Even by the normal laws of Republican political physics, 2016 was never a lock to be Jeb Bush’s year. The prospect that voters would pick three presidents from two generations of just one family always struck plenty of politicos as at least one Bush too far.

But the calamitous slow-motion collapse of a candidate so certain that his resume, Rolodex and fundraising prowess would make him a strong contender—if not the prohibitive front-runner—for his party’s nomination has nevertheless been stunning to behold. On Saturday evening, Bush dropped out of the presidential race after a disappointing finish in South Carolina, a state that had once been so kind to his father and brother.

In hindsight, there were telltale clues from the start. Bush’s Right to Rise super-PAC raised some $100 million last year—most of it before he even formally declared his candidacy—yet he still couldn’t manage to clear the raucous and splintered Republican field the way his older brother largely did in 1999.

As other campaigns scrambled to raise money, Bush’s PAC had money to burn, and burn it they did, mailing small video players with a 15-minute Jeb! documentary pre-downloaded to voters in New Hampshire, and buying digital billboard space in Iowa, where Bush wound up spending nearly $3,000 a vote and finishing in sixth place.

Bush’s message—a pledge of steady, sober, serious leadership, wrapped in a “kinder, gentler” tone—proved anathema in an angry age when executive experience and an equable temperament count as disqualifying attributes for presidential contenders in both parties. And to paraphrase Winston Churchill’s putdown of his rival Clement Atlee, Bush had “a lot to be modest about.”

Despite his longtime reputation as the smarter Bush brother, John Ellis Bush showed himself to have many fewer political I.Q. points than President George W. Bush ever had on his worst day—along with all too many of the diffident, distracted presentational deficits of their father on the stump. Paunchy or skinny, with glasses or without, Bush ran a joyless, self-conscious, disembodied campaign in which he always seemed to be looking at his watch, as his father so famously did in his 1992 town hall debate against Bill Clinton. The hortatory exclamation point at the end of his campaign logo only served to underline the oldest truth in politics from Jack Kennedy to Ronald Reagan: If you’ve got it, you don’t have to flaunt it.

Bush had his moments, chief among them a brave and principled argument that Donald Trump’s rampant anti-immigrant stance is not only bad policy but bad politics for his Republican Party, which needs Latino voters more than ever. Yet even a Google search of the phrase “Jeb Bush’s best moments,” yields mostly a litany of “Jeb’s Most Awkward, Dignity-Losing, Cringey Moments” as Talking Points Memo put it.

When a planned applause line—“We’re prepared to act in the national security interest of this country, to get back in the business of creating a more peaceful world”—fell flat, he asked an audience in New Hampshire to “please clap.” His intent was self-deprecation, but the impression he left was of defeat.

It’s hard not to summon at least a smidgen of sympathy for a candidate whose quaint credo was an appeal to a kind of decency in public life that has gone out of fashion. In 1994, when he lost the governorship of Florida that his family thought would be his, and his brother won the Texas governorship that once seemed unlikely, the first President Bush famously—and awkwardly—declared, “The joy is in Texas, but our hearts are in Florida.”

Four years later, on the morning of Jeb’s second, winning try at the job, the elder Bush so dreaded a possible encore that he confessed to his Secret Service agent, “I am one pathetic nervous wreck,” and told his old friend the journalist Hugh Sidey that he didn’t want to be with Jeb if he lost, “because it would hurt him even more to have us there.”

Unless he engages in public introspection atypical of his clan, we may never know what combination of sibling rivalry and public-spiritedness impelled Bush to embark upon a bruising, even humiliating, campaign that he would now surely not wish on even his own worst enemy. Whether the exercise, and its ashen result, should be a matter of pity or scorn is the eye of the beholder, of course.

Yet no epitaph for Bush’s effort could be simpler or truer than the words uttered by one of his longtime advisers on the eve of the New Hampshire primary. “We’re in striking distance in New Hampshire,” he told me with a bit of excessive optimism, before adding with dead-eyed aim: “But they’re not buying what we’re selling this year.”