Giuliani’s Comments Part of a Complicated History on Race

For those who first dialed into Rudolph W. Giuliani during his “America’s mayor” phase, right after the Sept. 11, 2001, terrorist attacks — when he wowed the world with his civic leadership, soaring oratory and unifying largess — the former New York mayor’s racially charged comments about President Obama might seem puzzling.

But Mr. Giuliani’s road to and through City Hall was punctuated with racial controversy.

From his 1993 campaign challenging David N. Dinkins, the city’s first African-American mayor, during which Mr. Giuliani stood with rowdy protesting police officers —...