Rose alludes to the name change of Chicago's famed Sears Tower to what we officially call the Willis Tower, however Willis Tower was not named for Benjamin Willis. In fact the Willis is named for Willis Group Holdings an insurance broker. And I'm guessing Mr. Rose more or less had a historical flashback.
Willis was appointed superintendent of the public school system in 1953, a couple of years before Daley the First assumed the throne, just around the time Chicago's African-American population -- or "Negroes" as we said then -- began to expand, largely because of a massive in-migration from the South.
Daley and his allies in the downtown business and financial community saw this as a big problem. Neighborhoods were changing rapidly on the South and West Sides and white folks began running from the city.
Many municipal instrumentalities were utilized to slow the expansion -- chief among them the creation of massive public housing projects within the existing "boundaries" of black Chicago, which set in concrete the housing pattern that would make Chicago the world's most segregated city outside of Africa.
Schools were the next most important focus. Nothing would change a neighborhood quicker than an influx of black kids into a white school. It became Willis' job to keep the school system segregated -- and he proved to be ingenious. He embarked on a vast school construction program -- gaining the nickname "Big Ben the Builder." The new schools were built primarily in white areas, far from existing color lines -- or well within the boundaries of what came to be known as the ghetto. (Mayor Daley famously opined, however, "There are no ghettoes in Chicago.")
Willis also juggled the boundaries of neighborhood schools to hem in the block-by-block growth of the black population that was forced by the real estate industry. Back then, in order to keep your license as a Realtor, you could not sell or rent to a Negro family outside of a two-block radius of the expanding ghetto.
Willis' quick fix in some areas was to fill the black schools' grounds with portable classrooms to prevent "overflow" into white schools. As protests against segregation grew in the early 1960s, the portable classrooms became known as "Willis Wagons." Eventually, there were 625 wagons in black schoolyards.
The black schools were underserved in many ways -- fewest experienced teachers, fewest ancillary health and social services and so forth. Separate really was unequal.
A very unfortunate time in our history of white flight and an unfortunate side effect is that Chicago is still segregated to this day! I can probably only count integrated neighborhoods on my hand. On top of this I shall refer you this video on a "skin disease". I won't explain I'll let the gentleman in this video do all the talking.