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It'd have been easiest to be the youngest at Azrael's era. Their core admins were all already above the age of 25, some with real jobs.
One thing on my mind, Why is Azrael remembered to these days over all the other admins that existed? Cause I remember NYN being much more influential on iClassic, not many remembers him nor his wife. Rest are like completely forgotten.
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Azrael, NYN, Ellybelly, Pimpsy and Xor were probably the most memorable for most players, I'm probably still forgetting about some others but these names popped up in my head first