Team O'Neil is giving it away on facebook. Give me a second and I'll post the answer to the trivia question. I have a similar paperweight so I'm willing to do the research and let someone else get the swag this time.
Update: 12 wins
2011: Dillon Van Way @ Sno*Drift, Chris Duplessis @ New England Forest
2012: Chris Duplessis @ Sno*Drift, 100 Acre Wood, Susquehannock Trail, & Olympus
2013: Brendan Reeves @ Oregon Trail, Susquehannock Trail, New England Forest, Ojibwe, & Lake Superior
2014: Andrew Comrie-Picard @ 100 Acre Wood