They really come across as a bunch of CoWards, and they certainly are a very manipulative group... in both, they very well continue the tradition of their de facto founders, the Shadowmen - who used a girl/young woman to fight their fight for them.
Strange thing about the CoW, to me, is the contrast between the members themselves being utter wusses and nerds, who often are as by-the-book as it gets (like S1 Giles, Wes on Buffy, or most of the cameo Watchers we see), while they command henchmen portrayed as ruthless fighter not caring about what laws get broken in their mission (like the team sent after Faith/Buffy in S4). In that regard, they closely mirror The Initiative - or more precisely, the military officials commanding the Initiative from up high... behind-the-desk generals sending combat troops into the field.
The parallel to "military facelessness" is especially striking if you consider that our main cast Watchers only gain any memorable personality to speak of when they've gone rogue in some way (Wesley on Angel; and Giles, who's been more and more shunned even before he got fired, starting when we learn of his Ripper past - before that, he definitely seemed like an older version of S3 Wesley. Just rewatch some training scenes with Giles and Buffy in S1 and early S2 and ask yourself how that wussy librarian could ever have been Ripper, especially when you compare it to "letting the Ripper out" in his scenes with Ethan!).
Even "cameo rogues" like Gwen Post or the ex-Watcher (forgot his name) working for W&H in Angel's S5 seem like carbon copies of the Watcher cliché - bookish nerd, stickler for rules, loser in a physical fight, but manipulative to reach their end. In the end, the tweed suit seems just another kind of uniform. 😀
