer needed ten camels. Therefore, the wagons were both, a hint and a sign that someone with high connections had sent them.
