“The Talmud tells us that the reish also stands for the word rasha, which means an evil person. We know, however, that when a wicked person repents, he becomes a baal teshuvah, and is therefore higher than a tzaddik. In such a case, the reish no longer means rasha, but rosh, or ‘head.’
If you continue drawing the rounded line of the reish (ר), it turns into a kaf (כ), representing the Sefirah of Kesser (crown). In so doing, the reish is elevated to the level of Kesser. This is hinted to by the fact that the reish also stands for rosh (head) and the head’s skull is considered its crown. Furthermore, the numerical equivalent of reish (200) is 10 times kaf (Kesser) (20).
The reish, at times poor and at times wicked, has the ability to do teshuvah. It can awake from its slumber and repent. The reish can truly be transformed into the rosh: the head of the Jewish people.”