When you say "he doesn't fail to disappoint", to me it has a negative meaning as in he always disappoints. But I've heard some people using it as a compliment and in a positive way. So, am I wrong about the meaning or it's the other way around?
For example, Christina said on Voice:
My glam team doesn't fail to disappoint and they took the Monday blues
and turned it into a stunning look any girl would love.
Best Answer
"Never fails to disappoint" in the OP's quote seems to be a good example of what the linguists on Language Log call a misnegation, whereby the utterance means the opposite of what was intended. Here is a sample of the misnegations they analyse:
There are many more of these at: http://languagelog.ldc.upenn.edu/nll/index.php?s=misnegation