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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.

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Breaking it down in steps:

In fact, I’ve never taken anything on a journey that I’d have been less sorry to lose on the way.

Remove non-essential bits

I’ve never taken anything on a journey that I’d have been less sorry to lose

Add in the implicit object of comparison

I’ve never taken anything on a journey that I’d have been less sorry to lose than Gollum

"less sorry" = "happier"

I’ve never taken anything on a journey that I’d have been happier to lose than Gollum

"There is nothing more X than Y" = "Y is the most X"

Of all the things I've ever taken on a journey, I'm happiest about losing Gollum.

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  • Thanks so much for the breakdown, it helps greatly for this and future double negatives I will run across.
    – MapleCarer
    Oct 12, 2022 at 10:56
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    No double negatives show in the original. Though deliberately complicated for subtle emphasis, it places never and less in separate clauses. Oct 12, 2022 at 13:40

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