It all depends on how you define winning I suppose.
Or perhaps what I think is subtle is not subtle at all. I don't know!
On firmer ground, as a diversion try playing with triple letter words.... there's:
"weeest" [superlative of wee],
"Wiiitis" [a term for shoulder pain caused by excessive playing of the Nintendo video game Wii],
"Hostessship" is found in Shakespeare, Act 4, Scene 4, "Winter's Tale", and you could also have Goddessship, Postmistressship, Headmistressship, Governessship etc. in the same vein.
How about the quadruple letter word "Brrrr"?
All these words are found in dictionaries, somewhere!
If you are into such things, the reference is http://jeff560.tripod.com/words7.html
The full picture
Strewth uncropped. (see "Followers")