If you are interested in buying any of the event specific merchandise, there are RSP (random selection process) forms we fill out.
Since many of the pins are extremely limited this year, it's expected that they will sell out of almost everything. (Possibly all of the pins will sell out)
Here is a link to a good description of the RSPs how to...
http://www.pinpics.com/blog/pinpics-blog/raps-how-to
Winners means someone was lucky enough to have the item high enough in the RSP form and their name was drawn to receive that item.
For example, if 500 people want the LE 150 Super Jumbo. Only 150 people will be "winners", able to purchase the item at the price listed.