In this particular case the winners get to pay for a rotator to pull the truck out of the Hole of Shame... And explain to DOT why were they on that road!
No, that's what quiters get to do. Winners will "Chuck Norris" chop down a couple of trees and build a bridge for the tandems. Me, I would roll through there no problems, sipping on tea.
The tractor is definitely on the left side ditch but I wonder if he was all the way to the left entering the corner....... Yes in the wrong lane........ trying to make the corner.....
At that should tell you everything you need to know about that road... It looks like the tandems dragged into the ditch,like the brakes locked up or something.