You could turn the question around on Montana and ask if it makes sense to risk his reputation and image, which has led to lucrative appearance fees, endorsements business opportunities, etc. over a single event. Pretty foolish on Montana's part if you aske me.
If I was his agent, I would have told him he was risking mulitples of that $100,000 sum by looking like such a clown. Then again, most agents can't see the forest through the trees.