When Leslie finds out Jerry is retiring, she struggles with the proper way to commemorate the occasion. Chris and Ann prepare to have a baby together, while Tom worries he will become the office punching bag once Jerry leaves.

Leslie celebrates her first year as a city councilor. A surprise discovery leads Andy to call the only man he knows who can help with the investigation: retired Special Agent Burt Macklin. Meanwhile, April gets some life-changing news, and Tom debates a big business opportunity.