Rashi comments that Hashem increased Yosef’s prison sentence by an extra two years. This was because he had placed his trust in the Sar Ha’Mashkim, by asking him twice to remember him before Pharaoh. What would have happened if Yosef had asked him only once? Would he have been punished with only a single year?
This question was posed by Horav Shimon Shkop, z.l., to a group of his students during a session devoted to reproving them for behavior unbecoming a ben Torah. The economic conditions in the yeshivah of Grodno, in which Horav Shkop was Rosh Ha’Yeshivah left much to be desired. In protest, a group of students who desired to express their discontent with the situation, left for a day to study in a different Bais Ha’Midrash. At the end of that day the Rosh Ha’Yeshivah sent a message to the young men that they were “expected” to return the next morning for shiur. Horav Shkop walked into the room and began to reprove their actions of the previous day. He prefaced his words with the question, “Would Yosef have been punished with one year had he only asked the Sar Ha’Mashkim once?”
The Rosh Ha’Yeshivah responded, “No, he would not have been punished at all. Everyone is permitted to make an effort to improve his lot. By asking the chief butler to remember him, Yosef did not demonstrate a lack of faith. When he asked him a second time to remember him, however, he indicated that his previous request was also inappropriate. One request is permissible; it does not suggest impropriety. The second request, however, is inappropriate and indicates distance from Torah perspective. Yosef’s second petition cast a cloud upon his first request and catalyzed his punishment.
“Likewise, my students,” said Horav Shkop, “the first time you left the yeshivah, you made a statement which does not necessarily demonstrate inappropriate behavior on your part. If you entertain the thought of going a second time, be aware that you will be crossing the boundary of rectitude. Immediately return to the Bais Ha’Midrash and forget this nonsense!”