Democratic gubernatorial candidate David Jolly visited Dara in the Speakeasy this week as he travels throughout the state in the run-up to next year's election! Join Deeper Dive to hear David reveal how Charlie Kirk's assassination prompted him to assess whether he wanted to remain in the race for governor. David, a former Republican congressman who spent the past eight years as a political consultant for MSNBC, shares his concerns about GOP leaders' crackdown on speech. Can a Democrat win statewide in Florida next year? David tells Dara why he believes voters are looking for a change in 2026. The pair also discuss the candidate's plans to address the state's property-insurance crisis and alleviate property-tax burdens for homeowners. Plus, crocs, pumpkin spice, and a Halloween surprise!