I have just finished reading this sentence in Tolkien’s Lord of the Rings:
In fact, I’ve never taken anything on a journey that I’d have been less sorry to lose on the way.
Samwise says that of Gollum.
I know from broader context that Sam is implying he’d be happy to have lost Gollum on the way. But I’m struggling to understand the double negatives. How do the double negatives compound to result in the implication? Is it better phrased as, never have I taken anything on a journey which I’d be sorry to lose? But how does ‘less sorry’ make sense here?
I hope you can see or understand my difficulty here, I’m having trouble expressing it.