He wasn't semi-solvent.
Both were broke, and a long line of Jason's creditors have come forward in that 2+2 thread.
Jason was doing more than "cutting corners". He was freerolling, and clearly had zero ability to pay Chris, had he won.
Furthermore, Jason did an additional scummy thing by creating a fictitious character booking the bets, thus allowing himself to wriggle off the hook if he lost (blaming the unknown bookie).
Chris was also freerolling.
The whole bet should be void, since it was a double freeroll, with the added complication of a fictitious third party supposedly booking Jason's side of the action.
Had Chris won the bet, though, I would have been on Jason's side, especially after seeing these texts.
Basically, I'm on the side of whomever is being asked to pay in this double-scam. No money should change hands in this clusterfuck.