Yeravam’s David Dilemma
ומל יקוק אלקיך את-לבבך ואת-לבב זרעך לאהבה את-יקוק אלקיך בכל-לבבך ובכל-נפשך למען חייך
Hashem, your G-d, will circumcise your hearts and the hearts of your children, to love Hashem, your G-d, with all of your heart and all of your soul, so that you will live
A theme of this week’s parsha is that of repentance. Quite apropos for the time of year that we’re in. Hashem promises that He will circumcise our hearts. The idea being that just like the male organ has a physical barrier that must be removed, so too our heart has a metaphorical barrier that must be removed. The heart being the seat of emotions, Hashem tell us that what gets in the way of us serving Him properly is our uncircumcised hearts.
Our Sages tell us of an example of just how far an uncircumcised heart can lead us astray. Hashem, so to speak, grabbed hold of the garment of Yeravam ben Nevat, the wicked king of the Northern Kingdom of Israel. Hashem told him: “Repent! If you do, Me and you and the son of Yishai (King David) will stroll together in Gan Eden.” Yeravam asked: “Who will be at the head?” Hashem responded: “The son of Yishai.” Yeravam replied: “If that’s the case, then I’m not interested.”
There are many issues with his story. First of all, Hashem already said that “Me and you and the son of Yishai”, implying that Yeravam will be at the head. How then could Hashem switch it and say the son of Yishai will be first? Furthermore, this stroll in Gan Eden has to be referring to after Yeravam’s death, as one can’t be there while alive. That means if Yeravam doesn’t take Gan Eden, the only other option is Gehenom (Hell). How could he prefer that to having David be in the lead? Last question: Why did Hashem refer to David as “the son of Yishai”? Isn’t that disparaging?
We often attribute something that happens to the one that caused it to happen. For example, if Reuven caused Shimon to get killed, even if Reuven didn’t pull the trigger, we’d say that Reuven killed Shimon. It follows then that since Hashem causes everything, when a person is inspired to repentance, we can say that Hashem awakened the person to change.
One time there was an inspirational moment of improvement for Yeravam. He considered fixing his ways. The Sages referred to this as Hashem “grabbing on” to Yeravam, telling him to repent. However, the wicked are so deplorable that even when they’re inspired to repent, they don’t fully take advantage. In Yeravam’s mind, he was greater than David. That’s why he imagined in his head that Hashem was telling him that Hashem and he and David would stroll in Gan Eden; in that order. This is why he “heard” Hashem refer to David as the son of Yishai, as a way to disparage his rival in his mind.
However, Yeravam realized a problem. “Whose going to be the head?” If he repented sincerely, he would have to resume making the thrice yearly pilgrimage to Jerusalem, the home of his nemesis David and his descendants. “King David will be the head”. The kingship would return to David’s family. “If that’s the case”, thought Yeravam, “then I don’t want it”.
Our Sages tell us that jealousy can drive a person out of this world. We see with our own eyes how this came true with Yeravam. Only once a person allows their heart to be circumcised can they let go of their ego and properly serve Hashem.
 Based on Nachalas Yaakov to Deuteronomy 30:6, by the Nesivos HaMishpat, Rav Yaakov MiLisa
 Deuteronomy loc. cit.
 The verse even has an allusion to Elul (את לבבך ואת לבב), as brought by Mishnah Berurah 581:1. He presumably got this from the Abudraham Chapter 25 (Tefillas Rosh Hashanah), who quotes these allusions from the “Darshanim”. An earlier source for this allusion is Rav Chaim Paltiel to Deuteronomy loc. cit. Kitzur Shulchan Aruch 128:1 also brings this allusion, as well as other ones
 Sanhedrin 102a
 Rav Chaim Shmuelevitz, in Sichos Mussar § 82, gives a different, yet fascinating insight into this story. Yeravam was so obsessed with glory that once he heard that Hashem said, “Me and you and ben Yishai”, he just had to hear it again. It was too sweet to hear just once that he was ahead of ben Yishai. When Hashem perceived this, Yeravam was punished with David being first. Doesn’t explain though why Yeravam would have been at the head in the first place. Perhaps it was merely a test
 Cf. Kesubos 77b, where Yehoshua ben Levi went into Gan Eden alive. As well, Kallah Rabbasi 4:23 lists 7 individuals who went into Gan Eden alive, and Derech Eretz Zuta 1:18 lists 9. Both lists include Eliezer, the servant of Avraham. Yalkut Shimoni Chayei Sarah § 109 also mentions him, and adds that Yitzchak was in there as well. I assume the Nesivos means there’s no way for Yeravam to stroll in Gan Eden alive, considering how wicked he was
 See Psalms 4:3
 This reminds me of what I heard in the name of the Chazon Ish to explain the Beis Yosef’s encounters with the “Maggid”, an Angel who taught him Torah, as recorded in his Maggid Meisharim. See Ma’aseh Ish I p. 119 and VII p. 187
 The Nesivos seemingly didn’t address his issues with Gan Eden vs. Gehenom. I suppose his intent is that repentance will lead to Gan Eden, but Yeravam’s ego made him ignore the consequences of not repenting
 Avos 4:21