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  1. Your judgement is as clouded as John's was when he did that stupid thing.

  2. Your judgement is as clouded as how clouded John's judgement was when he did that stupid thing.

  • Do both these sentences mean the same thing?
  • Are they grammatically correct?
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Yes, but you can omit the "how clouded" in the second sentence as it's repetitive and unnecessary. When reading the first sentence I completely understand the meaning just as much as the second sentence. Therefore the extra "how clouded" is unnecessary and can be deleted.

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Both of your sentences mean the same thing, however, your expansion of the original simile in your example

Your judgement is as clouded as how clouded John's judgement was when he did that stupid thing.

is understandable but awkward and verbose.

In school, it is taught that

Your judgement is as clouded as John's

can be expanded (for meaning) to

Your judgement is as clouded as John's judgement is clouded

Your second sentence could be reformulated as

Your judgement is as clouded as John's judgement was clouded when he did that stupid thing.
Your judgement is as clouded as John's when he did that stupid thing.

In the second sentence (above) "was" is redundant since past tense is implied by "did".

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