On a biblical level a yavama becomes the wife of the yabam only though yibum, and a yavama is only free to marry anyone else through chalitza. We have discussed previously that the Chachamim instituted that a maamar is required prior to yibum, much like kidushin precedes nissuin. The maamar resembles kidushin in that it is performed either with an object value or through a contract. The Chachamim were also concerned and decreed that if the yabam gave the yavama a get (divorce document) then it would have an effect. Chalitza would still be required, but no further yibum can be performed.
The fifth perek opens with a debate whether a maamar followed by a maamar or a get after a get in the context of yibum is effective. Rabban Gamliel argues that is not while the Chachamim maintain that they are. The Bartenura, when presenting the position of Rabban Gamliel explains that if there were two yevamot and one yabam and he gave a get to both, according to Rabban Gamliel the second get would not be significant such that he would be able to marry the second yavama's relatives. Similarly, in a case where there are two yevamot and one yabam and he performed a maamer to both, or if there were two yabamim and one yevama and they both performed a maamar, the second maamar is not effective and a get (to undo that maamar) is not required.
The Rishonim1 however question why Rabban Gamliel maintains that a maamar after a maamar is ineffective. In a case where there are two yevamot, and yibum has been performed to one, the brothers are indeed prohibited to marry the tzara (second yevama). However the relationship is not punishable with caret; as would normally be the case for one's brother's wife. Instead it would constitute a "regular" negative prohibition (lav). According to the Chachamim, kidushin with one that is prohibited by way of a lav is binding and they would be married despite the violation. Consequently, if performing kidushin to the tzara after yibum is effective, then in our case we should treat the maamar as kidushin and it should be binding even after the (first) maamar. Why then does Rabban Gamliel maintain that there is no maamar after a maamar?
One answer is that Rabban Gamliel's ruling in the Mishnah is according to the position of R' Akiva who maintains that kidushin is not binding in a relationship that is prohibited by way of a lav. Consequently, in the above case, kidushin to the tzara would not be binding and does not present a difficulty for Rabban Gamliel. Why does the Gemara not comment that Rabban Gamliel rules like R' Akiva? One answers is that the Chachamim argue with this position in the Mishnah. The Gemara only comments that the Mishnah is to be interpreted according to one opinion when the position in the Mishnah is not argued against. Alternatively, it is because Rabban Gamliel does not maintain the position of R' Akiva in general.
The Ritva and Tosfot find this answer difficult. Instead they maintain that the position of Rabban Gamliel can be understood to be consistent with the opinion of the Chachamim that maintain that kidushin is binding despite an issur lav. They explain that kidushin is only binding when we consider kidushin that is biblical in nature. In the other case, after yibum is performed to one of the yevamot, there is no longer a zika (obligation to perform yibum or chalitza). Consequently, the act of kidushin to the tzara is biblical. In our case however, after the first maamar there is still a zika. Consequently, even though the act at that point may resemble kidushin, it at best can only be considered a maamar which has rabbinic force. According to Rabban Gamliel however, the Chachamim only instituted one maamar. Therefore, any additional maamar according to Rabban Gamiel is meaningless.
1 This question along with both answers are found in the Tosfot, Ramban, Rashba and Ritva.
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