something I don't get

I can only speculate but it seems he had ears and eyes everywhere. According to what I have read on the script, he had planned this con for a long time and paid off the tenth fighter ahead of time just in case. But there were clues that helped confirm his suspiscions. When they were drafting the terms of the bet and they stated that Olivare county (prison's location) is also Diggstown. Couple that with the warden's promise to "See him again" and the obvious reputation of Menosa as one of the deadliest of fighters, it was likely educated speculation that he had planned for.




"Mankind cannot solve the world's problems. Mankind is the problem."

I haven't seen it in a long time, but my take based on my memory is that Caine felt that Roy could beat any eligible fight except for Torres so he bribed Torres. Gillon however surprises Caine by bringing in Hagan as a ringer. Caine was not prepared for this, but Roy manages to beat Hagan anyway.

Gillon had two ringers. One Caine new was a potential fighter and bribed, and one who surprises Caine. Roy take out one by fighting that fight of his life, and the other is in Caine's pocket.

You have to remember that they weren't even expecting a 10th fight. So the surprise ringer was Hammerhead.

Caine had no idea Torres would be fighting, everybody just assumes he knew this and the dive was part of a long con. In reality its more likely Torres just owed Caine a favor from their time in prison, and Caine fortuitously used that to get an easy win and show Gillon his ass at the same time.