It is well-known that the first modern-day Chief Rabbi of the Land of Israel, HaRav Avraham Yitzchak HaCohen Kook zt"l, engaged very much in kiruv rechokim, outreach to non-observant and even anti-religious Jews. Many of his rabbinical colleagues objected to this approach, because it involves the danger of connecting with and learning from anti-Torah Jews. 

Among those who opposed Rav Kook in this area was Rabbi Yaakov Dovid Wilovsky, known as the Ridvaz, of the cities of Slutzk and Tzfat (Safed). He sent Rav Kook a letter in which he challenged him on his ideas of kiruv, citing the danger of interacting with sinners, among other objections. Rav Kook answered him at length, in his published Letter #555, known as Igeret Takanah (lit., Letter of Rectification; takanah is equivalent to 555 in Jewish numerology). 

Rav Kook wrote to the Ridvaz that there are two aspects of holiness and connection to G-d among the Jewish People. The first is a spiritual inheritance, Israel's spiritual nature, that was passed down to them from the Patriarchs, as alluded to in the verse, "You shall be a special treasure among the other nations" (Sh'mot 19,6). This is represented by a special quality called "segulah," which is an "inner holy force placed in the nature of [our] soul by G-d's will" that is "unalterable." 

The second aspect of sanctity, Rav Kook writes, is a matter of our choice, deeds, and Torah study. The first aspect is "inestimably greater and holier" than the second one, but is revealed nowadays only in proportion to the amount of effort one invests in his deeds, faith, and Torah study. 

Rav Kook continues to explain that there are people whose Jewish segulah is not seen or felt at all, to the point where he could be mistaken for a total Gentile. However, Rav Kook emphasizes, this can only happen to one who has developed a hatred to his Jewish brethren – but that even in this case, his segulah is still there. In our generation, he continues, "there are many souls who, although they are very lowly in their choices and are therefore infected with many bad deeds and very bad philosophies – may G-d save us [from these] – still, the light of the segulah shines in them, and they therefore love Israel very much and yearn for the Land of Israel, and are in fact exceptional in certain precious traits that stem from the segulah of Israel that is in their nature."

Rabbi Kook continues and explains that one who knows how to distinguish between the segulah of a Jew, on the one hand, and the choices he makes in his deeds, on the other, can indeed bring close sinners of Israel. This is because such a person knows how to look only at their inner side, and can consequently cause them to bring out their "choosing" side from within. One who is unable to make this distinction, Rav Kook agrees, should not engage with the sinners, for he is liable to learn from their actions. But those who do see the inner aspects of a Jew, know how to connect only to their deep, holy aspects. 

The Talmud (Tr. Gittin 57a) tells, allegorically, of an interesting encounter between Onkelos, a Roman who ultimately converted to Judaism and authored the famous Targum Onkelos, and Titus, Bil'am, and Jesus (!). He asked each of them in succession if it was worth it for him to convert to Judaism. Each of them acknowledged that Israel holds the most prominent position in the World to Come – yet neither Titus nor Bil'am could find a good word to say about them. Titus advised Onkelos, "If it's honor you want, find a way to torment Israel and that will stand you in good stead with the other nations." Bil'am said, "Don't ever seek Israel's welfare." Jesus, however, said, "Seek Israel's welfare." And the Talmud concludes as follows: 

"Come and see the difference between the sinners of Israel [Jesus, in this case] and the prophets of the idol-worshipers" – in that Jesus found good things to say about Israel. The Talmud points out that even when a sinner seeks to incite people to go against G-d and His Torah, he still retains an inner spark of sanctity – and this is why he still spoke highly of Israel. Whereas Titus and Bil'am knew the truth, and knew what is important, yet they were simply unable to come close to Israel and see their good side, because of their great hatred and desire for evil. 

A sinner of Israel, on the other hand, still bears within him an inner point of connection with the People of Israel – and even though he was a renegade, he still said to Onkelos, "Seek their goodness."

Yes, there are Jews who have lost their segulah altogether, Rav Kook admits, "and regarding them, King David writes: 'Those who hate You, I will hate' (Psalms 139,21). In general, our Sages gave us signs by which to recognize them… But regarding this generation of the Footsteps of Messiah, the Zohar tells us that it is 'good within and bad on the outside.' [This is expressed in the concepts of] the Messiah's donkey, about which we learn that the Messiah might come as a poor man riding on it. The idea behind it is this: A donkey is a non-kosher animal with two external signs of its impurity (no split hoof and no chewing of its cud), rendering it seemingly "more non-kosher" than either a pig or a camel, which only have one such sign each. However, in fact, the donkey has an inner sanctity, manifest in the mitzvah of redeeming a first-born donkey, the likes of which does not exist with the pig or camel. [This shows that the external sides are not necessarily the determining factor.]" 

The conclusion from all of the above is that the Nation of Israel, in every situation, will always be connected to G-d. Even when they do not behave correctly, they are called His children, as the Sages teach. In our generation, unfortunately, many Jews do not behave in accordance with the Torah's standards – yet this does not detract a bit from their inner spark of Jewish holiness, and we must relate to them accordingly. Our job is to actualize this inner potential, to the point where it will be clearly seen by all that the Jewish People are G-d's nation, "Israel, in whom I take pride" (Isaiah 49,3). 
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