[citation needed] Pope worked for several years in Chicago’s budget department, serving also as Director of Demolition in the Building Department and Director of Conservation, before later joining Mayor Richard M. Daley’s staff as Daley's assistant.

[1] Pope was first elected in 1999 after defeating business owner Robert Wisz to succeed the retiring John Buchanan.

As an alderman, Pope served on a number of committees: Buildings; Economic & Capital Development; Energy, Environmental Protection and Public Utilities; Housing and Real Estate; and Police and Fire.

[1] In January 2008, Pope hired a former Streets and Sanitation worker, using a payroll account available to aldermen with no scrutiny, who was on a list of employees who should not be re-hired, as he had resigned after the city recommended firing him for allegations of sexually harassing a co-worker.

[3] In August 2015, mayor Rahm Emanuel appointed Pope as a deputy commissioner in the city's Department of Water Management.