Jacoby was visited by a SRPA team lead by Bo Richards and Nathan Hale, who came to arrest former Secretary of War Henry Walker, who they believed to be somewhere in the Freedom First cell within the city. However, Jacoby informed the Sentinels that Walker wasn't present in Chicago and had only heard that Walker and his wife were traveling to Montana before their disappearances. At first Jacoby was accused of lying to protect the Walkers, but Jacoby professed that if Henry Walker were trying to establish a treaty with the Chimera, he would have instantly killed him. Shortly after this, a Chimera raiding party entered the station. Throughout the conflict between the Chimera and the Sentinels and his forces, Jacoby steadfastly held his ground and boldly shot back at the raiders with dual pistols.
Jacoby was later radioed by Homer Munger stationed at a Freedom First camp in Montana, who caught Nathan Hale, and wanted to verify Hale's mission in finding Henry Walker. He did, allowing Hale to walk free.