Shane Goldmacher is a political reporter covering the 2016 presidential race. Daniel Lippman is associate editor for states and reporter for Politico.

Five years ago, as Ted Cruz plotted his path to the U.S. Senate, the anti-establishment crusader sought a private audience with and the backing of one of the faces of the modern GOP establishment: George W. Bush.

In a never-before-reported meeting in Bush’s Dallas office, Cruz began to outline his 2012 campaign playbook for the former president, according to people familiar with the conversation. Cruz explained how he would consolidate conservatives yearning for a political outsider, how he would outflank the front-runner on the right, how he would proudly carry the mantle of the ascendant tea party to victory over entrenched elites.


It was impressive foreshadowing. But Bush cut Cruz off before he could finish.

“I guess you don’t want my support,” Bush interrupted. “Ted, what the hell do you think I am?”

If the idea of a private meeting between Bush and Cruz seems strange now, it was not so odd at the time. While Cruz is running for president in 2016 as the consummate outsider, he launched his political career as a Bush administration insider, and his relationship with the GOP establishment is far deeper and more complex than he lets on.

On the trail today, Cruz bashes the “Washington cartel,” jokes of being so hated in the U.S. Capitol that he needs a “food-taster,” and says at nearly every stop, “If you see a candidate Washington embraces, run and hide.”

But 16 years ago, as a young domestic policy adviser for Bush’s 2000 campaign, Cruz himself had sought Washington’s embrace. He’d uprooted his life, taken an 80 percent pay cut and moved to Austin, Texas, with visions of a big, important White House job to follow.

Almost from his arrival at Bush’s headquarters, colleagues say Cruz flashed many of the same assets and liabilities still on his political balance sheet: acumen and ambition, combative and conservative instincts, elbows as sharp as his smarts, a knack for self-promotion and rubbing colleagues the wrong way.

When Bush won, however, Cruz would not get the White House post he had dreamed of; instead, he found himself in the bureaucratic backwater of the Federal Trade Commission. “Through mistakes of my own, I put the fault nowhere other than myself, I burned some bridges on that campaign,” Cruz told Politico in an interview. “I chalk it up to youth and immaturity.”

“It was a difficult chapter when you poured your heart into something for two years and the desires of your heart are denied. That’s hard. And particularly when you’re seeing so many of your friends rewarded.”

The snub marked a crucial inflection point in Cruz’s career, one that led the young lawyer to soon give up on Washington. In just over two years, he’d move back to Texas where he would reinvent himself as solicitor general and climb the political ladder anew, this time as a fire-breathing, tea-partying, anti-Washington insurgent.

“Not getting the job made him angry. But what it allowed, in a quirk of history, is it put him in the right place when the country got angry, also,” said a veteran of the Bush 2000 operation who, like most of the nearly two dozen people interviewed for this article about Cruz’s time in the Bush orbit, spoke on condition of anonymity. “He would not have had this moment if he began in the White House [then]. That ended up being a gift to him. He saw his moment when it came.”

That moment appears to be now. Powered by the Republican electorate’s disgust with the GOP elite that had rejected him 16 years ago as a junior staffer, Cruz is on an outsider’s course that has led him to enter next week’s Iowa caucuses in a virtual tie for the lead. But that is, he hopes, only the first stop. The final goal is the prize that eluded him as a young man: the White House.

Cruz had arrived in Austin with the sterling résumé of a Republican insider on the rise. He’d gone to Princeton, been a national debate champion and graduated from Harvard Law. He’d clerked for William Rehnquist, the first-ever Latino clerk for a chief justice of the Supreme Court. He’d taken a job in a connected boutique D.C. law firm, where one of his early clients was none other than future House Speaker John Boehner.

It was all part of Cruz’s master plan. He’d intended to be president since he was at least a teen. In high school, he wrote a frightfully prescient bio for himself that outlined his plans to go to Princeton (check), Harvard Law (check), have a “successful law practice” (check) and then “pursue his real goal—a career in politics.” The Bush campaign was the logical next step. "Ted would like to run for various political offices and eventually achieve a strong enough reputation and track record to run for—and win—President of the United States," Cruz wrote as a senior in high school.

Ted Cruz's bio in a program for the Constitutional Corroborators, a troupe of high school students who traveled across Texas to recite portions of the Constitution. | Credit: Laura Calaway

By the summer of 1999, Cruz wasn’t yet 30 but his CV was already overflowing.

On the 2000 campaign, Cruz’s portfolio was domestic policy, everything from legal issues to immigration to campaign finance. Coworkers said Cruz was more conservative than most on the team, often agitating to take harder right positions. "He was the chief propeller head," said Mark McKinnon, who was Bush's chief strategist on the campaign. "He was the smartest guy in the room, who had a lot of confidence. But that was a good thing. You want that in your research team."

Added McKinnon, "He leaned in."

But Cruz, almost from the start, leaned in too far. Several 2000 colleagues recalled how Cruz would position himself prominently whenever a national news outlet came to town. When the Washington Post’s Style section wrote about why the campaign was based in the liberal enclave of Austin, it was Cruz who gave the Post reporter a tour of the headquarters.

When another Post reporter, now columnist Dana Milbank, came to profile the Bush campaign's young bucks, Cruz eagerly volunteered himself. "When I mentioned this self-promotional effort to a senior Bush adviser," Milbank recalled in a column more than a decade later. “I received a knowing eye-roll in response.” Milbank decided to profile someone else.

“It struck me that he was all pure unbridled ambition,” Milbank recalled in a recent interview. “I picked up a guy who would use whatever means necessary to get on top. He was like, ‘No, I’m the guy you should be writing about.’ I guess, in retrospect, he was right.”

Cruz kept in touch anyway. “He would send out, at fairly regular intervals, these email updates on his triumphs and conquests,” Milbank said.

Some 2000 colleagues questioned Cruz’s work ethic. “He acted like he was smarter than everybody and because he was that, he didn’t have to work as hard,” said one Bush 2000 veteran. Said another, “He didn’t make a lot of friends, but I found it mostly driven by the fact he didn’t carry his fair share of the work. In fact, he was downright lazy during the campaign.”

Ted saw the bright lights of the White House and wanted them to shine on him,” Fleischer said.

About a half dozen of Cruz’s campaign colleagues specifically recalled him leaving work around 5 p.m., only to return late at night to send off emails to senior campaign officials. In an era before everyone had smartphones, they said, the aim seemed clear to them—he was trying to make it look as if he’d been working continuously.

“Simply not true,” Cruz told Politico. “I was typically there very late at night, almost every day. I mean there were a lot of nights where I’d go home 1, 2, 3 o’clock in the morning.”

But Cruz acknowledges he made mistakes. “Listen, I am neither the first nor the last person to learn lessons when you’re young,” he said. “And maturity and humility are two of the most important lessons that most young people need to learn, and I certainly needed to learn.”

Ari Fleischer, who would go on to become White House press secretary, called himself “one of the few people in Bush world who likes” Cruz. “I always found Ted to be affable, self-deprecating, smart and enjoyable to be around,” Fleischer said. But he still said that Cruz had carved out a debilitating reputation for himself internally.

“Ted saw the bright lights of the White House and wanted them to shine on him,” Fleischer said. “He was young, extremely smart and ambitious, and he wasn’t the first and won’t be the last to misplay his cards and try to walk into that building. And in an environment where teamwork and modesty was prized, Ted didn’t fit that mold.”

Others said Cruz was known for trying to angle additional time with Bush, both on the trail and at the governor’s mansion, where the policy team would brief Bush in private sessions. “He was not a bad guy. It all just was someone looking for face-time with the then governor,” said a third 2000 campaign aide. “It just seemed so much more obvious when he does it. He lacks a subtlety that a lot of other people bring. He makes it feel like he wears his ambitions on his sleeve.”

Said a fourth Bush adviser: “Climbers like that really stood out and mostly got made fun of. They were people who were never really able to work their way into the inner circle.”

Rick Tyler, a Cruz spokesman on the 2016 campaign, dismissed all the complaints as unimportant. “That’s the trivial things petty people say when you’re trying to diminish someone,” Tyler said.

As for Bush himself, he took to calling Cruz, “Theodore.”

“Perhaps because I came off as super-serious,” Cruz wrote in his 2015 autobiography, A Time for Truth. “I don’t know if he assumed that was my full name, which it is not, but it didn’t really matter for his purposes.”

***

By the Thursday after the election, Cruz was on a plane to Florida to join Bush’s legal team. To hear Cruz tell it, he was indispensably in the middle of the historic recount. He slept only seven hours in the first six days in Florida. “It was one step shy of utter chaos,” he wrote in his book. “I should know, because I helped manage the process.”

That’s not how everyone remembered his role. While those involved say Cruz was a part of the legal team, he was not at its epicenter.

“I have no recollection of working with him or ever seeing him involved in the process,” said Barry Richard, who was the Bush campaign’s lead counsel in Florida. With Cruz now running for president, Richard has gone back to his files to search for Cruz’s name. “I finally found one book that noted that he had been working for Ted Olson and he had some work on some briefing or something,” he said. Richard is a Democrat, as he was in 2000, and he is married to the chair of the Florida Democratic Party, though not active in partisan politics himself.

“The people who managed the process were James Baker, Ben Ginsberg and George Terwilliger. Period,” Richard told Politico. “I never talked to anybody else as far as managing the process was concerned.”

In fairness, Cruz was definitely involved. (Nicolle Wallace, who would go on to serve as Bush’s press adviser, remembers Cruz. As she said on Bloomberg TV last month, “The recount, was sort of ground zero for the biggest egos in both parties—in the whole country—and he rose to the top in terms of hubris and egomania.”) Among other tasks, Cruz recruited future Supreme Court Chief Justice John Roberts to join the Bush legal team. And when the high court’s final and historic ruling in Bush v. Gore came down, Cruz was in the Bush legal team’s headquarters poring over the ruling and was the first to inform Baker that they’d won.

By then, Cruz was already angling for a top administration job, in particular he’d mused to colleagues back in Austin that he could see himself as White House counsel.

Soon after that December victory, future Bush chief of staff Andy Card asked soon-to-be White House counsel Alberto Gonzales to interview some of the lawyers on the Bush campaign, including Cruz, for positions in the White House counsel’s office.

According to a person familiar with the process, Gonzales interviewed Cruz and then offered him an associate counsel job. Cruz instead asked to be deputy counsel, but that job had already been filled.

“While Cruz’s credentials were impressive, they were certainly no better than most of the lawyers who eventually worked in the office," this person said. Other lawyers who were named associate counsel had not only clerked on the Supreme Court, as had Cruz, but also had made partner in prestigious law firms, worked on Capitol Hill and had experience with investigations—all experiences Cruz did not have.

Rather than taking the associate position offered, however, Cruz walked away when denied the deputy job.

Ted Cruz stands in the background to the right during a Bush v. Gore hearing in Tallahassee, Fla. on Dec. 3, 2000. | Vincent Laforet/The New York Times/ Redux

Asked about the jobs he had been offered after his work on the Bush campaign, Cruz declined to discuss specifics. “I was proud to have the opportunity to be on the campaign, and, as I described in my book, I hoped to have a meaningful position in the White House,” he said. A Cruz spokesman later said the senator does not remember ever being offered a job.

Explained Fleischer: “Ted’s bosses were very put off by him and by how ambitious he was. And that’s why Ted got basically put in an agency very far from the White House during the transition.”

***

Some of the most introspective passages from Cruz’s autobiography are about his failings on the 2000 campaign. “It was a crushing blow,” he writes. The following two years were the hardest of his life. “Going through that experience altered my personality and forced me to view the world differently, to treat others with greater respect and humility. It was a lesson I very much needed to learn.” Both in his book and to Politico, Cruz called it a gift. “You know, I quote the terrific country western song, ‘Some of God’s greatest gifts are unanswered prayers.’”

Indeed, what had then seemed like Cruz’s biggest professional setback has proved to be one of his biggest assets in 2016. Not joining the Bush White House ensured Cruz would not be weighed down by any of the administration’s big-government baggage—the expanded federal debt, the bank bailouts, the Medicare expansion, the Iraq War. Or Bush’s later push for a comprehensive immigration overhaul, including allowing those here illegally a path to citizenship (Cruz helped pen Bush’s 2000 immigration position, which notably did not include any kind of “amnesty.”)

“I don’t know how the future plays out if he ends up going in as a top Bush aide, whether or not he is able to take the trajectory he takes,” said Chip Roy, who served as Cruz’s first chief of staff in the Senate. “That’s those unanswerables in life.”

But if Cruz says the 2000 experience humbled him, his old Bush colleagues don’t seem to have noticed. “If that was the lesson he learned, it does not seem like he learned it very well,” said one of his Bush 2000 coworkers. “It just seems the person that I knew in 2000 is the same person that I would see on the Senate floor.”

Many of Cruz’s congressional colleagues have as little nice to say about him as his Bush era associates. He’s been called the most hated man in the Senate, a “wacko bird” and a “jackass.” Sen. Lindsey Graham recently compared the thought of choosing between Cruz and Donald Trump in 2016 to being “shot or poisoned. What does it really matter?” Perhaps as telling as their comments are their actions; none of Cruz’s Senate colleagues have endorsed his presidential bid.

“Not one Republican senator has endorsed Ted Cruz. I mean, when you think of it, that's actually a shocking thing to believe,” Trump said Sunday on Meet the Press, part of his ongoing effort to thrust Cruz’s personality to the center of the campaign.

Tyler, the Cruz strategist and spokesman, argues that Cruz is hated by exactly the right people. “Just because the Senate doesn’t like him, because he hasn’t assimilated to go along to get along, doesn’t meant the voters don’t like him,” Tyler said. “If he is not liked by senators in this race, that is not a problem.”

Cruz routinely scores among the highest favorability ratings of the 2016 field among Republicans voters, propelling his rise to the top of the polls in Iowa and second nationally. On the trail, he wears Washington’s loathing as a badge of honor.

But Cruz visibly bristled when Politico asked about similarities that people have pointed out between the Cruz of 2000 and today.

“The situations are not remotely comparable,” he said, pausing for 12 seconds to gather his thoughts.

Cruz speaks during a campaign stop at the library in Onawa, Iowa, in early January. Cruz is polling at second according to the latest polls out of the Hawkeye State, with a thin margin between him and the frontrunner, Donald Trump. | AP

“In my 20s, I was a young cocky kid and that understandably rubbed people the wrong way,” Cruz continued. “In my 40s, in the Senate, I have consistently treated every member of the Senate with respect and civility. What has dismayed Republican leadership is not how I treat others, it is rather that I insist on honoring the commitments I made to the men and women who elected me.”

The fact that Cruz casts his Senate agenda—pushing the 2013 government shutdown in an effort to stop implementation of Obamacare and forcing Republicans to vote to raise the debt ceiling in 2014, to name two episodes in particular—as fulfilling campaign promises to the people is part of what so irks Washington Republicans. In both those cases, the overall GOP brand suffered, but Cruz’s stature among the base rose.

“If you’re in the club in Washington and there’s somebody like Sen. Cruz who’s going to talk directly to the people and go over, go around the club and go straight to the people, the club still takes offense to it,” said Roy, his former chief of staff.

Trump has relentlessly tried to make Cruz’s likability a differentiator as voting in Iowa has neared. “I get along with people. Ted cannot get along with people at all,” Trump said Sunday. “I mean, the biggest problem he has, he's a nasty guy and nobody likes him.” Other, less bombastic Republicans have sounded the same alarm. “I don’t know how he’s going to deal with Congress,” 1996 GOP presidential nominee Bob Dole told The New York Times. “Nobody likes him.”

That apparently includes Bush himself. At a fundraiser for his brother, Jeb, last October, George W. Bush gave voice to what so many of his old campaign hands have long snickered about Cruz, “I just don’t like the guy.”

***

Cruz wouldn’t talk about what was said when seeking W.’s backing for his first Senate run. “I don't believe I’m at liberty to do so,” he told Politico. “I sought out the meeting and traveled to meet with him as a show of respect. I spent a number of years of my life working for George W. Bush and poured a great deal of time and energy and effort to helping him get elected and to help him win the recount battle in Florida so that he could serve as president.”

“Politics is about addition,” Cruz said, “and I am happy to welcome anyone’s support, then or now.”

But Cruz, the 2016 outsider, has done precious little to court insider support from the GOP establishment that he once wooed as a young staffer. One of his favorite stories to tell on the stump is that The New York Times predicted, on the day he announced his 2016 campaign, he couldn’t win the day because, in Cruz’s telling, “the Washington elites despise him.” Cruz pauses for dramatic effect before bellowing his punch line: “I kinda thought that was the whole point of the campaign!"

The crowds inevitably laugh. But one of Cruz’s former coworkers on the Bush campaign said the dislike is real and forthcoming, especially from those who know Cruz best. “The longer you’ve known him,” this person said, “the less likely you are to support him.”

Still, the operative marveled at how Cruz had overcome Bush-world setbacks that would have crippled most people’s careers. “The guy’s running for president,” the Bush veteran said. “That’s a lot of further than the rest of us.”