The Mahiril says that Elul is a time to remove thorns from the ground so seeds can be planted. Many do teshuvah on Yom Kippur but repeat their sins afterwards because they didn’t uproot the shoresh of the sins. (You need to remove the thorns to do that.)
Around 40 years ago, Rav Elya Ber Wachtfogel was at a hotel in Eretz Yisroel that was owned by the Agudah. Since they had given rooms half price to yeshivaleit, the hotel had become a meeting place for Roshei Yeshiva, Rabbanim, and yeshiva talmidim.
Since it was an Agudah hotel, they gave out free copies of Hamodia, the Agudah’s newspaper. One man, a Polish Jew, didn’t pick it up off the table. He didn’t seem like a kanoi so the Rav asked him about this.
The man said he was raised in the city of Lodz and studied at the local yeshiva. He spent his days learning but was a curious young man and would read many of the non-frum newspapers, enjoying in particular a “well-written” column by an anti-religious communist. He started to lose interest in learning and eventually stopped putting on tefillin. By the time the Nazis arrived in Lodz, he was in his words a “goy gamur.”
Determined to join the Soviet paradise, he slipped across the border. Rather than find a Gan Eden as he hoped, he found a gehennom. The Russian communists, led by Stalin, despised Jews and tortured and killed the Jewish communists. Only this one young man and a friend survived from the group that had crossed the border.
After the war, he came to Eretz Yisroel where he did teshuvah and became observant again. He vowed never again to touch a newspaper.
This is an example of uprooting the sin.
We see this dynamic again in the Gemara where a bas kol offers Yerovam ben Nevat, the wicked king of the northern kingdom of Israel, the chance to do teshuvah and walk with Hashem, Dovid, and Yerovam in Gan Eden. Yerovam asked, who will be first? When told Dovid would be first, he rejected the offer.
How could he reject such an offer? A daf earlier we had learned that Yerovam merited to be king because he rebuked Shlomo HaMelech for marrying the daughter of Pharaoh. When the time for regel arrived, he reasoned that he would have to stand in the Beis HaMikdash while Shlomo’s son Rechaivm would sit, as only one person could sit on the throne. This would make him look like an eved. Rather than have that happen, he prevented people from traveling to Yerushalayim and set up idols to worship instead.
The shoresh of his sins was the desire to be b’rosh, in command. The Gemara is telling us he could do teshuva for all his sins, but as long as the shoresh remained, the teshuva would not last.
Says the Rosh Yeshiva, we must all examine ourselves to locate the shorashim that need to be uprooted.
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