Often as a rabbi, the easiest thing you can do is tell someone what they want to hear. It alleviates their pain (if only temporarily), makes you look better, and to some degree, allows them to take leave of you in a better mood than when they arrived. Yet, while that's almost always the easiest path, it's not necessarily the correct one.
A conversation my mother last week turned to the topic of the passing of Rav Chaim Pinchas Scheinberg last week. My mother explained that while she's not one who often visits gedolim in search of brachot, she once accompanied my brother to go visit Rav Scheinberg and to receive a brachah from him.
When they arrived at his apartment and met the rav, my mother asked for a brachah that she find a shidduch. (She's been a widow for a long time now, and has long wanted to remarry.) Rav Scheinberg looked at my mother who had come with her son and grandsons and said, "I give you a brachah that you have nachas from your children."
My mother got the picture. She didn't press. Rav Scheinberg didn't want to tell her what she wanted to hear, but offered her a meaningful blessing nonetheless. Why didn't he bless her that she should find a shidduch? Either:
1. He had a level of ruach hakodesh and didn't see remarriage in her future
2. Forget ruach hakodesh. Finding a second husband is quite rare and he didn't want to raise my mother's hopes on something that would be a long shot.
Either way, while it must have been hard for my mother to hear the blessing at the time, she now views his brachah as a symbol of kindness. Rav Scheinberg could have easily given her the blessing that she wanted. And then, when his grandson solicited her for a donation when she came back down the steps (as he did), she would probably have given him a great deal more money.
But he didn't want to tell her what she wanted to hear. He told her what he thought was best for her. That's real greatness.
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