Mr. O’Rourke spent much of the last two months of 2018 finishing his work in Congress, condensing his preparation period even more tightly. In recent weeks, though, he has done some of the more typical work of a politician considering a run for president: conferring with longtime staff and others who he hopes might join his cause; speaking to key groups, like a conference of Hispanic leaders in Chicago and gun control advocates in his hometown; headlining a rally to counter Mr. Trump’s call for a border wall when the president appeared in El Paso.
But his indecisiveness has compelled some veteran Democratic aides who admire him to accept positions with other candidates. Several people who have spoken to his team came away questioning whether Mr. O’Rourke was thoroughly prepared for the crush of a national race. Some suggested he lacked detailed plans like a comprehensive strategy for amassing delegates. (Mr. O’Rourke and his advisers have, however, spoken to campaign veterans with experience in managing the delegate process about possibly joining his team, according to a person familiar with the discussions.)
Unlike other candidates who recruited staff members over the past year with a wink and a nod — all but sure that they would enter the race — Mr. O’Rourke was still conveying uncertainty as recently as last month, according to the people who spoke to him.
Since then, he has sounded firmer.
“I think he feels his time is now,” said Randi Weingarten, the president of the American Federation of Teachers, who met with Mr. O’Rourke at length recently.
Ms. Weingarten, speaking with Mr. O’Rourke and his wife, Amy, in El Paso, raised the possibility of Mr. O’Rourke’s challenging Senator John Cornyn in 2020.
Texas Democrats have prodded him on this score as well, but few expect Mr. O’Rourke to confine his ambitions to another state-level race. After prolific success with small-dollar donors during the midterms, Mr. O’Rourke is likely to have little trouble raising enough money to get a presidential run off the ground. His presence could energize some crucial voting blocs, like young people, who formed much of his coalition in Texas.
“If he got in, it would be a pretty big game-changer,” said Eliana Locke, who leads the College Democrats at the University of Wisconsin-Madison, where Mr. O’Rourke met with students last month.
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