עז פנים לגיהנם ובושת פנים לגן עדן (אבות ה:כ)

The son-in-law of the Chofetz Chaim served as the Mashgiach of Yeshivas Radin. Once, he sought advice from the Chofetz Chaim regarding a refined bochur (yeshiva student) who had neglected proper prayer for some time. He asked whether the student should be allowed to remain in the Yeshiva.

The Chofetz Chaim responded reassuringly, “It’s not a big deal, don’t worry. This young man will grow up to be a Rav,” indeed, that prediction came true.

Later, the Mashgiach approached the Chofetz Chaim with another matter. A student who was living with a widower in challenging conditions had begun speaking disrespectfully to the widower, albeit under difficult circumstances. The Chofetz Chaim was displeased with the student’s behavior and advised him to be sent away from the Yeshiva.

He explained his reasoning when the son-in-law questioned why the Chofetz Chaim had made different decisions in these two cases. “There’s a famous Mishna that says, ‘עז פנים לגיהנם ובושת פנים לגן עדן’ – someone who is brazen-faced has no chance of repentance, but someone modest will indeed repent!”