Senator Geary's demands..
He obviously was dirty and was willing to take bribes and dirty money. Being a successful politician he should know how to play people. What then was the point about trying to ream Michael and to also insult him?
If he had asked for 50K for the gaming license he probably gets it. $250K? No way Michael pays him 5% off the top for all hotels. Just kill him and they do not have to pay. Not like there is a contract
Why was he so greedy and how could he misread Michael so badly? The point of the scene is how people underestimate Michael's intelligence and ruthlessness. Geary was just so over the top.