But if the creditor said to the debtor: I am lending the money on the condition that I will collect the debt from whomever I wish, i.e., either the debtor or the guarantor, he can collect the debt from the guarantor. Rabban Shimon ben Gamliel says: If the debtor has property of his own, then whether in this case, where the creditor stipulated this condition, or that case, where he did not, he cannot collect the debt from the guarantor.

And so Rabban Shimon ben Gamliel would say: If there is a guarantor for a woman for her marriage contract, from whom the woman can collect payment of her marriage contract instead of collecting it from the husband, and her husband was divorcing her, the husband must take a vow prohibiting himself from deriving any benefit from her, so that he can never remarry her. This precaution is taken lest the couple collude [kenunya] to divorce in order to collect payment of the marriage contract from this guarantor’s property, and then the husband will remarry his wife.

GEMARA: The mishna teaches: One who lends money to another with a guarantor cannot collect the debt from the guarantor. The Gemara at first understands that the mishna is ruling that a guarantor’s commitment is limited to when the debtor dies or flees. What is the reason the guarantor’s commitment is limited? Rabba and Rav Yosef both say that the guarantor can tell the creditor: You gave a man over to me, to take responsibility for him if he dies or flees; I have given a man back to you. The debtor is here before you; take your money from him, and if he has nothing, suffer the loss yourself.

Rav Naḥman objects to this: This is Persian law.

The Gemara interjects: On the contrary, the Persian courts go after the guarantor directly, without even attempting to collect the debt from the debtor himself. Why, then, did Rav Naḥman say that excusing the guarantor from payment is Persian law?

The Gemara clarifies Rav Naḥman’s intent: Rather, Rav Naḥman meant to say that this kind of ruling would be appropriate for the members of a Persian court, who do not give a reason for their statements, but issue rulings by whim. Rav Naḥman was saying that it is not fair or logical to excuse the guarantor and cause a loss to the creditor who was depending on him.

Rather, Rav Naḥman said: What does the mishna mean when it says that the creditor cannot collect the debt from the guarantor? It means that he cannot claim payment from the guarantor at the outset, until after it is established that the debtor has no means to repay the debt. After the borrower defaults, the creditor can collect the debt from the guarantor.

This halakha is also taught in a baraita: One who lends money to another with the assurance of a guarantor cannot claim payment of the debt from the guarantor at the outset, rather, he must first attempt to collect the debt from the debtor. But if the creditor said to the debtor: I am lending the money on the condition that I will collect the debt from whomever I wish, he can claim payment of the debt from the guarantor at the outset, bypassing the debtor.

§ Rav Huna said: From where is it derived that a guarantor becomes obligated to repay a loan he has guaranteed? As it is written that Judah reassured his father concerning the young Benjamin: “I will be his guarantor; of my hand shall you request him” (Genesis 43:9). This teaches that it is possible for one to act as a guarantor that an item will be returned to the giver.

Rav Ḥisda objects to this: This incident involving Benjamin is not a case of a standard guarantor, but a case of an unconditional guarantee, as it is written, also in the context of Benjamin, that Reuben said: “Deliver him into my hand, and I will bring him back to you” (Genesis 42:37). One who undertakes unconditional responsibility for a loan has a different status than a standard guarantor, as will soon be elaborated. Therefore, a biblical source has yet to be adduced to teach that one can become a standard guarantor.

Rather, Rabbi Yitzḥak said that the source is from here: “Take his garment that is surety for a stranger; and hold him in pledge that is surety for an alien woman” (Proverbs 20:16). The verse advises a creditor to take the garment of the debtor’s guarantor as payment for the loan.

And it is stated: “My son, if you have become surety for your neighbor, if you have shaken your hands for a stranger, you have become ensnared by the words of your mouth, you have been caught by the words of your mouth. Do this now, my son, and save yourself, seeing that you have come into the hand of your neighbor: Go, humble yourself [hitrappes], and assemble your neighbors” (Proverbs 6:1–3). This last part of the passage means: If your neighbor’s money is in your possession, as you owe it as a guarantor, open up [hatter] the palm [pissat] of your hand and repay him. And if it is not money that you owe him, but rather “you have become ensnared by the words of your mouth” and owe him an apology for a personal slight, gather together many neighbors through which to seek his forgiveness.

§ Ameimar said: The issue of whether or not a guarantor in fact becomes obligated to repay the loan he has guaranteed is a dispute between Rabbi Yehuda and Rabbi Yosei. According to Rabbi Yosei, who says that a transaction with inconclusive consent [asmakhta] effects acquisition, a guarantor becomes obligated to repay the loan, whereas according to Rabbi Yehuda, who says that an asmakhta does not effect acquisition, a guarantor does not become obligated to repay the loan. Any obligation one undertakes that is dependent on the fulfillment of certain conditions that he does not expect will be fulfilled, in this case the debtor’s default on the loan, is considered an asmakhta.

Rav Ashi said to Ameimar that he was conflating these two issues: But it is a daily occurrence, i.e., it is taken for granted, that an asmakhta does not effect acquisition, and it is also taken for granted that a guarantor becomes obligated to repay the loan he has guaranteed.

Rather, Rav Ashi said: Through that satisfaction that the guarantor feels when the creditor trusts him and loans the money based on his guarantee, the guarantor resolves to obligate himself to repay the loan. Guaranteeing a loan is unlike a usual case of an obligation undertaken that is dependent on the fulfillment of certain conditions that he does not expect will be fulfilled, in which the commitment is not considered a real one. Here, the one obligating himself experiences a sense of satisfaction when the money is loaned to the debtor, and due to that, fully commits to fulfill his obligation.

§ The mishna teaches: But if the creditor said to the debtor: I am lending the money on the condition that I will collect the debt from whomever I wish, he can collect the debt from the guarantor. Rabba bar bar Ḥana says that Rabbi Yoḥanan says: They taught this only when the debtor has no property of his own from which to repay the loan, but if the debtor has property the creditor cannot collect the debt from the guarantor.

The Gemara questions this assertion: But from the fact that the latter clause of the mishna teaches that Rabban Shimon ben Gamliel says: If the debtor has property of his own, then whether in this case, where the creditor stipulated this condition, or that case, where he did not, he cannot collect the debt from the guarantor, by inference one can understand that the first tanna maintains that there is no difference if it is like this and there is no difference if it is like that. Whether or not the debtor has property from which to repay the loan, the creditor can collect the debt from the guarantor.

The Gemara clarifies: The mishna is incomplete and this is what it is teaching: One who lends money to another with the assurance of a guarantor cannot collect the debt from the guarantor before first claiming the debt from the debtor. But if the creditor said to the debtor: I am lending the money on the condition that I will collect the debt from whomever I wish, he can collect the debt from the guarantor. In what case is this statement said? When the debtor has no property of his own from which to repay the debt; but if the debtor has property, the creditor cannot collect the debt from the guarantor. This is the halakha with regard to a standard guarantor, but in the case of an unconditional guarantor, even if the debtor has property of his own, the creditor can collect the debt from the unconditional guarantor.