Two words: Lakeshore Drive.
Chicago has the same issue, but it has found ways to mitigate that issue. In addition, there is no 'moat' because it is connected to downtown through Cobo. Yes it is only one side, but the other side has the Ren Cen which has a good chunk of the City's employment and tourism.
I walk from my office to Hart Plaza often. If you sprint it you can make it across in one signal, but for most people it takes two. This is not an unusual amount of time to cross as many lanes as Jefferson has.
If you're real issue is the freeway, I don't know how that could realistically removed or reduced. Remember, this is still a critical link from the freeway system to an international border crossing and a major feeder into downtown's CBD. Burying the connector part won't work because there is already parking underneath. Even if we can double the transit trips it would not take enough cars out to completely remove the garage so Jefferson could be Wacker Drive.
Of course if the city does not have money for fire fighters, police officers, it will definitely be a long time before it will have the money for a major improvement to the transit system, a greening of Hart Plaza, or a partial burying of Jefferson Ave.
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