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In 2016, Kurt Summers, the Chicago City Treasurer, faced a decision with potential personal and political ramifications: whether or not to ask the city's Mayor to join a class action anti-trust suit against the city's creditors for actions they took during the Global Financial Crisis. Summers reflects on his time growing up in gang-controlled neighborhoods on the South Side of Chicago, and career experiences in both the public and private sector. These include stints at Harvard Business School, McKinsey, Goldman Sachs, the Chicago Olympics bid, and in local government. He tries to assess what he should do in this situation and what the best next steps would be in terms of his career. The case also discusses his work and leaderships styles, his personal life, including his relationship with his wife, and how he has adjusted to the new role of being a politician.