How much did Sam Gamgee spy on Frodo and Gandalf?

Question

In The Lord of the Rings, Book I, Chapter 5, “A Conspiracy Unmasked” Merry says that Sam collected a lot of information:

Here’s our collector of information! And he collected a lot, I can tell you, before he was finally caught. After which, I may say, he seemed to regard himself as on parole, and dried up.

Now, this puzzles me. The conspirators knew a lot. They knew about the Ring, and its provenance; they knew that the Enemy was seeking it, and why; they knew that Frodo was bound for Rivendell.

Most of that information was revealed to Frodo by Gandalf in one conversation (recorded in Chapter 2, “The Shadow of the Past”). And Sam was caught spying in the course of that conversation, so presumably did not pass on the information in that conversation to the conspirators. How, then, did the conspirators know as much as they did?

Answer 1

Sam must have reported the conversation in The Shadow of the Past

As you point out, much of the information you are asking comes only from Gandalf's conversation with Frodo in The Shadow of the Past, so any of it that Merry and Pippin are aware of must have been told to them by Sam.

The Shadow of the Past describes two conversations that Gandalf had with Frodo during that visit, one on the evening that he arrived and another the following morning. Gandalf stays a few weeks after that, but there are no more deep conversations in the text. We know that Gandalf mentions something about the ring in the conversation on the first night, but the important details came in the conversation the next morning which begins with Frodo saying:

‘Last night you began to tell me strange things about my ring, Gandalf,’ he said. ‘And then you stopped, because you said that such matters were best left until daylight. Don’t you think you had better finish now? You say the ring is dangerous, far more dangerous than I guess. In what way?’

_{The Lord of the Rings Book 1, Chapter 2: The Shadow of the Past}

Gandalf has been absent from the Shire for 9 years before this appearance. It is clear from the start of the morning's conversation that all Gandalf has revealed to Frodo up this point (and that only the previous night) is that there is something strange and troubling about his ring.

All of the information relevant to "the conspiracy" (that the Ring belongs to the Enemy who is searching for it, and that Frodo must leave the Shire and head for Rivendell) is learned by Frodo in the morning conversation. That conversation was overheard by Sam (before he was caught) and must have been reported to Merry and Pippin.

The only way to square this with Merry's statement that you quoted, is to assume that after he was caught, Sam considered himself "on parole" and so did no further spying. He must have convinced himself that it was okay to make a final report to Merry and Pippin of the information he had learned before he stopped spying.

I realise that may seem to be twisting the words a little, but I don't think it can be helped.

Answer 2

The available evidence indicates that Sam only spied during the events of the Shadow of the Past chapter, and no more.

First of all, we have a fairly precise timing of when the conspiracy was formed and when Sam started spying; from the conversation in A Conspiracy Unmasked:

'Well, as I was saying,' Merry proceeded, 'I kept my knowledge to myself, till this Spring when things got serious. Then we formed our conspiracy...'

So we know that the conspiracy was formed in Spring of that year.

Now, if we cross-check with the timing of Gandalf's visit, we see from Shadow of the Past:

It was early April and the sky was now clearing after heavy rain..... It was just at this time that Gandalf reappeared after his long absence.

Gandalf had in fact been absent from the Shire for nine years, so it must have been at this point that the conspiracy was formed and Sam began spying, with the reapparance of Gandalf as the trigger event: "when things got serious".

This gives a very short time-window for Sam to have been spying: from the evening of Gandalf's return (when Frodo and Gandalf stayed up late into the night talking) until the following day when he was caught.

We should note that during the course of the main conversation in Shadow of the Past there are a number of occasions where Sam's presence outside is referred to:

The sound of Sam Gamgee cutting the lawn came in from the garden..... Sam passed along the path outside whistling..... No sound of Sam's shears could now be heard.....

Although it's not explicitly stated it doesn't boggle the imagination to suppose that Sam was passing regular or semi-regular reports back during this time.