Resources for Kesubos 68
1. The גמרא says that we should be מחזיק טובה to the fraudsters who pretend to be poor for if not for them we would be sinning every day. The מאירי points out that this is not a היתר to not give poor people money and that is exactly why the next line of the גמרא is “ותני כל המעלים עינו מן הצדקה כאילו עובד ע"ז”. What is unclear is what the correct balance is between these two lines of the גמרא. Should you check people out or not? The גמרא in בבא בתרא דף ט׳ says in the name of רב הונא that it depends: if someone asks for food you must give it to him without checking but if he asks for clothes then you should check him out first. The difference between those two is that by food he may not have time for you to check before he has starvation issues while he probably does have time to wait for clothes while you check. A related interesting question is why cant you say to this unknown poor man המוציא מחבירו עליו הראיה? In other words, you should be able to insist that he prove to you that he is actually poor before you give him money. It would seem from the above גמרא in בבא בתרא that you cannot say that and must give him food. However, the ר"ן in נדרים דף ז in ד"ה ולענין הלכתא brings the גמרא in יומא דף ט that says that we don’t need to give מעשר עני from דמאי because המוציא מחבירו עליו הראיה. He proves from there that for all עניני צדקה we don’t consider it איסור where we would say ספק דאורייתא לחומרא but rather as ממון where we would say the owner can claim that the burden of proof is on צדקה. While the שולחן ערוך in סימן רנ"ט סעיף ה is מחמיר (not like the ר"ן) in a case where someone is not sure whether some money they have is צדקה or not, many פּוסקים are מקיל and say he can keep it because of המוציא מחברו עליו הראיה. Nonetheless, our גמרא may be different as the ר"ן is discussing a ספק in regards to specific money, whereas our case is just a ספק on the גברא whether he should give or not and that may be ספק איסורא according to all where you must be מחמיר מספק.
2. The משנה says in the תנא קמא that if a יתומה got married off by her brothers, when she grows up she can demand a dowery of "מה שראוי ליתן לה". Those words are unclear and are the subject of a large מחלוקת ראשונים. רש"י understands it refers to עישור נכסים. רבי יהודה then says that we don’t do that but rather we make an אומדנא of the father’s דעת. Then the חכמים disagree and say we “evaluate the estate and give her”. What does that mean? The fact that רש"י says nothing might lead one to assume that it refers to what was said above in the תנא קמא which is עישור נכסים. תוספות on דף נ ע"ב in ד"ה מאי says explicitly that the חכמים and the תנא קמא are both referring to עישור נכסים. (According to that לכאורה one could ask why the גמרא doesn’t ask תנא קמא היינו חכמים). The ר"ן agrees with תוספות that there are only two opinions but understands the תנא קמא to not exist. In other words, the opening lines of the משנה are simply an introduction. The words of the משנה that say we give her “מה שראוי ליתן לה” are followed by a colon as if to say we will now explain what we meant by “ראוי ליתן לה ". The ריטב"א disagrees and brings a תוספתא that says מפורש that there are three שיטות: the תנא קמא holds עישור נכסים, רבי יהודה holds אומדנא דאב, and the חכמים says we judge what most people with that level estate would give their daughters as a dowery. Interestingly, the תוספתא lists the תנא קמא who says עישור נכסים with a name: רבי himself. We know from our גמרא at the end of the עמוד that רבי only says עישור נכסים when you have no אומדנא, but if you have an אומדנא then you go with the אומדנא (as רבי once gave someone one 1/12th). The ריטב"א proves from this that רבי יהודה must hold that if you don’t have an אומדנא you go like the חכמים or else רבי and רבי יהודה would be the same שיטה. It comes out that when רבא says at the bottom of the עמוד that he paskens like רבי יהודה by אומדנא and that he paskens like רבי where there is no אומדנא, he is really picking a middle שיטה that no תנא holds like. וצ"ע.
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