Karen Freeman-Wilson is the Mayor of Gary, Indiana (population 78K), a city near Chicago where the violent crime rate is one of the highest in the nation. The Mayor has decided to go on Undercover Boss. In one segment, she is trained by police officer Emmons. The officer walks "Miss Sheila" through a training exercise. In an empty parking lot, Emmons and Miss Sheila (in the passenger seat) pulls over a speeding car. Emmons shows Miss Sheila how to safely approach the car. Emmons tells her she’s looking for additional movement in the car which could mean the driver is going to pull out a gun and shoot. That's when the mayor (Miss Sheila) asks the officer, "Anyone ever tried something with you?” Officer Emmons says "Yes, ma'am." The mayor looks out in the distance and says, "Oh my goodness.”
It's difficult to believe that the Mayor of Gary, Indiana (a Harvard Law grad btw) is surprised to learn that a police officer has had a gun pulled on her on the job. When it's Miss Sheila's turn to get behind the wheel and pull over a car, she gets out and approaches the car in a comical way. As the police officer comments, "it looks like you're going shopping." The producers of the show added a dopey song reminiscent of The Andy Griffith Show or Mayberry RFD to accompany the scene. Undercover Boss airs Wednesdays at 8pm and 9pm on CBS.
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— Undercover Boss (@undercover_cbs) December 20, 2016