But for all the charisma and fundraising that could carry him far into the Democratic primary, a series of missteps in his campaign’s earliest days served as a reminder of how uncertain a prospect his star remains.

“For all the fanfare, the band was playing a pretty flat tune,” Dave Nagle, a former congressman and Iowa state Democratic Party chairman, said after watching O’Rourke address a large rally from the bed of a red Ford Ranger in Waterloo, Iowa. “There’s just no substance to it.”…

On the eve of his campaign announcement, O’Rourke personally apologized to a prominent Democrat in Iowa for his campaign’s lack of organization there, attributing it to late decision-making and a skeletal staff, according to a source familiar with the conversation. Hosts of multiple events in Iowa said they were informed unusually late about logistics, especially given the large crowd sizes O’Rourke could command. And with O’Rourke’s small staff focused intently on Iowa, Democratic activists in at least two other states, including New Hampshire, said calls they were told to expect from the campaign never came.