If all of his bets we're at least $100 it's sill easy for him to take the top 1 spot as long as he have enough bankroll and with autobet it would probably take several minutes since the bet speed is 1 per second. I wouldn't say wagering 14 bitcoins is a lot unless he went big and sniped yoloer on the last few minutes of the contest. There's a few ways to do it without spending more than the guaranteed prizes but with the screenshot it seems he wagered more than 10+btc in less than 4 hours which is quite fast..
I really don't get it. Windice has an house edge of 1%. If someone wagers 14 BTC to win 0.1 BTC (price for the first place) he statistically has lost 0.14 BTC during the contest. So wagering that many BTC has no sense in my opinion except "look guys how big my pockets are" ... or do I miss something?
Well, you are missing the point that he is dropping the house edge down. What would normally he get on a day there is no contest? 14 bitcoins wagered means 0.14 lost right? Well if he gets to win 0.1 of it back that means 14 btc is expected to lose 0.04 only and not 0.14 and that is why they play such huge amounts.
It is still not a guaranteed win but its at least a way to make some of it back, they could always get lucky and win some of it and that would mean break even or even profit for them. Sure they could lose a lot more as well but when you gamble 14 bitcoins there is a chance you hit some good rolls in a row and end up at the plus side. That's all they are trying to achieve here, yoloer even said he ended up with profiting on his second run for example.