"We need a president willing to challenge and disrupt the whole culture in our nation’s capital," Bush said during his announcement speech.
Turns out Republican voters certainly agreed with him on that point.
"I will be that president," he added.
On that point, he couldn't have been wronger.
But on June 15, 2015, he had good reason to believe he would head to the White House.
He was ahead in national polling. His closest competitor at that point was Wisconsin Gov. Scott Walker — remember him? Within a month, his super PAC's coffers would go on to total more than $100 million, a record-breaking sum. He had the support of the Republican donor class and much of the elected establishment (almost every elected Republican in Florida, past or present, would go on to endorse him). He had name recognition, and for a Republican, he was uniquely popular among Hispanic voters.
This was supposed to be his nomination to lose. Most candidates who start off in that position either find their campaigns felled due to controversy and scandal or in a bitter fight to the end with an insurgent candidate. It's often either a shameful exit or a second-place finish. Bush wouldn't get either.
The very next day, Donald Trump announced his candidacy.
The contrast between the two candidates couldn't have been deeper.
In Bush's speech, he talked lovingly of meeting his Mexican-born wife, Columba.
"In 1971, eight years before then-candidate Ronald Reagan said that we should stop thinking of our neighbors as foreigners, I was ahead of my time in cross-border outreach," he said of the courtship.
Bush would also praise America as "great and diverse."
Trump, famously, would declare in his announcement speech that "when Mexico sends its people, they’re not sending their best... They’re bringing drugs. They’re bringing crime. They’re rapists."
Bush promised an upbeat tone to his campaign.
"In any language, my message will be an optimistic one because I am certain that we can make the decades just ahead the greatest time ever to be alive in this world," Bush would say in his speech. "That chance, that hope, requires the best that is in us, and I will give it my all."
Trump promised no-nonsense takes.
"I watch the speeches of these people, and they say the sun will rise, the moon will set, all sorts of wonderful things will happen," Trump said of his competitor's speech. "And people are saying, 'What’s going on? I just want a job. Just get me a job. I don’t need the rhetoric. I want a job.'"
By July 20, Trump would overtake Bush as the Republican frontrunner. His position at the top would only be threatened, briefly, by Ben Carson.
Bush, meanwhile, soon slid to fifth place in the polls and would become Trump's favorite "low-energy" punching bag.
It was a sad, sad slump to defeat. Happy anniversary, Jeb!