Esther 1:19, Question 5. What does the phrase “better than her” indicate in relation to Vashti?

Certainly, one would expect the next queen to learn from the example of her predecessor and be very careful to always listen to the king. In pointing out that this phrase is a definite allusion to Esther, the Midrash (Esther Rabbah 4:9) states that Scripture uses the very same phrase of “better than you” (Shmuel 1 15:28, albeit in the masculine form) in both the removal of kingship from Esther’s ancestor, Saul, as well as the beginning of Esther’s ascension to the throne here. The Dubno Maggid explains that the Midrash is demonstrating how H-Shem allows a characteristic that had a seemingly negative aspect in one instant to have the exact polar opposite effect elsewhere. This was the particular aspect of H-Shem’s hashgacha (mida kineged mida) that Yisro praised in saying “[the Egyptians’] own plots turned against them” (Shemos 18:11, see Rashi there). Rav Chaim Volozhin in Nefesh HaChaim (1:7) elaborates on the mechanics of this theme.