Mayor Rahm Emanuel will trade barbs with David Letterman Monday when he appears on the "Late Show."
Emanuel is expected to discuss the Discovery Channel documentary "The Presidents' Gatekeepers," which features all 20 living White House Chiefs of Staff.
Emanuel served as President Obama's Chief of Staff for two years before resigning to ramp up his campaign for Chicago mayor.
Illinois gubernatorial candidate Bill Daley, who also had a stint as Obama's Chief of Staff, also appears in the documentary, which airs on Sept. 11.
It'll be Rahm's first appearance on the CBS show, but if the issue of Chicago violence comes up, there's a chance things could get prickly.
NBC 5 has reached out to the mayor's press team to ask how he might react to those questions on the talk show, but no response has been received.
Requests for reaction to Stephen Colbert's comments about Chicago's gun violence this week have also been met with silence.
While talking about plans for a military strike against Syria, Colbert said "if America cared about shooting people, we'd be invading Chicago."