גביע is a tall goblet... Since it is written גביע twice, Rashi deduced that it means a tall cup. We need not ask: Why was Yoseif not concerned they would [later] claim the goblet was theirs? Because [the answer is:] It was for divination, so surely it was [not theirs but] Yoseif’s. For it says, “There is no divination amongst Yaakov” (Bamidbar 23:23). (author’s commentary)

May God spare us from doing such a thing... [Implying,] since we have not done it. Re’m asks: On חלילה לך מעשות כדבר הזה (18:25), Onkelos translates חלילה as קושטא (truth). [Why does he translate it here differently?] Re’m answers: [There, it refers to Hashem. And] being “spared” is not applicable to Hashem, since He is not subject to the mercy of others.

This, too, would be only just. Truly it should be as you say... Rashi means as follows: “Your words are now also correct,” does not relate back to [their statement of,] “He among your servants with whom it is found, he shall die.” This is because, “When there are ten persons and a stolen item is found in the possession of one of them,” they all deserve equal punishment [by the king’s law], whatever the punishment may be. That is why Rashi says, “You are all responsible.” Although they had said, “He shall die,” in their bitterness they exaggerated. [Rashi elaborated because] we might think that, “He... shall die,” is what is intended by, “Your words are now also correct.” But this is not so, for [in v. 16, when] the brothers [speak to Yoseif himself, they] do not say this, [that he shall die. Perforce, it was an exaggeration]. Rashi added, “Not according to the strict letter of the law; only he with whom it was found shall be my slave,” because it was not strictly according to the law [to punish only one of them].

Through knowledge, reason ... that you stole the goblet. I.e., although you stole the goblet I divine with, so how could I have known that you stole it? Common sense should have told you that, “A man like me...”

May my words penetrate your ears. [How does Rashi know it does not mean that Yehudah literally requested to whisper in Yoseif’s ear? The answer is:] They spoke to Yoseif only through an interpreter, as they did not know he understood Hebrew. So how could Yehudah speak directly to Yoseif? Another answer: It is not a king’s honor for a lowly person to whisper in his ear. (Re’m)

From this you may infer that he spoke harshly to him. I.e., not gently and politely as one usually speaks to a king. Otherwise, why should Yoseif grow angry?

You are as esteemed in my eyes as a king... From this it follows that “For you are equal to Pharaoh” explains why Yehudah said to him, “Please my master,” by which Yehudah pleaded and supplicated to him, although Yoseif was not a king. Thus Yehudah said [in explanation]: “For you are equal to Pharaoh,” i.e., “You are as esteemed in my eyes as a king.” However, “For you are equal to Pharaoh” does not explain Yehudah’s statement of, “And do not be angry,” which he had previously made. On the contrary, since Yoseif was as esteemed as a king, this is a reason for Yehudah not to speak harshly to him, [so Yoseif’s anger would be justified].

Its Midrashic explanation is: “Ultimately you will be stricken...” [Although the simple meaning is, “You are as esteemed in my eyes as a king”], the Midrash preferred not to say that Yehudah was speaking gently, rather that he was speaking harshly. Thus it explains, “Ultimately you will be stricken...” But there is a question on the Midrash: Why did it not say, “For you will be like Pharaoh”? Thus Rashi offers another explanation: “Just as Pharaoh issues decrees...” I.e., right now you are like Pharaoh. But there is a question regarding this explanation: Why did it not say אתה כפרעה? Thus, both explanations are needed. And there is a question regarding all the [above] explanations: Why did it not say כפרעה כמוך, since Yoseif was being compared to Pharaoh? Thus Rashi offers another explanation: “If you will provoke me...” Now, Pharaoh is compared to Yoseif as regards being killed. But this explanation is implausible on its own because how could Yehudah have said, “Do not be angry,” when he was threatening to kill him? That is why the above explanations are also needed. (Maharshal)

As the Pharaoh was stricken... From this it follows that “For you are equal to Pharaoh” is connected to, “Let your servant speak a word in my master’s ears.” And what is the [harsh] word that I will speak to you? “For you are equal to Pharaoh,” meaning that “ultimately you will be stricken...”

Just as Pharaoh issues decrees without carrying them out... Meaning: Pharaoh wrote in his register that a slave may not rule nor may he wear silk garments, yet he did not carry it out because he made you a ruler though you were a slave. And “he makes promises without fulfilling them,” i.e., if he did not carry out his decree where there is no monetary loss, surely he will not carry out a promise where there is monetary loss. You, too, do the same. You promise and do not fulfill, for is this [the meaning of, “Set your eyes on him?”] “You, too, do the same” does not refer to issuing decrees without carrying them out, for nowhere do we see Yoseif issuing a decree and not carry it out. And nowhere do we see Pharaoh making a promise and not keep it. You might ask: What did Yehudah have against Pharaoh, that he so denigrated the king? The answer is: Yehudah was saying to Yoseif, “On what do you rely? Do you place your trust in Pharaoh [to protect you from our retribution]? Pharaoh himself issues decrees but does not carry them out, as he wrote in Egypt’s laws that a slave may not be a ruler yet he did not carry it out.” (Maharshal)

If you will provoke me I will kill you... From this it follows that “For you are equal to Pharaoh” is connected to, “Do not be angry with your servant,” for if you get angry, I will kill you and your master.

From the start you encountered us with subterfuge. Rashi is answering the question: Why did Yehudah tell Yoseif what Yoseif had spoken to him? Did Yoseif not know what he said? Rashi answers: He repeated it in order to say, “From the start you encountered us with subterfuge.”

Why did you need to ask all these question? Were we seeking your daughter... [Rashi knows this] because only concerning marriage do people ask about sons and daughters and fathers and mothers. You might ask: Why does Rashi say “your daughter” pertaining to Yoseif, and “our sister” pertaining to his brothers, and not the opposite, since the brothers were older than Yoseif? The answer is: Since Yoseif was esteemed in their eyes as a king, they said, “Were we seeking your daughter.” For a son-in-law usually honors his father-in-law. Similarly with, “Were you seeking our sister,” i.e., we would need to treat you with honor so that it will be well with our sister. But the opposite would be a disgrace to Yoseif as a king, for Yoseif would need to honor them.

Nevertheless, “We said to my master” — we withheld nothing from you. Rashi explains this so we will not ask: If Yehudah knew that Yoseif was acting with subterfuge, why did he answer him, “We have an old father...”? Rashi answers: Yehudah was saying, “Nevertheless ... [we acted respectfully and withheld nothing from you].”

He thought, “If I tell him that he is alive, he will say, ‘Bring him to me.’” You might ask: On the contrary, was Yehudah not contradicting himself? When they had come previously to Yoseif, they said he was still alive but had been sold, as it says, “And one is no more” (42:13). The answer is: The first time they came, they said, “And one is no more.” But the second time they came, they were saying that he had died, and this verse pertains to [what they were saying] the second time. Although it is not expressly written that Yoseif asked [now for details] about their lost brother, we can still say that he asked, as we anyway have to say [something similar to] this. It is written here that Yoseif had said to them, “Bring him down to me, that I may set my eyes on him.” But we do not find it written previously that Yoseif had said this to them. Perforce, he must have said it to them although it is not written previously. And the same is true here: the second time they came, when he asked about their father, he inquired also about their lost brother — and they replied that he had died. [They so replied] out of fear. They saw he had told them to bring Binyomin, and perhaps he would tell them to search for the lost brother and bring him. So they replied that after having searched for him, they received word that he had died.

From that mother he has no other brother. I.e., לאמו means “of his mother,” [not “to his mother”]. This is because “to his mother” can be said only if the mother is alive. But after her death, one says that he remains “of his mother.”

He may die en route for his mother, too, died while en route. Question: If it is [as Rashi explains,] why did Yehudah say the danger depended on leaving his father? [According to Rashi,] even if his father would come with him, he should not go, due to the hardships of traveling — as Rochel [his mother] had died in Yaakov’s presence. A further question: Why did Yehudah mention [the factor of] leaving his father, while Yaakov had said (42:4), “Misfortune might befall him” due to the hardships of traveling and the weakness it causes; [see Rashi there]? (Nachalas Yaakov)

As long as he is beside me I find comfort through him. Rashi is answering the question: Why is it written here that on account of Binyomin [Yaakov said], “You will bring my white head down to the grave in evil,” whereas in 37:35 it is written [that Yaakov said] a similar phrase on account of Yoseif? It is written there, “I will go down to the grave mourning for my son [Yoseif].” Rashi answers: Because of Yoseif, they indeed had already brought Yaakov down to the grave in mourning. But now, “As long [as Binyomin is beside me I find comfort through him].” Alternatively, Rashi is answering the question: Why would Yaakov be more sorrowful for Binyomin than for Rochel, Yoseif or Shimon?

Of his mother and his brother. You might ask: How does Rashi know that it refers also to Rochel, when she is not mentioned in the verses? The answer is: It is written (v. 27), “Two sons were born to me by my wife [Rochel].” This conveys, “Two sons were born to me from her, and she is my wife” — i.e., she especially is my wife, [more than Leah]. This is because Yaakov lived mainly with Rochel. This verse implies that he mourned for Rochel but was comforted through Yoseif. And when Yoseif died, leaving Binyomin, he was comforted through him for both. “And if he dies, it will seem to me as if all three died the same day.” But it seems to me that [the answer is:] It is written here, “You will bring my white head down to the grave in evil,” whereas in 42:38 it [merely] is written, “You will bring my white head down to the grave in sorrow.” Accordingly, Yaakov was saying: until now I found comfort for the loss of his mother. But now I will no longer be comforted for her, thus I will go down in evil to the grave. This is because Chazal say (Yevamos 62b): “He who is without a wife is without good.” Consequently, he is with evil. (Maharshal)

By accepting to be outcast in both worlds. You might ask: Rashi said before (43:9) that “I will have sinned to you for all time” meaning in the World to Come. Why does he say here that it means, “In both worlds”? It seems [the answer is:] Here Yehudah is telling [Yoseif] what he said to his father, so it should say מעם אבי לאמר אם לא אביאנו אליך וחטאתי לך כל הימים. [Why does it say וחטאתי לאבי כל הימים?] Perforce, וחטאתי לאבי means in this world, while my father is alive. And [כל הימים means] also in the world that is completely יום, i.e., the World to Come. We need not ask: Why did Yehudah, in order to explain himself, find it necessary to say that he was liable of being an outcast in both worlds, [whereas to Yaakov he spoke only of being an outcast of the World to Come]? For the answer is: He thought Yoseif might not believe in the punishment meted out in the World to Come, so he mentioned also the punishment of this world. But Yaakov believed in the punishment meted out in the World to Come.

I am superior to him for all purposes — in strength... Question: Strength is used for either war or service, and both are mentioned. So why does Rashi need to say “strength”? The answer is: War and service are the explanation of “strength.” In other words, “For what am I strong? For war and service!”