From the beginning of his candidacy last June, he pledged to run with "joy" and adopted a tortoise-and-the-hare strategy, earnestly believing that he would prevail in the end despite a crowded field of candidates.
Even as his chances became grim over the past eight months, he started handing out tiny toy turtles from his pockets to children, telling them that "slow and steady wins the race."
But in 2016, "slow and steady" was the opposite of what the country wanted.
There's plenty of blame to go around for Bush's fall, but the central theme is the failure to read the mood of the GOP electorate that was angry and wanted change. Voters responded to Donald Trump, who Bush both underestimated and whose appeal he didn't understand.
Bush was out of practice on the campaign trail, something evidenced by his early stumbles answering questions on his stance on the war in Iraq -- a question that should have been anticipated with an answer ready. He declared early he was his "own man," but also highlighted his connection to his father and brother, presidents both. And he raised over $100 million between his campaign and super PAC, but it didn't scare anyone out of the race.
In the final few days before the South Carolina primary, Bush started to realize that his White House bid might be coming to an end. He talked with less certitude about moving on to other states and appeared almost wistful at times.
But it wasn't until late Saturday afternoon that he knew that he likely wouldn't be moving forward, according to campaign aides. Many staffers were told of his final decision just five minutes before he took the stage at the Hilton in Columbia.
"In this campaign I've stood my ground refusing to bend to the political winds," Bush said Saturday night. "We put forward detailed, innovative conservative plans to address the mounting challenges that we face. Because despite what you might have heard, ideas matter ... policy matters."
Bush spent much of his campaign focusing on his experience as governor of Florida and policy, consistently rolling out new initiatives and plans. But 2016 was simply a different era from the last time he ran for office -- in 2002.
Bush adviser Sally Bradshaw told CNN Saturday night that 2016 simply "was not his year."
"Look, this was a year that was bigger than a lot of the candidates in this race," Bradshaw said. Bush "didn't equivocate, and he took on Donald Trump and he showed us what is best about our party and what is best about our country."
As CNN's embedded reporter with the Bush campaign, I followed the former Florida governor from the lofty moments, early in 2015 when he was preparing for his presidential run, to the final days when he acknowledged that he would not be the third Bush to work in the Oval Office. I covered him at more than 100 events in 14 states over 11 months and this story is based on that experience.
On paper, an ideal candidate
Bush, who turned 63 last week, never placed above 18% as a candidate in the polls, but he remained the front-runner in the GOP field for the first month of his campaign.
He was a candidate who fulfilled what Republicans thought they needed after the 2012 election loss: an experienced governor from a swing state who could help expand the Republican base by appealing to Latinos and craft a narrative of a more compassionate party.
By the middle of the year, his campaign and allies at the super PAC Right to Rise USA, had raised more than $100 million, far more than any other candidate. The haul was meant to send the message that Bush could dominate the field and be a formidable general election candidate.
But instead, 2016 appeared to be the election no one said no to running. From Bush's one-time protégé from Florida Marco Rubio to Govs. Chris Christie, Bobby Jindal and Scott Walker and former Govs. Mike Huckabee and Rick Perry, Bush's cash scared no one. And it turned out to be for good reason.
Then, a perceived sideshow candidate named Donald Trump -- who labeled undocumented immigrants as "rapists" in his announcement speech -- stole the show. He started to gain traction and within weeks became not only the front-runner, but took the lead and ran away with it.
The surge revealed a Republican electorate that was more angry than joyful, surprising the Washington political class and upending the Republican primary narrative. With every insult hurled, Trump's anti-establishment, verbose persona became more popular. It was clear that Bush would face an uphill battle.
And Trump had his sights set on the former governor. He quickly began mocking Bush as an "unhappy person" with "low energy." Like many of the other candidates, Bush's campaign tried to stay above the fray and not engage with the reality TV star.
In Henderson, Nevada, in late July -- one of the first times Bush was asked to respond to Trump's "rapists" comment -- the candidate simply said: "I disagree with him." Pressed for more, he replied curtly: "I think he's wrong.
A couple of weeks later, in Carson City, Nevada, when Bush was asked if he wanted to respond to Trump accusing him of promising favors to his donors, Bush looked this reporter in the eye and said: "No."
Bush didn't start hitting back at Trump's accusations that Bush was "low energy" until mid-September, but by then it was too late. The label had stuck.
Aides, advisers and even Bush, himself, have quietly acknowledged that the popularity and influence of Trump was underestimated at the beginning.
"People probably thought they could just let (Trump's) comments go into the ether, not take the bait," one adviser said. "This campaign probably felt for some time that it was best to let Trump hang out there and make a fool of himself."
Messages didn't stick
Bush, from the start, had high name recognition, but the campaign felt that people didn't know his conservative record as the two-term governor of Florida.
But those messages couldn't drown out the barrage of attacks coming his way from Trump, especially the "low energy" brand that quickly became the meme of Bush's candidacy.
"I believe it hurt a lot," the adviser said.
It was especially frustrating for the campaign because, Bush, in fact, was anything but low energy. He campaigned tirelessly from the start of his bid and voters were routinely impressed and surprised by his passion when they saw him at his town halls.
But, having been out of campaign politics for more than a decade, Bush struggled early on to command the stage at debates and appeared awkward on TV, versus the looser, comfortable-in-his-own skin Bush that voters saw in person.
Over that time, Bush gradually stepped up his attacks against Trump, and at a debate in December, Bush tore into the front-runner repeatedly, solidifying himself as the "anti-Trump" candidate. Trump's locker-room language irritated Bush so much that the former governor started calling Trump a "loser" and a "jerk," and painted him as a disparager of Hispanics, women, people with disabilities and prisoners of war.
Even though Bush had fallen so far behind in the national polls -- he's been in the single digits since October -- Trump continued to pillory Bush, and their feud manifested itself in daily attacks in stump speeches and over Twitter.
Meanwhile, fingers started pointing. As Bush's campaign continued to struggle before the primary season started, donors and supporters were already starting to blame the super PAC and its chief, Bush confidant Mike Murphy, for not focusing hard enough on Trump and targeting other rivals like Rubio, instead.
Bush himself never denounced the ads put out by the super PAC but tried to keep as much distance possible from the group that he spent the first half of 2015 raising money for. During his campaign, he expressed frustration over the super PAC process and blamed the Citizens United ruling for making campaign finance so complicated -- not because too much money was being spent, but because it meant so much was out of the control of the actual candidates.
Bush eventually saw more and more support for his offensive against Trump. At his last event in South Carolina, he received a standing ovation when Sen. Lindsey Graham, who campaigned for Bush in the final month, thanked Bush for "standing up for just being decent."
Early stumbles on Iraq
Advisers, donors and Republican strategists say Trump wasn't the only factor that led to Bush's decline.
He stumbled even before he was a candidate when he failed to answer a question
about the Iraq war last May -- a blunder that took Bush a week and multiple attempts to get right.
The episode alarmed donors and highlighted a level of Bush fatigue that the country was still feeling. While the campaign earnestly believed that Bush would have plenty of time to define himself and distinguish his candidacy from that of his brother or father, that never fully happened.
One year ago, he declared "I am my own man."
But he then went the other way, bringing himself closer to his family and started using his "front row seat" to the presidencies of his brother and father as "unique" foreign policy credential. Nothing seemed to quell the concerns of a third Bush presidency, which voters continued to raise at town halls even until the end.
"What we're seeing right now on both sides of the aisle is the country is not rushing to have a repeat of Bush vs. Clinton," said Leslie Sanchez, who served in the George W. Bush administration but is not affiliated with any candidate. "There's nothing he could have done to overcome that national sentiment."
After Rubio attack, a return to wonkishness
Another pivotal moment came in October when Bush tried to attack Rubio on the debate stage for abandoning his day job and missing votes in the Senate to campaign. But the carefully planned attack -- which Bush had been telegraphing for days -- backfired when Rubio skillfully deflected, saying Bush never took issue with Sen. John McCain missing votes when he was running for president.
"The only reason you're doing it now is because we're running for the same position," Rubio said. "Someone has convinced you that attacking me is going to help you."
The awkward encounter was embarrassing for Bush and the governor failed to mount a counterpunch. One day later, Bush was already facing questions about whether his campaign was over.
"It's not on life support," he insisted, facing a massive scrum of reporters and cameras in Portsmouth, New Hampshire.
In the following months, Bush would lighten his attacks against Rubio, training his fire more on Trump instead. All the while, Bush kept a heavy commitment to rolling out policy plans nearly every week on a range of issues -- from entitlements to managing western public lands.
While Bush's wonkish side impressed voters at his town halls, it never broke through as a winning profile in an election year where bluster, bombast and soaring rhetoric was more appealing to an angry and frustrated electorate.
Bush regularly bristled at the idea that he needed to change stylistically or put on a "performance" at the all-important debates. But after the Rubio flap, his team hired a debate coach in November and tried to reset his campaign with a "Jeb Can Fix It" bus tour that zeroed in on his experience as governor. It coincided with the launch of his e-book, "Reply All," that used his emails to tell the story of what he calls his "servant leader's heart" when he was governor.
His stump speech became more compelling and he spoke with more alluring cadence. As he did before, Bush continued to woo voters at his town hall by his seeming ability to answer any question thrown his way. And he showed charm, compassion and accessibility as he took selfies and talked to any voter who wanted to meet him after his town halls.
"Every time he spoke at an event, he won hearts and minds," said David Oman, a senior adviser who worked on Bush's Iowa campaign. "I wish we could have had more."
South Carolina: One last family run
In New Hampshire and South Carolina, Bush dramatically shook up his stump speech and directly tried to take on Rubio and Cruz for being first-term senators, comparing them to then-Sen. Barack Obama in 2008 and calling them a "risky bet."
It appeared Bush was on the verge of a mild comeback after the New Hampshire primary where he placed fourth, ahead of Rubio. It gave Bush enough to keep him afloat heading into South Carolina, but it still wasn't the resounding victory he was hoping for.
When Bush landed in Hilton Head, South Carolina, the next morning after the primary, he was greeted to hundreds of voters in a retirement community in Bluffton, and a strategy to further embrace his family name kicked off immediately.
"South Carolina has been good to the Bushes in the past, and I'm hoping and praying it will be good again," he said. Indeed the state catapulted the 2000 presidential bid of his brother, George W. Bush, and handed George H.W. Bush a victory in 1988.
Bush told reporters that morning that the New Hampshire primary "pushed the pause button" on the race and erased Rubio's "coronation."
His campaign had two main strategies as he prepared to barnstorm the state of South Carolina: focus on the military and capitalize on the Bush name fanfare.
Graham, the state's senior senator and an expert on the military and foreign policy issues, campaigned for Bush at nearly every event in South Carolina the past 10 days, warming up the crowds with his Southern wit and playing the role of attack dog by lambasting Trump and Rubio.
The senator became so passionate that he grabbed the microphone from Bush again at the end of a town hall in Columbia last week to deliver yet another speech --- this time a fiery closing argument that angrily ripped into Trump for attacking Bush's brother in the most recent debate.
"I will never vote for a man who says that George W. Bush is a liar. You're not a Republican if you're asking Nancy Pelosi to impeach President Bush," he said. "Any man who says what Donald Trump said about George W. Bush is not a Republican worthy of your support. That's crazy talk."
For the first time, the campaign trotted out the 43rd President on the trail, where he headlined a rally with his brother in North Charleston on Monday. The event drew hundreds more voters than a normal Jeb Bush event, and it provided the campaign a full day of positive headlines. His brother offered veiled swipes at Bush's more dramatic opponents and tried to underwrite his brother's credentials to be commander-in-chief.
"Strength is not empty rhetoric. It is not bluster. It is not theatrics. Real strength, strength of purpose, comes from integrity and character. And in my experience, the strongest person usually isn't the loudest one in the room," the former President said to applause. "I've seen in my brother a quiet conviction and a core of conscience that cannot be shaken. And my hope is that the people of South Carolina will see this as well. This is a serious election for a serious job."
But two days later came a devastating blow. The state's popular governor, Nikki Haley, who Bush campaigned for in 2010 and helped advise her on policy, announced she was endorsing Rubio.
The news came just as Bush was about to hold yet another town hall in Summerville, one of 22 cities in South Carolina that the candidate publicly campaigned in during the past week and a half.
"I'm disappointed," Bush told reporters at the time, but still took the high road. "She's a very good governor and should I win the nomination there will be a role for her in the campaign, trust me, she's a great person."
The positive coverage quickly dwindled and poll numbers showed no noticeable improvement after George W. Bush's appearance. Bush's campaign continued with the family name strategy and brought former first lady Barbara Bush, 90, back on the campaign trail Thursday through Saturday. She helped generate buzz for her son in New Hampshire, and it was assumed she would be met with even more fanfare in South Carolina, where she attended high school at Ashley Hall in Charleston.
"He's done the most amazing things as governor. He's a great son. He's a great father. He's a great husband. He's a great friend. He's loyal," she said, while introducing her son at his final South Carolina town hall in the town of Central on Friday night. "And ladies and gentlemen, my boy, Jeb."
Also in attendance were his two brothers, Marvin and Neil, his wife Columba, and his son, Jeb, Jr., as well as a hoard of campaign staffers and volunteers -- some of whom appeared reflective in the wake of uncertainty surrounding Bush's campaign.
And in a moment that raised eyebrows, Bush thanked his audience at the end of his stump speech, saying, "Thank you very much for allowing us to close out our campaign here at your high school."
His staff quickly assured reporters he was only talking about his South Carolina campaign, but the quote nonetheless underscored a sense of finality that was previously lacking in Bush's rhetoric.
Yet it would only be 24 hours later when Bush would give his actual closing speech.
"I'm proud of the campaign that we have run to unify the country. And to advocate for conservative solutions that would give more Americans the opportunity to rise up and reach their God-given potential. But the people of Iowa, New Hampshire and South Carolina have spoken," he said. "I respect their decision."
After his brief speech, he shook hands with supporters for a few minutes before immediately leaving the hotel to go back to Miami with his wife, making some emotional goodbyes as he got in his car.