Indeed, if Rahm becomes mayor, he would choose both the Chicago Gaming Commission and the management of the casino.
No potential conflict of interest there.
I think there is a broad consensus that this is an opportunity for continuous employment in the U.S. attorney's office.
Mayor Daley always was ambivalent on gambling in Chicago. He derided the original riverboat gambling in Illinois as "Putt-Putt boats" beneath the dignity of Chicago. Given the huge success of the riverboats, most view this as one of the bigger mistakes of this tenure. There was wide spread speculation that when Daley ripped up Meigs Field part of the motivation was to produce a site for a land based casino. This has not occurred but still is an open question. Rahm has not expressed a view on gambling to my knowledge but has been supportive of Daley's resistance to higher tax rates. Illinois is in a massive budget hole, multiple billions of dollars, and while the governor has called for a 50% increase in the income tax, the legislature does not appear to have the stomach for it.
I do not think that the Chicago electorate has any strong feelings one way or the other on gambling