There is another meaning of "looked him off" in sports, which is related to your second link but somewhat different because it is cooperative:
"looked him off" = "signaled to him (with my eyes / without words) that he should not make an attempt or play"
In context:
I was about to run toward the goal so Mark could pass the ball to me, but he looked me off. So instead I fell back and let Jenny cut toward the goal. Mark passed to Jenny and she scored!
Without seeing the movie it's hard to say for sure, but this meaning could fit your excerpt. In that case, the sentence would mean
"The first time I met Reuben, I was about to play a game. Of course, I didn't know it, but the game was rigged, and I was about to be cheated! Fortunately Reuben silently signaled to me that the game was rigged, so I decided not to play, and in this way I avoided being cheated."
This would explain why he has been friends with Reuben since then.