2 fixed one typo
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BotheBoth 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".

Bothe 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".

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".

1
source | link

Bothe 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".