Okay - CLEARLY Flug has been with Black Hat for a VERY long time. Assuming Villainous takes place in present time, we can assume that Dr Flug is immune to aging just as Black Hat is. In the “Anti-Gravity Device” episode, there’s a picture of Al Capone kissing Black Hat’s hand with Dr Flug in the background. While it IS possible Flug could have been alive at that point, that would make him old now, considering Al Capone was around early 1900s, that would put Flug at roughly around 100 years old. Dr Flug doesn’t look to be anywhere near his 90s and seems quite able bodied. Thus, my case, Dr Flug doesn’t age and must have been with Black Hat for much longer than it would seem.