It seems like the Chicago Teachers Union has been able to get at least a good portion of what they want by striking in the past. Having kids out of school for too long puts them behind and that is powerful leverage.
I am not sure that will be the case going forward. It looks like Chicago Public Schools is tapped out. While I am sure there is plenty of blame to go around for that circumstance, the teachers may not be happy with how the next strike turns out. Apparently their current planned action is a one-day walkout. But that would not be happening if they did not have an axe to grind. It has the air of being an opening salvo.
It is getting to the point where Chicago Public Schools is having trouble going to the bond markets now. last month they managed to sell $725 million worth of bonds, but only after reducing the offering size and paying a very high interest rate. Without that pressure release valve it seems like the options probably get pretty black and white.
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References:
http://abc7chicago.com/education/ctu-votes-to-authorize-walkout-on-april-1/1259705/