Is it better, if one is going to gamble or do other shady ethical activity (and yes, I know it is better not to do it at all, but whatever), to remove signs of Jewishness like a Magen David or a kippa before? Or is that worse?
Let me start by agreeing with you that it is better not to do any such activities at all-- one nice rubric is that if we are about to engage in an activity where we think we might need to remove our signs of Jewishness, that is probably an activity to avoid. Granted, sadly, that we all do things we should not, and we're not always ready to forego them, this is still a hard question. If, by removing the identifying sign, the people around me will no longer realize I am Jewish (including, perhaps, other Jews in the room), there is room to argue that it is better to do so, to avoid the marit ayin aspect of the activity, the worry that other Jews will see my actions and assume that there is something ok about them. So, for others, it might be better. On the other hand, for yourself, there is still and always the hope that this reminder will at some point become so intrusive as to get you to listen to your better angels, as it were.
The Talmud tells a story that well illustrates both sides of your quandary. He was not, in fact, a rabbi or a scholar,but he was careful about the mitsvah of tsitsit. One time, he heard of a remarkable prostitute who charged (and received exorbitant fees). Certain that this would be an experience he could not forego, he went to her, paid the fee, and was disrobing, when he encountered his tsitsit, and realized he could not go through with it. She became very upset, demanded that he tell her what was wrong with her, and he explained that it wasn't her, it was him (his tsitsit, anyway). She insists that he give her his information, where he lived, etc. [Then the story goes on, that she sells everything, gives most of it to the government and charity, and converts so she can marry him, but that's a different part of the story]. Notice, though, that he goes to somewhere where no one knows him in order to sin-- which the Talmud elsewhere seems to recommend, both to avoid others seeing him sin, and in the hope that it will encourage him to get control of himself.
So, I hope for all of us that we don't act in ways we think of as inappropriate. When we do, I hope we keep in mind that we do not stand only for ourselves, but for a whole people. And if we feel that we are such bad examples of that people, right then, I hope that as we try to remove our distinguishing signs, that those signs themselves remind us who we are, and help us get back to being what we might be.
Let me start by saying that I agree with you that if there is something that we feel we shouldn’t be doing, then that should be enough not to do it. But given that human nature and our yetzer harah (our evil inclination) sometimes wins out, your question about how best to identify ourselves when we engage in something we probably shouldn’t be doing anyway, is a good one.
Although I appreciate your use of gambling as an example, it seems to make more sense to address the category of “shady ethical activity.” I say this because in terms of gambling there is obviously a big difference between trying a nickel slot machine (silly but harmless) on a vacation and betting on a dog fight (which you should not do, kippah or not!). Therefore, it is not gambling as a general category that I want to address, but the secondary implications. Is a shady activity one that is legal or not? How do you behave while doing that activity? What language do you use? How do you treat others? In my opinion, all of these questions, and others like it, play a role in whether or not you should wear a kippah
So in answering the question I would like to focus on the role of a kippah. A kippah is worn to remind yourself of God’s presence (an act of piety) and/or to identify yourself to others as a Jew who believes in Jewish values and tradition. With that in mind, I believe you should remove your kippah (and other signs of Jewish identity) if you are doing things that are “shady.” However, this only addresses the second role of the kippah. In the first role, removing the kippah will not remove Gods presence or make you invisible. That of course is between you and God. As for the second issue which relates to your fellow human being, the kippah should be removed because for reasons that can be explained with the introduction of two religious categories.
The first is maarit ayin-giving the appearance that something is permitted “Jewishly” even if it is not. As stated above, when you wear a kippah people look at you as a Jew who knows what they are doing, and if you are doing it then, it must be “kosher.” You have a responsibility to not mislead people in this way. The second category is chilul ha’shem literally the desecration of God’s name, implying that you, through your activities, create a bad reputation for the Jewish community because one would say look at the Jews they all do (insert “shady ethical activity here). This is the reason Jews cringe when they see a Jew in the news doing something bad. Therefore, if you can’t help but engage in “shady ethical activity” you should remove the kippah.
Finally, your very question shows the power of the kippah and perhaps its third role. Simply wearing creates an entire thought process before you take on any action. These questions are hopefully a buffer between you and shady activities.
Gambling is legal in many states and in countries all over Europe. If you think gambling is shady, do not do it. Wearing or not wearing a Magen David is irrelevant. I am reminded of the time my son was chasised for wearing his Kippah while having a cup of coffee in MacDonald’s. The self righteous chastiser said, “Someone seeing you there might think that MacDonald’s is kosher”. This is ludicrous.
The premise of maarit ayin applies to acts that might be thought of as violations of halachah. An example might be a known orthodox person eating roast beef and Imo (a vegetable imitation of sour cream) in public.
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