This was a tough poll for me because there are so many things to factor in. Many of the characters that existed in the DS universe had a problem to contend with, whether it was self inflicted or caused by someone else. So my votes went to:
Vicki Winters: Because damn, if she didn't get stupid as time went on. It seems that her loss of intelligence could've stemmed from the various things she had to go through at Collinwood, such as that threateningly insane charge of hers, the persistant refusal of her questions about the reasons for which she was hired and about her lineage. And, oh yea, perhaps the biggest thing that ever happened to her intelligence was the arrival of that very OLD man who somehow seemed to captivate everyone. Plus, ya know, she went through all that drama with going back in time, being tried and hanged as a witch, then losing her love, finding him, and finally, being pushed off a cliff.
Maggie Evans: Because, as everyone knows, she was once a tough-talking sass who told it like it was, and then some. Her demise seemed to come as soon as the very OLD man mentioned earlier came into town, and after Vicki disappeared to Barnabas-knows-where, Maggie was offered the position which would nail the final hinge on her coffin--governess at Collinwood. Where, she would subsequently be frightened by Mr. Juggins, become the always tread upon lady (since the spot was vacated by Vicki) and oh yea, her Pop's was killed by the ex-scorned lover of the man who was interested in her.
Angelique: Because she caused so much shit in her quest for a certain very OLD man, yet recieved so much shit in her quest for a certain very OLD man. 'Nuff said.
Jason McGuire: An unlikely choice, yes, but a reasonable one. For months he tormented Liz with the thought of her husband, Paul Stoddard, being dead, when, in fact, he wasn't. Jason extorted Liz and made various advances at her, attempting to get her to marry him, all so that he could get her money and the Collins estate for himself. But, when a certain very OLD man arrived, Jason was quickly snuffed out. And, let's face it, he didn't achieve his ultimate goal. And as many of us know, not achieveing a goal which you have been working so hard towards for so long, can be quite depressing and make one feel like a loser. Plus, to be so twisted, sick, demented, wrong, and abusive, you have to know that his life previous to Collinwood was a big shit hole.