Is there any significance to Yosef's goblet aside from being a prop used to show Yosef's powers and frame the brothers? It seems to be mentioned a lot in the Torah throughout the parsha (especially in Bereishis 44) that it should have some sort of story behind it.
According to the Malbim 44:15 Yosef accuses them of stealing the goblet due to its divination powers . So Yosef makes the claim to the brothers that they are only returning the first money because Yosef has a special goblet he uses to find things out, and now they steal the goblet and the second money so Yosef will not be able to use his goblet to figure it out.
Perhaps Yosef was very purposeful in choosing to scare his brothers with an accusation of stealing his precious goblet. Maybe he was trying to remind them of the time they sold him as a slave. Besides the incredible pain they inflicted on their brother, there was something they didn’t take into account. By separating Yaakov from his favorite son, Yosef, they were also causing the former tremendous grief. But there’s more to it than that.
Yaakov took great efforts to teach Yosef all the Torah knowledge that he knew. The Torah calls1 Yosef Yaakov’s בן זקונים. While it could mean that he was the son of Yaakov’s old age, a זקן also connotes someone filled with wisdom2. בן זקונים would then also mean Yosef was Yaakov’s wise son. This is how we know that Yaakov taught Yosef all that he knew3.
We have many sources4 that compare the Torah to wine. As well, we are taught5 that a teacher learns the most from their students. Students make their teachers wiser. We can then therefore compare a student to a cup, who provides a way for the teacher to drink the wine of Torah. First, the teacher pours the wine into the cup. Meaning, they teach their student the Torah that they know. Subsequently, the teacher drinks the wine, by attaining the wisdom gained from teaching the student.
This was the intention of Yosef placing the goblet in Binyamin’s bag. Yosef’s servants, as they carried out their arrest, declared that this was the goblet that Viceroy Yosef drank from. This hinted to them that they not only stole Yosef’s goblet, but they stole their brother Yosef from their father. Yaakov would pour wine into Yosef, his goblet, as it were, and then would drink the wisdom gained from him. By selling Yosef, they took away this give and take relationship Yaakov was benefiting from.
This could be the intention behind the Aramaic translation of בן זקונים. Targum Onkelos translates6 it as בר חכים, which could be read as a wise son7. However, it seems like it’s causative verb. Meaning, Yosef is someone who makes others wise. This is referring to the wisdom that Yaakov gained by teaching everything he knew to Yosef8.
Yosef had good intentions. He wanted his brothers to be completely atoned for selling him as a slave. While they had their justifications, Yosef felt they hadn’t thought the matter thoroughly through enough. They didn’t realize what they were doing to their father. Not only were they taking away his favorite son, which they surely realized and considered, but they were taking away Yaakov’s main source for wisdom. For that, they needed the hint of the goblet. Only then could they properly repent9.
1 Genesis 37:3
2 Kiddushin 32b; Seder Olam Chapter 30; Toras Kohanim 19:32; Mishneh Torah Hilchos Talmud Torah 6:1
3 Rashi, Ramban, and Targum Onkelos ad. loc. Bereishis Rabbah 84:8. See further for more on the Targum’s understanding. See also Ba’al HaTurim ad. loc.
4 For example, see Proverbs 9:5, Avodah Zarah 35a, and Vayikra Rabbah 30:1
5 Taanis 7a; Makkos 10a
6 Loc. cit.
7 Ramban ad. loc.
8 See Ramban loc. cit. who says that Yaakov taught Yosef סתרי תורה. According to Chagigah 13a, סתרי תורה are only given over to a חכם חרשים, which ibid 14a explains is a student who makes their teacher wise
9 See Be’er Yosef, who explains the double expression נחש ינחש in our verse in a similar vein
Yosef knew that the Jewish people would be in exile for a long time, and that not all of them would possess the same level of Divine consciousness that enabled him to thrive in Egypt. Yosef therefore sought a way of protecting them from Egyptian depravity, ensuring that they would eventually leave Egypt and receive the Torah. Yosef realized that what they needed was a love for G‑d powerful enough to overcome the materialism of Egypt. Yosef’s silver goblet alludes to this love, for the word for “silver” (kesef) is related to the word for “yearning” (kisuf). Yosef further knew that not-yet-fully-righteous people cannot spark such a love by themselves, so he implanted this love in them by “implanting” it within Benjamin. From Chabad.org (based on Ma'amarei Admor HaEmtza'i, Bereishit, p. 297; Or HaTorah, Bereishit, vol. 2, pp. 681 ff, vol. 6, pp. 2208-2209), brought down in "Daily Wisdom". For a more detailed answer, check end of parashah here: https://www.chabad.org/parshah/article_cdo/aid/796363/jewish/Chassidic-Insights.htm#footnote77a796363