Matt Latimer is a former speechwriter for President George W. Bush. He is currently a co-partner in Javelin, a literary agency and communications firm based in Alexandria, and contributing editor at Politico Magazine.

I’m feeling bad for Jeb Bush. I’ve never been a supporter of a third Bush presidency—having endured the highs and lows of the second up close—but I can’t help but think about this coming Easter or Thanksgiving, or the next event when the whole Bush family is gathered around in one place.

The Bushes may come across as kindly, low-key aristocrats. But have no doubt: They are ruthless competitors. When I worked for President George W. Bush, he was racing Karl Rove to see who could read the most books in a calendar year. His father used to challenge people to games of horseshoes and speed golf. They are Trumpian in that way; winning matters in that family. A lot.


So how exactly does Jeb Bush look at a father who succeeded to the highest levels of power, whose approval is so obviously crucial to his psyche (“my dad is probably the most perfect man alive”), and not feel like he was the son who failed him?

How does he turn to George W., his perennially underestimated older brother—the so-called “dumb one”—who pulled off the same feat as their dad, and not feel the lesser man?

How does he cope with the fact that his failed campaign, for which his family’s hopes were so high, marked instead the end of their long dominance of the machinery of the Republican Party?

That all this anguish and more must surely be in play somewhere in the crevices of Jeb Bush’s keen mind—and will likely haunt him in some form or another over the next several years—is both cruel and unfair.

He was always the unluckiest Bush, always stuck in someone else’s moment.

He deserved more. Jeb was the one who stuck around while W. was off being “young and irresponsible.” Unlike some in the family, Jeb didn’t play at being a conservative. He didn’t mouth platitudes about his political philosophy to fit 30-second soundbites; he was the one who studied policy platforms and read thick tomes and the dry white papers put out by think tanks to understand why he believed what he believed. He was a good governor, a good citizen, a committed husband, a loving father, a devoted son. And a loyal brother (one of the qualities that haunted him this year as he struggled to explain his position on W’s invasion of Iraq).

Yet, time and again, the fickle tides of fortune rolled against him. The first instance, of course, was in 1994, when the two Bush sons both ran for governor, Jeb in Florida and W in Texas.

Jeb was expected to win his race; W expected to lose to the popular Ann Richards. But W was, as always, underestimated; Richards was, in response, overconfident. And she lost.

Jeb meanwhile found himself the earnest policy wonk challenging a more charismatic pol with a populist manner and a quick tongue—sound familiar? He lost by less than a percentage point in a year when the GOP won big everywhere else. W’s victory in Texas, in fact, allowed the prodigal son to claim the Bush mantle and start planning a presidential run of his own.

Of course, some of Jeb’s bad luck was his own making. He passed up perhaps his best chance to enter the White House—2012—when Republicans were hungry to defeat President Barack Obama and would have turned to anyone who might be able to get the job done.

“That was probably my time,” Jeb said later that year, after he opted out of the race. “There’s a window of opportunity, in life, and for all sorts of reasons.”

Instead, whatever the rationale—the coaxing of friends and advisers, the slick promises of SuperPAC boosters, a sense of duty to the family name—he chose to run for the presidency in the one election year that would never give him a chance. Thanks to his family name and his determination to enter the race at odds with the conservative base on key issues, he became harnessed to the many failures of a Washington in which he never actually served.

And there were more bad breaks—a meeting with Mitt Romney that led Romney to dub Jeb a likely loser. The decision of his young protégé, Marco Rubio, to challenge him for the affections of an identical base. The entry of John Kasich, who ran the hopeful, moderate campaign that Jeb had once promised.

Of all the times his Apple watch could have decided to go off, for apparently the first time in his life, it had to happen during a videotaped editorial board meeting, where he was made to look like a goofball.

And for some reason, someone on his staff handed him a hoodie without telling him how it worked and then videotaped his tortured efforts to wear it for all the world to see.

And of course the biggest stroke of bad luck was Donald Trump. For all of his faults, the New York businessman has the instinctive talent of getting into his opponent’s head. From their first encounter, he entered Jeb Bush’s brain and built a chain of golden hotels there.

After “yuge” embarrassments in Iowa and New Hampshire, Jeb turned to “Bush Country” in South Carolina and was snakebit again. First, he had the misfortune of being shackled to Sen. Lindsey Graham, who seems to have made a second career of being the official sidekick for the Old Guard.

Then, just a day after Jeb bragged about the critical importance of Gov. Nikki Haley’s endorsement, she stuck the shiv in him by endorsing his less experienced rival.

Even before his humiliation in South Carolina became official, it was leaked to the press that W. was “on deck” to give the hook to his little brother. Which made Jeb’s last few tortured days on the campaign trail even more painful and awkward.

I knew South Carolina was the end. It was not because of the polls. For me, it was all about his glasses.

On Jeb Bush, they made him look like the science teacher who told lame jokes and coached the high school quiz bowl team in his spare time. Everyone around him must have told him so. And yet he bravely donned them, proudly out of fashion, a defiant gesture against the modern political age. When they went—Jeb wore contacts for the first time in his life last week—it made things even sadder somehow. In a last gesture of futility, he had jettisoned the last thing that was still him.

Many, many pundits are in the process of dissecting the failures of the Bush campaign—the false-if-comfortable assumptions, the retro 1990s vibe, the ever-changing messages, and strategies, and excuses. I will leave that to them. My thoughts dwell on the candidate himself—a good and capable man—and what happens to him now that his exclamation point is neatly packed away.

There is one final irony. In the end the voters may be the unlucky ones. Earnest, thoughtful and modest, Jeb might well have been the best of the Bush presidents. If only he hadn’t been the third one.