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I fully understand the ickiness, and I say that as a fan. Christopher Ward are unique in that their logos keep getting worse and worse, and I think that's made it a bit of a 'thing' that it wouldn't otherwise be.
I bought a Trident from the second generation (with the old ChrWard logo) and I always wanted one from the previous generation because I hated the logo so much. (It looks like the word COWARD from a distance, and once you see it you can't unsee it).
Then the third generation logo came along and I started counting myself lucky that I got the second generation one.
It's a bit like the problems Helson had at the start with waterproof-ness. It could've been brand-ending but they sorted it out within 2nd gen and now no-one really talks about it anymore. Christopher Ward could've done the same quite easily with a decent logo.
I'm with you on Oris too. Its more ignorable than CW though.