Rick Perry, who dropped out of the 2016 presidential race on Friday, was always a long shot. It seemed hard to imagine that the erstwhile Texas governor could win the nomination in a field decidedly stronger than the one he failed to overcome in 2012. And in the end (which didn't come all that long after the beginning), what Perry hoped to be a redemption song turned into a swan song. Mistakes were made. The campaign gambled Perry would make it to the first "varsity" debate and that donors and supporters would believe again. He didn't and they didn't. (A necessary disclosure: My wife advised Perry's ill-fated campaign.)

There's no guarantee Perry would have risen to the occasion even if he had made the main debate stage. There may be little correlation between being a good debater and a good president, but there seems to be a strong one between being a good debater and being a good candidate.

Regardless, Perry never really got the chance. So we are left asking questions like "What if today's more prepared Rick Perry had run in 2012?" or "What if John Kasich hadn't gotten into the race and bumped Perry out of that last debate slot?"

The world will never know. Yesterday's rock stars are today's forgotten men. The political gods are fickle.

But here's one clear lesson of Perry's failed campaign: Texas swagger no longer travels well. Blame changing demographics in America, and George W. Bush.

In my forthcoming book Too Dumb to Fail, I document how several Republican presidents, including Gerald Ford, Ronald Reagan, and George W. Bush, all profited politically by feigning a sort of everyman ignorance. After losing a congressional bid, Dubya reportedly vowed that he'd never be "out-countried" again. This was smart short-term politics, but it also reinforced the notion that the GOP was the "stupid" party. That's a notion that haunts us, and Perry, to this day.

For a long time, though, being a "good ol' boy" was decidedly better than being an effete urbanite, and Republicans liked this contrast. Times are changing. Republicans are running out of old, white, married, rural voters. Being a "cowboy conservative" ain't what it used to be.

As I have long argued, conservatives should "modernize, not moderate." Some of this does include emphasizing substantive policy positions that might better appeal to 21st century Americans. But a good bit of it involves style.

Younger, more diverse, and cosmopolitan voters aren't so much embracing liberalism as they are rejecting what might be described as a caricature of a Republican. It's an image, largely of Republicans' own creation, that repels these voters culturally and aesthetically. A 2014 survey of millennials, for example, demonstrated that "[o]ften, they decided they were liberals because they really didn’t like conservatives."

The stereotypes that George W. Bush helped cement about the "dumb" swaggering cowboy made it almost impossible for Rick Perry to reinvent himself. The two men were never particularly close, but the prospect of electing another Texas governor (literally, the next Texas governor after Bush) was always going to be a tough sell, especially since the two were stylistically very similar. Bush left office extremely unpopular, and didn't just damage the Republican brand; he did specific damage to a particular type of Republican.

Consider the case of George Allen, who was thought of as a bit of a rock star as governor of Virginia and U.S. senator. Political insiders viewed him as the likely GOP nominee in 2008. But he fell apart, and I don't think it was just the "macaca" gaffe that did it. It was also the Confederate flag, the cowboy boots, and the "Welcome to America and the real world of Virginia" line. (People assumed he reserved that for the young man he called "macaca." In fact, this was his shtick. Allen said virtually the same thing to me the first time I met him and told him I was from Maryland).

It's hard enough to get a second chance to make a first impression, but it becomes doubly difficult when your persona viscerally reinforces urban America's pre-existing negative notions about Southerners. These biases and stereotypes may not be fair. But whoever said running for president would be? In the end, Perry's accent and swagger were too much a part of our collective conscience for even hipster glasses to overcome.