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I was reading definitions of unsparing

  1. Not merciful.

  2. Not frugal: unsparing generosity.

It seems that unsparing has two entirely opposite definitions.

I guess its meaning would be clear in context. I have a feeling that in the second definition, it has a negative connotation? Is this right?

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  • There is nothing negative about generosity. Your meaning (1), to be unsparing of (to not spare) someone is to judge them without tending towards kindness or favour. Whether this is negative depends on many things. To be unsparing of generosity, mercy, assistance, praise, gifts, etc is entirely positive.
    – Michael Harvey
    Commented Sep 27, 2018 at 21:59
  • Thanks, I guess it confuses me because when I use "spare money" I understood it as "extra" money".... and "sparing someone" has a sense of generosity.
    – Bryan Shih
    Commented Sep 28, 2018 at 7:06

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unsparing OED

Not niggardly; liberal, lavish; Showing no forbearance or mercy.

Unsparing is generally positive, but a negative connotation usage could be:

His evil towards his subjects was unsparing!

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