Honestly, I’ve been around for so long that there isn’t one particular loss that stings the most. However, I can talk about the first ever player I had on here, which was Ben Wong. A hall of famer, multiple individual awards, a Canadian gold medal, but no Challenge Cup. That one stung, but I don’t think I would’ve been as hungry with my next 2 players to win a Challenge Cup. Ben Wong, was a long time Toronto North Star, spending majority of his career there. This was in an era most draft picks started playing right away, so while Ben’s career was short, all of it was spent in the SHL. In my rookie season with WKP before being traded to Toronto, we lost in the finals to the Calgary Dragons (who by coincidence is the team I finally won my first Cup with, but with a future player), then Ben Wong wasn’t able to make it past the first round in Toronto (I’m not even kidding) and after trying to stack 3 teams, 2 on Manhattan with the Scherbluks and JNH, while the other on the Wolfpack with Ace’s crew at the time, but all were unfortunate failures. Never winning a cup with Ben sucked and honestly still sucks.