Of Gandalf and Frodo’s dilemma
The end of chapter 2 is a long dialogue between Gandalf and Frodo. The first tells the story of the ring, and all its ramifications; the second, while listening to it, becomes more and more reluctant to set off on his journey. The peak moment is when they test the ring and throw it in the fire, but there is a quieter bit, a few pages after, that is easy to skip over (it’s only a paragraph long), but that should speak volume to us.
While learning about Gollum, and how he was initially a hobbit, Frodo is very distressed. To the point that he says: “What a pity that Bilbo did not stab that vile creature, when he had a chance!’
To which Gandalf absolutely disagrees. “Pity? It was Pity that stayed his hand. Pity, and Mercy: not to strike without need. And he has been well rewarded, Frodo. Be sure that he took so little hurt from the evil, and escaped in the end, because he began his ownership of the Ring so. With Pity.”
So did Bilbo acquire the ring. There is a very important theme here, about the adequation of the receiver and the thing he receives that we will develop in a later essay. For now, let’s focus on the personality of Gollum.
Frodo insists: he doesn’t feel any pity for Gollum. Worse, he accuses Gandalf and the elves of failing to bring justice and thus being complicit with Gollum: “I can’t understand you. Do you mean to say that you, and the Elves, have let him live on after all those horrible deeds? Now at any rate he is as bad as an Orc, and just an enemy. He deserves death.”
Which, if we follow all the news that Gandalf just gave, makes sense: Gollum sold his own people to the enemy. Now Sauron knows about the Shire and the Bagginses.
But Gandalf completely disagrees. Maybe because “wizards are quick to anger”, or maybe because he doesn’t like to be second guessed, of all people, by a hobbit.
“Deserves it! I daresay he does. Many that live deserve death. And some that die deserve life. Can you give it to them? Then do not be too eager to deal out death in judgement. For even the very wise cannot see all ends. I have not much hope that Gollum can be cured before he dies, but there is a chance of it. And he is bound up with the fate of the Ring. My heart tells me that he has some part to play yet, for good or ill, before the end; and when that comes, the pity of Bilbo may rule the fate of many – yours not least.”
The opening of his argument is interesting: if you bring justice by killing those who deserve it, are you capable of bringing justice to those who are killed unjustly by bringing them back to life?
To the literate Jewish reader, this argument evokes a famous midrash, situated towards the end of the life of Moshe Rabbenu (in Deuteronomy, parashah Vehathanan). The tradition tells us that Moshe argued with God for his life. God informed him that he would not enter the land of Israel, and Moshe petitioned him with no less than 515 different prayers.
In one of them, God tells Moshe Rabbenu that he killed the Egyptian man. To which Moshe says: “And you, God, you killed all of the Egyptian first-born, the innocent along with the guilty, and yet you would kill me on account of the one Egyptian whom I killed in the act of rescuing my fellow?”
“The Holy One, Blessed be God, said to him: Do you compare yourself with me?! I can bring death, and life as well, even to those who are already dead! Can you bring the dead back to life?!” (Midrash Petirat Moshe)
Gandalf apparently knew this midrash well (!), and uses the same argument. Power of death only for those with the power of life.
Following the same logic, Gandalf insists that Gollum should not be killed. “do not be too eager to deal out death in judgement. For even the very wise cannot see all ends.”
And he explains that no one knows what Gollum will do: maybe he will choose good over evil, and prove, in the end, decisive (I don’t think it will spoil anyone at this point to say that Gandalf is correct, and that Gollum will prove to be decisive).
In this short argument, Gandalf identifies a very interesting pattern. There are some rare people in troubled times, whose destiny takes turns that completely defy common logic. Gandalf acknowledges this possibility, and hence his reluctance to act.
For us, who live during similar times, we can point to a few examples of this pattern.
The most striking one, at the moment (I write this mid-July 2025 of the common calendar) is the destiny of the current president of Syria: al-Sharaa.
Here’s a man who started in 2012 as an Islamist, affiliated with the Islamic State in the Levant (called ISIS in English, Daesh following its Arabic acronym). Thirteen years later, he took over Syria in a few weeks, and completely changed his path, the path of his followers and of his country. The images were striking: every week, at every meeting with a western leader, he would appear with a better trimmed beard and a nicer western suit. For a while, people were puzzled: was it just an act? Both the US and Israel seemed ready to give this a chance, and were talking about extending the Abraham Accords to Syria, which would secure an even bigger peace for the Middle East. All this until July 16, 2025, when Syrian troops massacred Druzes in the South-East of the country, before being stopped by the Israeli army. A cease-fire was reached in less than 24 hours, and al-Sharaa now insists that Druzes will be protected, and their tormentors prosecuted. Maybe he too “has some part to play yet, for good or ill”.
There are other examples of this type of person (one can think for exemple of Abu Shabab). Not all of them carry the day. An infamous example was Sinwar, a man who was imprisoned in Israel for 22 years for the abduction and killing of six people (two Israeli soldiers and four Palestinians he considered to be traitors). In 2004, after falling while praying, doctors discovered he had a brain tumor, and treated him at the Be’er Sheva hospital. He healed, and was released in 2011. He went on to become the main architect and leader of October 7 and the war that followed, until he was killed in October 2024.
These two examples show the crux of the debate between Gandalf and Frodo. While facing an important enemy who probably deserves to die, who is the person: a future Jolani or a future Sinwar? Impossible to know. The only thing Gandalf has is “his heart”. Which, to circle back to the biblical times (in the Middle East, they are never far) is to say that all he has is “prophecy”. We don’t have this much; and we are left with the alternative. What path to follow? The path of Frodo or the path of Gandalf? This is a dilemma we have to solve again and again.