Boxed in by a base enamored with Trump that has instinctively rallied to the former president’s defense, DeSantis has struggled for months to match the hype that followed his landslide 2022 reelection. Ryan Tyson, DeSantis’ longtime pollster and one of his closest advisers, has privately said to multiple people that they are now at the point in the campaign where they need to “make the patient comfortable,” a phrase evoking hospice care. Others have spoken of a coming period of reputation management, both for the governor and themselves, after a slow-motion implosion of the relationship between the campaign and an...