File picture of Jeb Bush. (Agence France-Presse)
He criss-crossed America on his father George H W Bush's successful 1988 presidential campaign, and as Florida governor he delivered the state's votes twice for older brother George W.
Following years in the political trenches for his family, Republican Jeb Bush is finally carving out his own path to the White House.
Should he prevail in his 2016 campaign, which he launched on Monday, Jeb would be the third Bush to occupy the top job as a Republican in a row, an achievement that would cement them as the most powerful dynasty in US history.
The pragmatic conservative will have to convince his party's base that he is in their corner, while maintaining sufficiently centrist positions to attract the independents needed to win.
Strongly pro-business and anti-abortion, the 62-year-old has vowed to be a "happy warrior" on the trail.
He has bucked party orthodoxy, making far-right voters wince at his support for immigration reform, controversial federal education standards and a theoretical willingness to hike taxes as part of a deficit-cutting deal - virtual apostasy in Republican circles.
Bush insists legalizing millions of undocumented workers is the immigration debate's "grown-up plan" - one that will fuel economic growth, unlike the mass deportations advocated by some hard-liners.
Fluent in Spanish, he is more analytical and methodical than his instinct-driven brother, more ideological and bookish than his father.
Bush, who backed the Iraq war but recognized "there were mistakes made" there during his brother's presidency, has also acknowledged potential pitfalls of running on the family name.
"Jeb is different than George, and Jeb is who he is," he asserted in a CNN interview in Estonia that aired Sunday at the end of a Europe trip.
"My life story is different."
Youthful indiscretions John Ellis Bush was born February 11, 1953 in Midland, Texas. It was an ivied upbringing, and teenage Jeb moved to Massachusetts to enter elite Phillips Academy, the same private prep school his father and brother attended.
This February he admitted to Huffington Post that "I drank alcohol and I smoked marijuana" at the school, where he was accused of bullying students and having scant interest in politics.
As part of a school program he travelled in 1970 to Mexico, where he met the love of his life, Columba Garnica Gallo. They were married at University of Texas, where Bush excelled as a student.
Bush got an early taste of international diplomacy in 1977 at age 24 when they headed to Caracas, Venezuela where Jeb worked as branch manager for the Texas Commerce Bank.
Bush volunteered for his father's 1980 campaign, then worked in real estate before being appointed Florida's secretary of commerce.
He campaigned full-time for Bush Sr in 1988, then unsuccessfully sought the governor's mansion in 1994, when his prudence overshadowed political savvy.
Asked what he would do for African-Americans if elected governor, Bush sought to stress equality of opportunity and answered: "probably nothing."
That year Bush, who was raised Episcopalian, turned to his wife's religion, Catholicism, and eventually converted.
"It's made me a better person," Bush told the New York Times in March.
Conservative governor He shifted from hard-charging ideologue to a more compassionate candidate in 1998, but ultimately went on a conservative tear during his 1999 to 2007 governorship.
Bush cut Florida taxes by $19 billion, privatized many state jobs, created the nation's first school voucher programs - later ruled unconstitutional - and intervened in divisive right-to-life cases, including that of a brain-damaged woman.
He also signed the controversial "stand your ground" law allowing people to use deadly force when threatened, and tightened his control over judicial nominations.
Bush governed Florida during the toxic 2000 presidential election that went down to the wire, ultimately in favor of his brother.
The US Commission on Civil Rights afterwards determined the process was riddled with faults, including "overzealous efforts to purge voters from the rolls."
Bush has not held public office for eight years. He quickly transitioned into the business world, apparently unapologetic in his determination to get rich.
He became an advisor to Lehman Brothers as the firm was on its last legs in 2008, and later to London-based Barclays.
He formed Britton Hill Partners in 2008 and managed BH Global Aviation, an offshore private equity fund which raised $61 million last September, largely from foreign investors, according to Bloomberg.
Bush joined Miami firm InnoVida as a paid consultant, but the building materials company went bankrupt in 2011 and its founder was jailed for fraud.
While Bush announced he has divested from all his business interests, his record will undergo intense scrutiny, like that of 2012 Republican nominee Mitt Romney, who made millions through his firm Bain Capital.
Last December Bush dismissed suggestions he was on a Romney-like venture capital path: "It's like comparing an apple to a peanut."