Rashi cites the Sifri which translates the word rat, when, as implying hrat, fortunate and praised. This refers to a generation whose ruler directs himself to bring an atonement for a sin committed in error. How much more so when he repents of his deliberate sins! Why should the entire generation be credited for having a penitent leader? What role does the community play in its leader’s desire to publicly seek atonement for his transgressions?
Horav Moshe Shternbuch, Shlita, cites Rav Yisrael Salanter z.l. who explained this Chazal in the following manner. Some communal leaders do not follow in the prescribed Torah way. Their followers, however, fearful of reprisal, fail to point out the apparent errors of their leadership. They even go so far as to blandish them with a public display of respect. As a result of this pretentious relationship, the leaders begin actually to believe that they are righteous, noble, and deserving of their accolades. Consequently, when a leader comes forth to publicly decree his errors, it is indicative of his community’s aversion to his activities.
Horav Zalmen Sorotzkin z.l. expands on this Midrash. A leader’s errors are consistent with his personality and character. There are leaders who are imaginative and energetic, constantly seeking new ways to enhance their community’s lifestyle. Sometimes their enthusiasm exceeds their vision, and they undertake activities which should have been declined. This type of error is nonetheless understandable in contrast to the error of the leader who vacillates back and forth, hesitant to make any kind of decision. His inability to act expediently and judiciously results in grave consequences for his followers. This is Chazal’s message. Fortunate is the generation whose leader inadvertently sins in undertaking an activity, rather than one whose sin is the result of ineptitude, procrastination, or indetermination.