Personally, I think no one should even attempt to enter a raffle that isn't backed by a legitimate raffling site or isn't a free buy-in. The mentioning of raffling in a trade server is way too suspicious, along with spy crabbing. There are just too many untrustworthy people out there and people fall for them.
Mikey forgot to add:
http://steamcommunity.com/profiles/76561198078672522 This guy was the one who won the raffle, he looks like an alt (Considering they both have Christmas Swag in their name) His inventory is open to show he received the Level 100 TC (which is what was being raffled), but I suspect it's just an alt who "won".
If anyone would like to add, feel free.