Defining "Cunning" in a Chicago Context: Need the Passage

I cannot define "cunning" in relation to Chicago without the specific passage you're referencing. The word's meaning shifts dramatically based on context:

Possible Interpretations

• Positive/Admiring: "Chicago's cunning urban planning" — clever, resourceful, innovative solutions (reversing the river, deep tunnel, lakefront preservation)
• Negative/Critical: "Cunning machine politics" — manipulative, corrupt, self-dealing (Daley machine, ward heelers, patronage)
• Neutral/Descriptive: "Cunning adaptation" — shrewd survival strategies (neighborhood resilience, informal economies, cultural code-switching)
• Literary/Character: A "cunning Chicagoan" in fiction — street-smart, calculating, perhaps morally ambiguous

Chicago-Specific Connotations

Chicago literature (Dreiser, Wright, Algren, Bellow, Cisneros) often portrays "cunning" as survival intelligence in a harsh urban environment—not inherently good or bad, but necessary.

Please provide the passage for a precise analysis. The author's tone, the subject (person, institution, policy, neighborhood), and surrounding sentences determine whether "cunning" means clever innovation, corrupt manipulation, street smarts, or something else entirely.