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

The son-in-law of the Chofetz Chaim was the Mashgiach of Yeshivas Radin.  He once asked the Chofetz Chaim for advice on how to deal with a refined bocher who wasn’t davening appropriately for a while – should we allow him to remain in Yeshiva or not?  

The Chofetz Chaim answered, “It’s not a big deal, don’t worry, this bocher will grow up to be a Rav,” and so it occurred.

The Mashgiach approached the Chofetz Chaim with another incident.  A bocher who was dorming at the home of a widower where the facility and eating conditions were dire which caused the bocher to speak chutzpah to the widower. (Although the bocher was justified due to that specific circumstance.)

The Chofetz Chaim was upset about the bocher’s actions and said to send home the bocher away from the Yeshiva.

When the son-in-law questioned the Chofetz Chaim to compare the two instances, why one was sent home and not the other, the Chofetz Chaim explained his actions. “There’s a famous Mishna, “עז פנים לגיהנים ובושת פנים לגן עדן” – someone who is an עזית פנים doesn’t stand a chance to do teshuva, but someone who is a “בושת פנים” will do teshuvah!”