Our Gemara on Amud Beis tells us the evil Turyanus who taunted Papus and Lulyanus, saying “Why doesn’t your God save you like he saved Chananya, Mishael and Azariah in the time of Nebuchadnezzer?” They replied, Chananya, Mishael and Azariah were fully righteous and furthermore, Nebuchadnezzer was a legitimate king, worthy of witnessing such a miracle.

Despite being a cruel despot, there is no question that Nebuchadnezzar was a man of substance. He was able to praise God effusively as well as take Daniel’s advice to give voluminous charity in order to stave off an evil fate that was prophesied (Daniel 4:24, 44)

This is an interesting archetype in rabbinic literature which I call the Worthy Rasha. He makes appearances in different forms, as I shall explain, and offers a lesson.

For example, the Gemara tells us the following story about the genocidal King Menashe (Kings II:21:16 and Sanhedrin 102b):

In one of his shiurim Rav Ashi referred to King Menashe as a “colleague”, and Menashe angrily came to him in a dream to scold him. “You don’t even know the halakha of where to cut the bread when reciting the blessing and you dare consider me to be your equal???”

Rav Ashi eventually learns the halakha from Menashe in exchange for pledging to say the teaching over in his name. Rav Ashi henceforth referred to Menashe, Achav and Yeravam as “Our teachers”.

Rav Ashi asked Menashe, “If you were so great in Torah, why did you serve idols?” Menashe answered, “Had you been living at that time, you would have taken and lifted the hem of your cloak and run after me!”

The Gemara (102a) there also discusses a fascinating vignette about the wicked Yeravam:

⁦Rabbi Abba says: It is after the Holy One, Blessed be He, grabbed Yeravam by his garment, said to him: Repent, and you and I and the son of Yishai will stroll together in the Garden of Eden. Yeravam said to Him: Who will walk in the lead? God said to Yeravam: The son of Yishai will walk in the lead. Yeravam said: If so, I do not wish to repent.

And similarly, according to the Maharsha’s interpretation of 102b, Achav was at times deeply connected to God when he was in trouble and prayed sincerely. Though once out of danger, he attributed his success to foreign gods.

The rabbis understood greatness as different from goodness. Persons who achieved a status of leadership either often have the qualities or grow into the quality of greatness. The Kings described were tyrannical and immoral, yet they also had the ability to recognize God and merited to witness wonders.  

The story about Yeravam is most striking.  He is offered Eternal Life in the Garden of Eden but cannot settle to be second place with King David.  The need for success and competency is a basic human drive, but taken to the extreme can cause downfall instead of achievement.    Often people whom we experience as deficient in character and morals, are deep down, perfectionists such as Yeravam.  They cannot allow themselves to try and work toward their aspirations because they cannot live with any possible failure. They would rather go down in a blaze of glory and be utterly successful at evil than to be moderately successful at being good.