The Place of Baalei Teshuvah

Once Rav Levi Yitzchak of Berditchev, zt”l, met a Jewish sinner in the street. To the man’s surprise, Rav Levi Yitzcak grabbed him and lovingly exclaimed, “Do teshuvah and I will be very jealous of your stature. As is well known, you have sinned greatly. But our sages teach that that one who repents out of love transforms his sins to merits. If you change all your sins to merits you will be way ahead of me!”
When the Sifsei Tzaddikim, zt”l, records this story he adds, “It is possible to apply to this the famous gemara that even absolute tzaddikim cannot stand in the place of baalei teshuvah.”
But the Chofetz Chaim, zt”l, once explained this statement differently. “If a tzaddik gives a sinner moral direction the sinner may well think or even say, ‘Easy for him to tell me to change, since he has never tasted the pleasure of the sin he warns about.’
“However, a baal teshuvah who gives moral direction properly is often much more effective. He can say, ‘My precious fellow Jews! I have sinned plenty in my life and I know what it feels like. Nevertheless, I have seen that all sin leads to absolute emptiness. Living a life of sin merely harms one’s soul while affording no true benefit. On the contrary: being shackled to sinful behavior, like heretical thoughts or illicit desires, brings one to depression and ruins his life. Is it any surprise that I decided to let go of such harmful behavior and do teshuvah? I appeal to you, too, to return to the straight path of righteousness.’
“This is why the gemara tell us that a tzaddik cannot stand in the place of baal teshuvah. This means that he cannot be an example to a sinner to change. But a baal teshuvah has a much better chance of standing up as an example to which even a hardened sinner can relate!”