Sefer Chofetz Chaim Chapter 4, halacha 5, note 25-28 and halacha 6

Note 25: Though the Chofetz Chaim said that when the court reprimands a person that committed a severe sin once they should do it in private and in a fashion that won’t embarrass the guy however he elaborated here that if the guy won’t easily listen or if the sin was public and everyone knows about it and might do the same then the Jewish court has a right to take things into their own hands and use him as an example to dissuade others from committing the same thing or give him lashes to be sure he will stop doing the sin himself.

Note 26: Though the court can’t accept one witness’s testimony for it is considered lashon hara if not said with another witness and they don’t have to rebuke the would be sinner, however if they somehow verified that the he did actually sin then they certainly should rebuke him.

Note 27, 28: In the end of the halacha we said that the person who saw someone do a severe sin can tell the sinner’s rabbi or rebbe as long as he believes him like two witnesses and the rabbi is a secretive and modest person who wouldn’t tell anyone else about it. Then the Rabbi can “hate” the sinner for what he did even if you don’t think he will do it again, until he has proven that he has repented then we assume that this type of rabbi when finding out that his student or congregant has repented or he helps him repent will love the repented sinner again and treat like everyone else as he was before the sin. He certainly won’t tell anyone else, which no one should believe him anyways even if he is a trusted rabbi since I’m this is all second hand coming from him and he only trust the guy who saw the sin first hand “like” two witnesses just to be extra cautious and to try to help the sinner mend his ways.

In halacha 6 the Chofetz Chaim says that even if the rabbi is a big talker but if you know if you don’t say anything to him and he is the only person the sinner will listen to them you are allowed to tell the rabbi in order so that the sinner will stop doing the sin if you have indications that he is ready and willing to do the sin again. This is permissible because you are doing this for the sake of Heaven to stop sin in the world. You certainly can’t tell anyone else because you have not actually seen him sin again even if you saw the sin with someone else, to be two witnesses and you know he would do it again, but as long as you have not seen him do it again or really for multiple times he is still included in the verse of “your nation” which one cannot speak lashon hara to anyone about.

Sefer Chofetz Chaim Chapter 4 Halacha 5 part 1 with note 23, 24

If you know the person you saw do an outlandish sin that everyone knows is wrong would not listen to your rebuke because he is foolish and a scoffer, and it’s very possible he will do the sin again then it is permissible to tell the court if you can bring another witness that saw it to testify with him so that the court will privately take the proper initiative to stop him from sinning again. If you are only one witness you can’t tell the court because the Torah says courts only accept to witnesses, one witness constitutes lashon hara since the court can’t believe you. However an individual can go to the sinner’s relatives and tell him what he did assuming they will believe as if he is two witnesses and do something about it. All this is possible because sin disrupts the wellbeing nature of the world and must be minimized as much as possible however one can only tell if he is doing purely for the sake of Heaven, to be zealous for the sake of sanctifying Hashem’s Holy Name in the world but if he has ulterior motives like he has some grudge against the sinner then it will be held against him. Even though he should divulge the information anyway in order to stop the guy from sinning more but Hashem will hold the speaker accountable for his ulterior motives. However one has to be extremely careful before telling a relative, to be sure he will accept what you are saying and try to help because there are many times when relatives don’t believe negative reports about their relatives which can lead to major arguments and fighting that is not worth it for the sake of peace. We see from here that keeping the peace is more important for the world than trying to stop others from sin. One other option is to tell the sinner’s Rav or Rebbe again assuming they will believe you like two witnesses and will keep it private. They are allowed to hate the guy and gently reprimand until he changes his ways.

Sefer Chofetz Chaim chapter 4 part 3 of halacha 4

In terms of a sage who is G-d fearing one certainly cannot divulge to anyone an obvious sin that you saw him do or even think ill of him because without a doubt he realized he did something wrong, had deep bitter remorse and has repented. The Sefer Yad Hakatana goes so far as to say that you cannot even rebuke him which the Chofetz Chaim qualifies that’s only could be true on the day after but there still is a mitzvah even for a student to rebuke his Rebbe respectfully at the time he sees him do something wrong. Also if it was a sin of monetary matters one can rebuke a G-d fearing sage until he gives back the money. However the Chofetz Chaim doesn’t understand why the Yad HaKetana says there is no mitzvah to rebuke because granted we have to judge him favorably but we wouldn’t say he is able to testify as a witness if he would have committed a sin wish would invalidate him from testifying until the judges know for sure that he repented, assuming isn’t enough when it comes to testimony and it assuming should just remove a positive mitzvah of rebuke.

The Chofetz Chaim in his note at the end of halacha 4 says that up until now we are dealing with transgressions that if told to anyone had no ramifications in this day and age. However in a case of a woman who committed adultery one must tell the husband because the husband is forbidden to stay married to her. However you only have a right to tell the husband if you saw the act firsthand not by hearsay. Also you can only tell him if he will believe you like two witnesses and separate himself from his wife. You can’t even tell him who the adulterer is because there is no point in telling the husband, therefore it is lashon hara unless divulging the name will convince him to separate from his wife. Other than that, if the husband won’t listen to you or anyone else then you can’t even tell the court of what you saw because they can’t do anything about it if the husband won’t believe anyone.

Sefer Chofetz Chaim chapter 4, part 2 of halacha 4

The Chofetz Chaim quotes Rabbeinu Yona in his Shaarei Teshuva (219) that a person ideally should not even tell a Jewish court even if he testifies with another witness about someone else’s wrong doing if there is nothing that could be done about it. Rather the one who saw the wrong doing should go over to the transgressor and gently reprimand him in a fashion where it is likely that he will listen to you and try not to commit the sin again. There are circumstances where one should tell a Jewish court of wrongdoing like I’m circumstances where the court can take action to fix the problem, for example a robbery, any other monetary issue or injuries that could be compensated for. However because nowadays the Jewish courts cannot give Torah level lashes or capital punishment then transgresses line incense, or eating pig and shellfish or the like which doesn’t affect anyone else besides sinning against Hashem should certainly not be told to anyone in particular, that would constitute lashon hara/slander but even to inform the courts ideally is not good because we should assume this guy who is a middle of the road guy not necessarily very righteous but not a very bad person who purposely spited G-d, had remorse for his bad deed and hopefully repented. However the Chofetz Chaim does say there is one benefit that could be had by informing the court, in court as official testimony, but not just informing a judge outside of court which is no different than telling anyone else, that is if he did transgress a sin which most Jews no to be wrong then he is invalid to testify as a witness or to swear in court therefore if the court is informed of this person’s misdeeds they know not to accept him as a witness until they know for a fact that he has repented. Other than in court where it is official no one can believe he definitely did the sinful act if they heard about it second hand but they can only suspect misdeed.

Sefer Chofetz Chaim Chapter 4 first part of Halacha 4

 If a person who is not so righteous but not so bad, in the middle, most of the time doing the right thing and you know he did something really bad that everyone knows is a sin, for example he ate non-kosher food like pig or shellfish. Or even if he did a sin not so famous but you warned him not to do it and he did it anyway. You are forbidden to tell anyone what he did because it’s possible he did teshuva and truly regretted what he did. Only if he is constantly transgressing the sin the circumstance might be different and we’ll learn more about that in halacha 7. If you do reveal it to someone else it’s considered a various grievous sin of lashon hara if said behind his back and if said to his face in front of a crowd the person has embarrassed him and therefore might not have any share in the World To Come assuming the sinner did repent. The Chofetz Chaim elaborates in the Be’er Mayim Chaim note 14 that though there is a status in the Torah of someone you are allowed to hate if you saw he did a sin that does not mean you can speak lashon hara because he is still considered part of “your nation” so though he is not considered “your brother” which allows you to hate him as long as you don’t know for sure that he did teshuva since the Chofetz Chaim says that the main part of repentance is regret in one’s heart which only G-d really knows about. But you still have to rebuke anyone part of your nation nicely in private therefore you cannot embarrass and denigrate him in public. If a person does hear lashon hara of this sort he can be cautious but may not accept it as fact, even if two people would tell him unless convicted in official Jewish court. 

Sefer Chofetz Chaim Chapter 4 second half of halacha 2 and Halacha 3

The Chofetz Chaim concluded halacha 2 saying that one can also not speak lashon hara about one who is lacks in even branches of a mitzvah, meaning he keeps part of a mitzvah, for example if a person is frugal with his money and does not honor the Shabbos to the best of his ability like if he can wear nicer clothes for Shabbos or more delicacies at his Shabbos table and just doesn’t do so because he’s too cheap to buy them. You can’t tell anyone this even if you have firsthand knowledge. Also if one is lacks in rabbinic mitzvahs, whether they are fences to stop one from sinning like muktza or decrees like lighting the menora on Chanukah or even if they are seemingly minor rabbinic enactments like how to tie one’s shoe or how to cut your nails, which are both discussed in the Shulchan Aruch, it still constitutes lashon hara to tell others about his wrong doing. However if he doesn’t care about the rabbis and has an attitude that there is no need to keep rabbinic mitzvos then this is a different situation which Rava refers to these type of people as sinners in Shabbos 40a and one who is not only not holy but also an evil person, in Yevamos 20a, in that case there is a mitzvah to speak out against him.

Halacha 3 reiterated that there are a lot of details that must be taken into account when seeing someone do something that he is not supposed to be doing halachically. If he is the average Jew like most of us are who usually is careful about sinning but sometimes transgresses then there is a mitzvah to judge him favorably that he did it unintentionally or didn’t know it is forbidden, or just thought it was a restriction, or nice thing to do which only the righteous are careful in and therefore it is forbidden to tell anyone the sin you saw or heard someone else transgress, even if two people saw it. You can’t even hate him because there is a mitzvah to judge him favorably. There are different halachos in terms of speaking lashon hara and having that person allowed to be a witness. But one has to judge him favorably even if it is a sin people know is a problem, or even assume it was intentional though many people are lacks in the matter, even if the person transgresses it many times. However if he is assumed to be doing a certain sin all the time then the Halacha might change and will be discussed later in halacha 7.

Sefer Chofetz Chaim Chapter 4 first half of Halacha 2

One is forbidden to tell anyone else about sins that other people do or the fact they don’t perform mitzvos, whether referring to sins or mitzvos that everyone knows about or those which people don’t take seriously and don’t understand the severity of the law. He gives two examples of mitzvos not taking seriously, Torah learning and lying. The reason why one cannot tell other that another is lax in these matters even if those listening might not take them seriously is because they will now look at the person being talked about in a different light for now on. The Chofetz Chaim makes a very important differentiation. A person who transgresses a mitzvah out of spite, purposefully not having fear of Hashem is considered “not part of your nation” meaning even if he is biologically Jewish or converted to be Jewish but if he is purposefully rebelling then it is permissible to speak lashon hara about him, but most times than not people just make up excuses of why they do things wrong and a person who just sins or doesn’t do a mitzvah because of some excuse, no matter how lame it is you cannot tell anyone what he did, that would constitute lashon hara in most cases.

There is one Gemara in Bava Basra 111b where it seems that Rebbe Yannai spoke lashon hara about Rebbe Yehuda HaNasi to Rebbe Samlai in front of Rebbe Yehuda HaNasi’s face which might be worse because of embarrassment. Rebbe Yehuda asked Rebbe Yannai a question and Rebbe Yanna told Rebbe Samlai let’s go he really doesn’t want to learn he’s just giving me a hard time. But the Chavas Yair says that a rebbe is allowed to speak harshly to a student in order to motivate him to learn deeper and more diligently which was Rebbe Yannai’s intent in this case therefore it was permissible what he did. Obviously Rebbe Yannai was able to deduce that Rebbe Yehuda Hanasi was able to handle and learn from such rebuke.

Sefer Chofetz Chaim Chapter 4, halacha 1, footnotes 3, 4

Footnote 3: In Brachos 19a it says that if a Tzadik does a sin we assume he immediately did teshuva unless in a case of where he did not return the item he owes the person he took it from. This would seem to preclude that even if a person seems to have changed his ways for the good he is not considered a baal teshuva if he has not returned what he owes. If why does it seem that we are saying here that once we see a person has changed for the good then you can never speak slanderously against him because we can assume he repented, if he didn’t return what he owes he didn’t repent?

The answer is that the Gemara in Brachos and also in Bava Metzi’a 62a which also says, if he relented why does he still have the money, is talking about case where he is able to pay back and he doesn’t then we can technically speak out negatively against him as long as we meet all the prerequisite which will be taught in chapter 10. But here we are talking about a person who didn’t out right steal but rather he was a sleezy, dishonest businessman wheeling and dealing, forcing people to buy or sell things against their will. He became disliked and known by all to be very tough guy to deal with. One day he realized his mistake and changed for the good, becoming an honest businessman man known to all. In this case and in similar cases where it is virtually impossible to return everything he dishonestly took from so many people or he doesn’t have the means to return everything then once he has proven to have completely changed and is now an honest fellow one cannot bring up what he used to do and slander him.

Footnote 4: If one saw someone do a sin he must go over to the guy in private and politely, and gently rebuke him. Only after he repeated his sin in a manner that shows he doesn’t care about the rebuke and about mending his ways than one can publicly embarrass him into repenting.

Sefer Chofetz Chaim perek 4 halacha 1 part 2 of footnote 1 and footnote 2

Two very important lessons we learn today:

        1. People talk, even if they are rabbis and there are far and in between people who are modest and private who you can trust to tell them something and they won’t spread it.

        2. It is illogical to say that if a person did something wrong in his youth even if very severe he still has that problem now, after so many years even if you did not see him repent. If he seems to be acting in a kosher way there is no reason to suspect him of his previous deeds.

Bottom line: People grow up (most of the time)! Therefore there is no excuse to speak lashon hara about them.

Sefer Chofetz Chaim Chapter 4, Halacha 1, footnote 1 part 1

Today we started the 4th chapter of Sefer Chofetz Chaim which discusses speaking lashon hara about deeds a person or his family did of prohibition between man and Hashem, for example breaking Shabbos or not eating kosher. This means one cannot speak out someone or about that person's family that they use to not keep kosher or the like even if they have totally changed there ways and everyone knows that, and even if it is behind his back because if he would be there it is very likely he would be embarrassed if it was brought up. 
It would seem though, that if he was there and he himself brought up the subject about his past, talking about old times and the mistakes he made or just recollecting about good times with his friend at the movies or parties for instance, then it would be permissible for others to continue the conversation and reminisce assuming it won’t damage his reputation or him physically or monetarily and that the person continuing the conversation doesn’t have intent to denigrate him. 
The Chofetz Chaim brought an illustration about how just the fact a person would be embarrassed is reason not to mention his past misdeeds even if it won’t harm him in any way, from a Gemara in Bava Metzia 59a where King David said that anyone who mentions his sin that he did with Batsheva (which was not as severe as it looked, he did complete repentance, and everyone accepted him as king at that time) would still be worse than the sin itself because if anyone would cut him no blood would be spilled, I.e. he is so embarrassed over what happened. All the more so if it will monetarily, or physically harm someone, for example he won’t be able to find a job because of what you said, or even just to scare him is not permissible.  
If done with malicious intent the Rabbeinu Yona says in Shaarei Teshuva 214 that these type of people the Shechina, Divine Presence, does not rest among them. 
The Chofetz Chaim also illustrates how by just not watching what you say one can create severe ramifications. There is a Gemara in Shabbos 33b which relates that Yehuda Ben Geirim  was privy to a conversation the judges in the Sanhedrin about Rome. Rebbe Yehuda was praising Rome for all the useful roads, bridges, bathhouses etc. that were made which could be used by the Jews to serve Hashem better. Rebbe Shimon ben Yochai said they did it all for there own pleasure and sinful ways. Yehuda Ben Geirim went back home and in innocent conversation discussed what he heard in the Sanhedrin that day. Somehow word got out to the Roman government of what Rebbe Shimon Ben Yochai said which had grave results. 
However the Chofetz Chaim did say that one can confide in a righteous person who is known to be modest and private that you can trust won’t say anything else to anyone and know he will not come to judgement about that person being talked about and he is not trying to insult the guy, then you can tell that rabbi about someone, for example who is not eating kosher, or keeping Shabbos appropriately, for maybe he will be able to help him fix his ways. Another application of one you can trust would be a psychologist or the like who is paid to listen to problems and to keep his mouth shut.