Well. Last game, he didn't throw a huge tantrum, for one. Which was weird on its own. For such a sore loser, he took that pretty easily--and Trickster loses when he doesn't get his mayhem.
So yeah, obviously he'd try for another game and likely when another Judge isn't going to pop in to ruin his fun. But that's exactly what happened. So Trickster plans his game and a Judge finds out and Messenger warns us? Or does Messenger know every game that's coming? If so, why has Messenger only warned us about two Trickster games? And not even the worst ones we've had. One was a repeat and one was... well. Who knows how things would've gone without the warnings.