“We never had a formal sit-down conversation or a checklist. But we’d been talking about it off and on,” O’Rourke said. “I just turned to her and I said, ‘Is this what you want to do?’ She said, ‘Yeah. Is this what you want to do?’ I said, ‘Yeah.’ And it just felt good. We were both in the same place.”
That conversation concluded a months-long process of introspection, both public and private, that led to O’Rourke’s announcement last week that he would run, attempting to leverage a 2018 Senate loss into a national movement. The decision sharply contradicted some of his earlier Shermanesque statements that he wouldn’t run, comments in which he spoke openly about how, as a father, he couldn’t fathom the damage another campaign would impose on his family.
Interviews with some of those closest to him provide a window into a decision-making process that was organic and haphazard, one that involved a coterie of informal advisers and longtime friends and allowed thoughts to simmer before making a gut-level call. It is a process that informs how he will run his freewheeling and by-the-moment presidential campaign, as well as how his White House would operate if he were to get that far.
In the first days of his campaign he has outlined the issues motivating him — combating climate change, fixing the country’s immigration issues and healing its racial divides — but he concedes he doesn’t have some of the specifics and says he will lean on “people far smarter than me.” Unlike candidates such as Bernie Sanders and Elizabeth Warren, who launched their campaigns with clearly articulated policy platforms, O’Rourke focuses more on sweeping calls for unity and pitching himself as the best antidote to the country’s toxic politics.
“We want to be for everybody, work with everybody,” he said. “Could care less about your party affiliation or any other difference that might otherwise divide us at this moment of truth, where I really feel we will either make or break this great country and our democracy.”
When he pondered a presidential race, Republican Mitt Romney developed long lists of pros and cons, scribbled on a legal pad, and met with his entire family to give everyone a vote in the matter. As he looks at a Democratic run, Joe Biden has been agonizing with aides and advisers for months, holding conversations with his children and his grandchildren.
Little of that occurred with O’Rourke. There were no formal sit-downs with the children, even though there were plenty of conversations with them. The call was instead the result of a series of talks among a married couple and a trio of trusted advisers, all culminating in the morning chaos of the O’Rourke household.
“If there was a moment, that was the moment,” O’Rourke said. “I know it’s not dramatic or even interesting. But it kind of happened to be one of those moments where we get to talk to each other.”
'We need to be together'
Throughout his 2018 campaign in Texas against Sen. Ted Cruz (R), O’Rourke would talk about the difficulty of missing family events at home. During speeches, he would announce the scores of the children’s baseball games he was monitoring on his phone. In the final days of the campaign, he appeared on “60 Minutes” and insisted he would not run for president.
“I don’t want to do it. I will not do it,” he said. “We spent the better part of the last two years not with each other, missing birthdays and anniversaries and time together. Our family could not survive more of that. We need to be together.”
“I’m completely ruling that out,” he added. “Win or lose, I’m not running in 2020.”
His advisers now say that he was so emphatic because he adamantly believed he was going to win the Senate campaign. The loss was crushing, but the day after, the O’Rourkes had friends over for breakfast and started to contemplate what might come next.
Just about everywhere he went O’Rourke was encouraged to consider a presidential run. TMZ, the celebrity-tracking news site, had begun interviewing him at airports. Democratic operatives were cold-calling, asking to set up meetings.
And President Barack Obama had him to his office in Washington, where they discussed the rigors of a presidential campaign and the effect on the Obama family.
“I want to make sure I don’t leave the impression he in any way encouraged me,” O’Rourke said of his meeting with Obama.
O’Rourke’s family, though, took away a key lesson: The Obama family spent more time together in the White House than they had in the previous years.
As his congressional term ended, O’Rourke still held his monthly town halls, the ones his staff assumed they were canceling. He often went to the Tornillo detention center outside El Paso, which was overflowing with undocumented minors who had been apprehended at the border.
After he left office Jan. 3, O’Rourke and his wife began holding frequent conference calls with his three closest advisers — Cynthia Cano, his road manager; Chris Evans, his communications director; and David Wysong, a longtime friend who ran his House office, helped manage his Senate race, and had been talking about O’Rourke running for president for some time.
Wysong began attempting to build the framework of a campaign in case it was needed. Evans and Cano sifted through a barrage of emails.
For O’Rourke, the presidential run was part of the discussions, but he batted around other ideas. Some friends floated being a professor. Others thought he could become the next president of the University of Texas at El Paso. Senate Minority Leader Charles E. Schumer (D-N.Y.) frequently called O’Rourke’s cellphone, urging him to consider running in 2020 against Republican Sen. John Cornyn.
By the end of January, O’Rourke’s advisers flew to El Paso for more face-to-face meetings. Evans parked himself in a $49-per-night Airbnb property.
O’Rourke was weighing not only whether to run for president, but how. His Senate race had a small, tightknit team — no pollster and no speechwriter — that largely consisted of O’Rourke driving around the state. Could they keep that same feel in a presidential campaign?
“He does want to stay true to himself, and that can be hard with these different orbits,” said Mike Stevens, who has been close friends with O’Rourke since they met at basketball camp and later formed a band. He added, lightheartedly: “This is the Gen X burden, that Gen X must bear.”
In February, O’Rourke traveled to New York for an interview with Oprah Winfrey. She practically begged him to run. And he showed more enthusiasm for getting into the race than he had before. He publicly committed to making a decision by the end of February, something that he and Amy had privately discussed but not something he meant to say aloud.
“Here’s the thing: He thrives off people and energy,” said Steve Ortega, a longtime friend who served with O’Rourke on the El Paso City Council. “And 99 percent of the people he talked to, including myself, were telling him, ‘You should run and here’s why.’ He wasn’t hearing a lot of, ‘No, Beto, you shouldn’t do it and here’s why.’ He genuinely excites people.”
A rolling family dialogue
The family, meanwhile, had reconnected, O’Rourke said. When he was a member of Congress, he would spend only weekends at home. When he campaigned for Senate, he traveled for weeks at a time.
“Amy, what she wanted to do is make sure we just hung out as a family,” O’Rourke said. “That was awesome. I don’t know what in that process of just hanging out opened us to doing this together. But I think it was necessary before we could be able to even consider doing this.”
The possibility became a rolling dialogue in his house, part of the domestic routine.
The children — Ulysses, 12; Molly, 10; and Henry, 8 — began offering their opinions on the race. Ulysses had suffered during the long stretches apart. But when O’Rourke asked his son if he should run, “He said, ‘Yeah. There’s too much going on right now.’ ”
“Molly was like, whatever you want to do,” O’Rourke said. “She was like, ‘I didn’t want to be the one to push him into doing this. I wanted him to do what he thought was right.’ . . . And Henry, Henry seems open to it.”
When a Vanity Fair reporter talked to O’Rourke’s family in early February, Henry told his father that he would cry all day if he ran for president.
“Just the one day?” O’Rourke asked.
“Every day,” he replied.
Rationale for running
If any event persuaded O’Rourke to run, it was one held by the president. When President Trump came to El Paso on Feb. 11 for a rally at the border, O’Rourke appeared at a counter-rally. He fed off the large crowds — the turnout rivaled the president’s — and the ability to tell a story about his native city and its bicultural nature.
O’Rourke, a punk rock musician and businessman before getting into local and then national politics, insisted that he has not had lifelong aspirations to run for president. He’s been arrested twice, once for a DUI, and had a negligible record as a three-term congressman.
“It’s not one I have contemplated until fairly recently,” he said during the taping of a podcast Friday night in Cedar Rapids, Iowa. “And you can tell from my life that it’s not been organized towards this destination.”
After he finished brushing his teeth a few weeks ago, his advisers began planning his announcement trip. Last week, they called people in southeastern Iowa, asking if they would host a house party for an unknown candidate. Being Iowans, they said yes.
When O’Rourke arrived in Keokuk, a struggling town near the Mississippi River, he was driving a minivan, his handful of aides riding along.
That night in Muscatine, he cited his family as a rationale for running.
“I think they have something to add to this,” he said. “And my country, my kids, our future depends on every single one of us doing every single thing we can. And for me, that’s running for president.”