Or cutting messages into other people's skin! Nah Umbridge was a Ministry of Magic lackey and sucked up to Cornelius Fudge big time (perhaps literally). But Winn is definitely more strangle-able (if that's a word), simply because she pretends to be good, but she is totally rotten inside.
Whereas Umbridge was always a hag and was never two-faced. Winn however was a far more complex character, and with virtually every line of dialogue she uttered, I feel like throttling her to death! She is so... patronising, condescending, belittling, devious... (but that's why she is such an amazing character)