As the Democratic National Convention approaches, Chicago reflects on its past experiences hosting such events. The 1968 convention remains a haunting memory, marred by violent clashes between police and protesters. However, the 1996 convention showcased a city that had learned from its mistakes. This year presents new challenges, with a more aggressive generation of activists fueling concerns. Mayor Brandon Johnson must navigate the delicate balance between freedom of speech and public safety, as the city hopes to avoid a repeat of past chaos.