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It's not who you con. It's how you do it.
When 5 allied generals are captured in Italy in WWII, it is a propaganda nightmare for the allies. The generals are all 1 star and refuse to take orders from each other in order to plan an escape. Harry Frigg is a private who has escaped from the guard house dozens of times. He is promoted to Major General and ordered to get the generals out once he is captured. Harry is willing to escape, but then he meets the countess...
Jack Smight

Pvt. Harry Frigg

Countess Francesca De Montefiore

Gen. Newton Armstrong

Gen. Roscoe Pennypacker

Gen. Francis Mayhew

Gen. Adrian Cox-Roberts

Col. Enrico Ferrucci

Gen. Andre Rochambeau

Maj. von Steignitz

Gen. Homer Prentiss

Lt. Rossano

Sgt. Pozzallo