Our Gemara on Amud Aleph discusses the rule that a woman cannot be betrothed by allowing her to keep money she had previously borrowed. This is because the marriage bond needs to be effectuated via a transfer of a tangible object. The loan is not tangible, and even if the money was not spent and thus still tangible, the transfer of money to her domain occurred as a loan, and not an exchange for marriage. A second rule discussed is that if a woman is betrothed with her loan plus an additional peruta, we say she understands and intends to effectuate the marriage via the sole exchange of the peruta, and not the loan.
The Gemara in Sanhedrin (19a) Midrashically explains that King Shaul and David engaged in this very same debate in regard to whether his betrothal to Michal was valid. Michal’s marriage was in exchange for David bringing 100 Philistine foreskins to King Shaul as a kind of dowry, plus King Shaul still owed David the bounty for having slain Goliath. Therefore, King Shaul argued that the marriage was not valid since this was a mixture of a loan and an object of value (the foreskins). But David argued that when a betrothal has a loan and a peruta, it is understood that the intention is to effectuate the marriage via the object of value, and not the loan.
(As an aside, this is an interesting genre of Midrash that projects lomdus back into biblical characters. We discussed this in more detail in Psychology of the Daf Yevamos 96 - was Pharaoh a Lamdan? https://nefesh.org/SimchaFeuerman/was-pharaoh-a-lamdan-yevamos--psychology-of-the-daf-yomi-/read. )
However, there is a problem with this aggadah’s presumption that this halakhic dispute existed during those times. The Yerushalmi (Chagigah 2:2) holds that the first-ever halakhic dispute was in regard to the permissibility of placing hands on a sacrificial animal on Yom Tov, between Shammai and Hillel. The Yerushalmi says that in total, Shammai and Hillel had four halakhic disputes, and only later did the students of Shammai and Hillel develop many more halakhic disputes. This was due to not having fully understood their masters’ fundamental principles, leading to divergent interpretations and applications of the law, which the Elders Shammai and Hillel did not have (Sanhedrin 88b).
If the first dispute occurred during the time of Shammai and Hillel, how could David and King Saul argue about kiddushin with a loan and a peruta? Tosafos (Chagigah 16a, “Yose”) raises this question and answers it by saying it really was not a dispute of legal ramifications since King Saul’s Sanhedrin adjudicated the halakha. According to Tosafos, we can then understand that the idea that there were no disputes prior to Shammai and Hillel does not mean there wasn’t deliberation and discussion. Instead, it meant that various disagreements were expeditiously voted on and resolved by the Sanhedrin. This makes sense, after all, how could an oral Torah be so extensive and precise that every possible contingency was anticipated and legally coded? There had to be questions about application and interpretation from the very moment the word left Moshe’s lips. However, prior to Shammai and Hillel, the Sanhedrin was able to vote on the law and come to a conclusive decision. The Korban HaEdah (Yerushalmi ibid) says this even more explicitly than Tosafos.
This still leaves us with another question. If Sanhedrin had the authority to adjudicate, how is it that in the times of Shammai and Hillel this did not work? I believe we must conclude that though technically the rabbis could vote their opinion, many of them felt indecisive enough that they were reluctant to finalize and close the dispute. I have some evidence in favor of that, as we know that the students of Hillel were generally humble and careful to study the teachings of Shammai as well (Eiruvin 13b). We also know that Shammai’s students were more brash (see Beitzah 20a), and one day, when the students of Shammai were the majority, they “pushed through legislation” and voted on a number of halachos their way (see Mishna Shabbos 1:4). While all of this is supposition, I think we may have a good case for this interpretation of events. Otherwise, why didn’t the students of Hillel overrule the students of Shammai on other sittings of the Sanhedrin? It seems to me that the students of Hillel were more reluctant to convene a vote and rule in their favor, even if they technically could have.
This is an interesting lesson. The students of Hillel much of the time had the power to establish halakha their way, and by definition, the authority of the Sanhedrin would make it so. One could even argue this would have been a good thing to counteract the problem of having Two Torahs, which the Gemara (Sanhedrin 88b) laments. Yet, the humility of the students of Hillel led them to avoid seizing power and forcing their rulings on the students of Shammai, a favor not returned by the students of Shammai.
Translations Courtesy of Sefaria, except when, sometimes, I disagree with the translation 
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