Before Jeb Bush was a likely White House contender, or the governor of Florida, or a wealthy real estate broker, a banker, a college tennis player or even a pot-smoking prep school student — before all of that, he was in the newspaper business.

Ten-year-old John Ellis Bush was co-editor of the “Neighborhood Round-Up,” a handwritten periodical he created with best friend Rob Kerr and distributed door-to-door for “only 5 cents” apiece in the wealthy Tanglewood subdivision of Houston. In the Feb. 23, 1963, edition, slipped discreetly between scribbled articles on new neighbors moving in and boyhood shenanigans, there was a news nugget of particular importance:

“Mr. Bush wins unanimously as head of Harris County Republicans.”

The fifth-grade scrawl marked what would become a landmark moment in the Bush family legacy: the launch of a political career that would land George H.W. Bush in the Oval Office. It was also a reminder that amid Jeb Bush’s carefree Texas childhood, the aura of political potential was always hanging over him. As George H.W. Bush's second son moved from Houston to Austin and back again, he was quietly honing the political chops that would lay the foundation for his own public ascent. And childhood friends and business colleagues in Texas say he did it with an unassuming relatability combined with the ability to stand out in a crowd.

Early Life in Houston

Jeb Bush was born Feb. 11, 1953, in Midland, which was rapidly expanding amid a West Texas oil boom. The family moved to Houston when Jeb was 6 years old, and he quickly formed a close group of neighborhood friends — the sons of businessmen and lawyers who were friends and colleagues of his father.

“We were with each other all the time,” said friend Jim Bayless. “All of our friends’ parents were collectively our parents. Any other parent had full disciplinary authority over kids that were not their own.”

Life in Tanglewood in the 1960s orbited around Jeb’s house and the makeshift baseball diamond in the backyard where the kids gathered after school. In little league and pickup games, Jeb, steeped in the famous Bush competitive culture, stole the show.

Jeb Bush, center, with younger brothers Neil and Marvin in 1961. Photo courtesy of the George Bush Presidential Library and Museum

“He was about the only one who could hit the ball over the fence, sometimes landing in the neighbor's pool,” Kerr said.

Jeb was an unusual combination of athletic ability. He threw right-handed and batted lefty, recalled his friend David Bates. He had long arms and quick feet, a powerful serve on the tennis court and a decent mid-range jumper on the basketball court.

But Jeb stood out for other traits that would become the building blocks of his professional and political persona.

“He was unfailingly polite and respectful,” Bayless said. “That’s just the way all those Bush kids were. It made the rest of us look bad.”

“He always stood out as being a little more serious, being a little more focused,” Bates said. “He never got into any trouble.”

A spokesman for Jeb Bush declined to comment for this story.

Kerr remembers Jeb’s reaction at a Houston Astros baseball game when the hometown crowd started booing centerfielder Jimmy Wynn because he was in a slump.

“Jeb sort of stood up and let the fans know they were not being very loyal,” Kerr said.

Against the Grain

The capacity to separate from a crowd — to do what he thinks is right instead of what everybody else is doing— could distinguish Bush from other likely GOP presidential contenders tossing red meat to the conservative base. At the 2015 Conservative Political Action Conference last month, Bush himself was booed by the audience when an interviewer mentioned Bush’s stances on undocumented immigration and Common Core education standards, which don’t exactly match the conservative canon.

“Over time, we have to start being for things again,” Bush told the audience. “If we share our enthusiasm and love for our country and belief in our philosophy, we will be able to get Latinos and young people and other people that you need to win.”

Some political analysts think Bush’s against-the-grain stance on those issues could be based on politics more than personal conviction.

“I don’t know if it’s authenticity so much as it is a calculation that a hard-core, comprehensive conservative will have a hard time winning" in a presidential election, said Larry Sabato, director of the University of Virginia Center for Politics. “You’re going to have much higher rates of participation by minorities and young people and other groups that tend to favor Democrats.”

Sabato said Bush could be trying to define himself even during the GOP primary “as a kinder, gentler Republican, to quote his father, or a compassionate conservative, to quote his brother.”

Jeb Bush (right) with George W. Bush (left), George H.W., Neil and Barbara Bush, holding Marvin, in Midland from about 1957. Photo courtesy of the George Bush Presidential Library and Museum

Such comparisons to his father and older brother, former President George W. Bush, have vexed Jeb Bush, who often has to remind crowds that he is his own man with his own ideas. But there are also those, mostly in wealthy circles, who show a great deal of loyalty to the Bush brand. It’s evident from talking to old friends and colleagues who heap endless praise on Jeb, George H.W. and the entire clan.

“There is no family that is classier,” Bayless said. “Everybody loves the Bushes.”

Bolstered by the vast Bush network of confidants and contributors, Jeb Bush is rapidly assembling a campaign machine that could also set him apart from other Republican contenders. In the 1960s, Jeb and his friends could name every player in Major League Baseball, Bates said. By 2015, he’s learned the political heavy-hitters, and how to play the field.

Life as a Longhorn

Jeb Bush left Texas at age 14 to attend boarding school in Andover, Mass., following the trajectory of his father and brother.

His time at the prestigious Phillips Academy was an aberration that largely consisted of bad grades, marijuana and apathy, the Boston Globe reported last month. But Bush has credited a study abroad trip his senior year to León, Mexico, where he met his future wife, Columba Gallo, with setting him back on the right path when he returned to Andover. He swapped drinking and smoking for writing letters to Columba and finished his last quarter at Phillips on the honor roll.

After nearly losing his way in New England, Jeb Bush passed on Yale — the old watering hole for college-age Bush men — and chose the University of Texas at Austin. Jim Bayless, Jeb’s Tanglewood friend, said all those boys felt a “strong gravitational pull” toward the university.

In Austin, Jeb lived in the new Dobie Center high-rise with Rob Kerr, David Bates and another friend. Kerr said they spent most of their free time hanging around the apartment complex, which had a swimming pool and a movie theater. The roommates played poker, set up miniature golf courses in the hallway, and listened to jazz and Taj Mahal records on their stereo.

Looking for some culture, they frequented a foreign movie theater across the street that showed films like Death in Venice and The Garden of the Finzi-Continis.

“I think we were aware of trying to grow as people,” Kerr said.

Jeb kept up with tennis, partnering with Bates to dominate intramural tournaments. The next year, when the varsity team needed a 12th player to make an even number, several members of the team recommended Bush to Coach Dave Snyder. After one practice, Snyder decided he could hang with the scholarship players.

Bush was added to the 1973 roster, listed as a 6-1, 165-pound sophomore. He didn’t travel with the team, but tallied four singles wins, five doubles wins and zero losses.

Even in tennis, Bush couldn’t escape his family legacy. One of his teammates said the Bush name might have helped him make the squad.

“Frankly, given his connections, the coach was happy for him to come out and participate,” said Dan Nelson, who spoke highly of Bush’s character and tennis ability. “I will admit that if he had just walked on as somebody without his family background, I doubt if he would have been a member of the team.”

Snyder said he didn’t know anything about the Bush family at the time, though he “found out pretty quickly.”

“He was good enough to be on the team,” Snyder said. “He probably had other things on his mind.”

Friends say those other things were school and Columba.

“It was clear that he was smitten,” Bates said. “He was in love with her and talked about her often.”

When it was time to work, Bush worked. The focus he discovered after meeting Columba in Mexico carried over from Andover. When his friends decided to rush fraternities, Bush stayed behind — he wasn’t interested in dates or parties, Kerr said. It took him less than three years to graduate magna cum laude with a degree in Latin American studies.

“He had a very good ability to study really intently while other people were goofing off,” Kerr said. “He was probably more studious than the rest of us.”

After a few years of constant phone calls and occasional visits, Jeb, 21, married Columba, 20, at the UT-Austin University Catholic Center in 1974.

Kicking Off His Career

Bush returned to Houston after graduation and took a job at Texas Commerce Bank. After a short stint as a loans officer, he was tapped to help set up an office in Caracas to manage hundreds of millions of dollars flowing out of the Venezuelan oil fields.

“We needed someone who spoke Spanish well, who had the ability to go into a situation with a lot of unknowns,” said Bill Arnold, vice president of the bank’s Latin America division at the time.

Still in his early-20s, Jeb picked up and moved to South America with Columba and their first two children, George P. and Noelle.

Jeb Bush in a Texas Commerce Bancshares Inc. advertisement in the May-June 1976 edition of the Alcalde, the University of Texas alumni magazine.

But Bush wasn’t fazed by the challenges of starting a new life with a young family in a foreign country, Arnold said. He described Bush as a “bundle of energy” and a fastidious money manager. When filling out expense reports, Bush left no stone unturned.

“I would say, ‘Jeb, we trust you on these $3 items. We don’t need diaper invoices,” Arnold said.

Arnold traveled across the continent with Bush hunting for new business. He recalled making cold calls together from a hotel phonebook, asking would-be clients to let Texas Commerce manage their energy portfolios. Bush had a knack for winning them over.

“He was very perceptive about people,” Arnold said.

At Texas Commerce, Bush developed one of the classic tools of the political trade: a wide range of relatability. At social functions with bank bigwigs and political VIPs like Lady Bird Johnson, Bush had a remarkable sense of poise for a recent graduate in his mid-20s, Arnold said, but he could also “get down with the folks” they met across Venezuela.

“He’s a people person,” said Dan Gramatges, a former senior vice president at the bank who dined with Jeb and Columba.

"He Was Just Kind of Matter-of-Fact"

To hear his friends tell it, Jeb Bush always stood out as a gifted athlete, a top student, a straight-talking people person, but it was never a big deal. His political promise was always there, but never in your face.

When Bush was in the Texas Commerce office in Houston in the mid-1970s, another banker named Bill Helms told Bush that his father — U.S. liaison to China at the time — would make a great president someday.

“I think he’d be interested in that,” Bush replied, to Helms’ surprise.

“Most people demur when you say something like that,” Helms said. “He didn’t boast. He was just kind of matter-of-fact. He was confident his dad could be president.”

It was the same Jeb who once scribbled, “Mr. Bush wins unanimously as head of Harris County Republicans.”

Ask Bush’s closest friends whether they thought he was destined to follow the trajectory of his father and brother — a bid for the White House — and they all say pretty much the same thing: They had no clue at the time, but looking back it makes perfect sense.

Bush left the bank to work for his father’s 1980 presidential campaign. Afterward, he settled in Miami with his family, entered the real estate business and made a small fortune. His foray into politics mirrored his dad’s — Republican Party chairman in Dade County. Bush later served as Florida’s secretary of commerce and, eventually, its governor.

Rob Kerr and David Bates have followed Jeb’s rise from the backyard ballpark in Tanglewood to the Governor’s Mansion in Tallahassee, from hawking 5-cent newspapers to cold-calling customers in Venezuela to the biggest sales pitch of his life — a bid for the presidency.

“We’re very happy for what he’s achieved,” Bates said. “But neither of us are entirely surprised how well he’s done.”

Jay Root contributed to this report.

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