The top ten worst modern presidential campaigns, ranked

The decline and fall of the Ron DeSantis campaign has led several people within the commentariat — which these days means anyone online with the ability to type a thought and hit send in even a semi-coherent way, despite lack of experience, background or the skill to even qualify as a volunteer — to weigh in on how awful, how terrible, how wasteful has been the DeSantis effort to run for the presidency. The effect is amusing, in part because it has led outright idiots to claim that if only DeSantis had refrained from criticizing Donald Trump at all, or if only he had criticized Donald Trump more, he would have succeeded.

Yet beyond the failure of analysis from the pro- and anti-Trump set, the well-in-evidence decline of the Floridian governor has also led to ahistorical claims that DeSantis’s campaign is one of the worst ever run, a catastrophic failure incomparable in the seas of time. On this score, analysts are revealing their bias toward the current and their inability to recall even the recent past. There are so many terrible presidential campaigns, so many that had the odds in their favor, scads of money and plenty of opportunity to succeed that far outpace the DeSantis effort, a corrective note is warranted. So, here is the list of the top ten worst presidential campaigns of the past fifty years — because ranking the performance or lack thereof of Miles Poindexter (judge, ambassador, senator and the man who rightfully accused Louis Brandeis of being a Red) on the presidential circuit would be a step too far.

10. Ted Kennedy, 1980

Kennedy’s challenge directed at Jimmy Carter was fomented and pushed by a portion of the Democratic Party that could not stand the Georgia peanut farmer president, and early polling had the Massachusetts senator besting the incumbent by double digits. But even with the resources, the family name and the backing of the Democratic Party elite, Kennedy drowned in his own hubris. His interview with Roger Mudd where he couldn’t answer a basic question about his desire to be president will live in infamy. As the late Jeffrey Hart noted at the time, in a single week Kennedy’s hopes “dissolve[d] like a snowman in early spring.” The best thing he got out of it was a speech about dreams never dying, which they very frequently do.

9. Kamala Harris, 2020

You forget how incredible her launch was — a massive turnout in her hometown of Oakland, an incredible script, a national future that was assured. She spoke to a bigger crowd than Barack Obama and seemed every bit like the next great thing in the Democratic Party. (This is the campaign that Ron DeSantis’s effort most resembles, other than the 2023 season of the Miami Dolphins. It’s really 1:1 — consider the boatracing of the hapless Denver Broncos equivalent to his 2022 November performance, and work forward from there, with the Tyreek Hill home fire as the resignation/firing of Jeff Roe.) Harris had a ton of backers, was viewed as the next generation of Democratic leadership and then got murdered on stage by Tulsi Gabbard in a debate that effectively ended her hopes of ever being the nominee. 

8. Rick Perry, 2012

From one debate meltdown to another, Perry had high hopes for his cowboy campaign, coming off an incredible primary destruction of Texas’s Kay Bailey Hutchison and equipped with populist messaging and polling showing him nipping at the heels of front-runner Mitt Romney. But even with the backing of a surging Tea Party donor base, Perry couldn’t survive a series of failures on the debate stage that positioned him as weak on immigration and light in his loafers on his agenda. Knifed for ideological infidelity on immigration and other issues by many of the same people who are now resolutely outside the Republican coalition — Bill Kristol, Jennifer Rubin, the Lincoln Project reprobates — Perry’s attempt to block Romney inevitability went nowhere. Oops.

7. Tim Pawlenty, 2012

It was on paper a timely, impressive effort that was absolutely suited for the Wall Street Journal editorial page and a Ross Douthat profile. A blue-state Republican governor who’d shown his effectiveness in midwestern leadership, TPaw had a brief surge of interest and a Michael Bay influenced ad campaign and a policy script written by Mitch Daniels (who wisely decided not to run, for our sins). He flamed out like every Vikings season except without the drama of ever coming close. This campaign lasted four months and wasted everyone’s time.

6. Scott Walker, 2016

Same thing all over again? Nope. Whereas the prior three efforts were all essentially challenges to the likely nominee, Walker was the one true front-runner for a long period leading up to 2016. He had proven his mettle in multiple elections in Wisconsin, became known as a fearsome opponent of government unions, and racked up all the right enemies. But when it came to transporting his message to the national stage, Walker utterly failed to connect — he was too nice, too simple, too much of a nerd. He raised a bunch of money but then canceled his campaign because it was spending too much. How very Wisconsin.

5. Phil Gramm, 1996

I love Phil Gramm, but he absolutely belongs on this list. A towering intellect, the Texan was known for his fiscal conservatism and his cornpone dialect, and raised a ton of money to challenge front-runner Bob Dole. But then he made the mistake of contending seriously in Louisiana, where his fortunes were beholden to a crew of miscreants who devoured his resources, decried his secular inclinations and went for Pat Buchanan instead. He ended up coming in fifth in Iowa, being denounced by James Dobson and making a lonely argument for free trade over protectionism in a doomed cycle for Republicans. The lesson is: never bet on Louisiana, they’ll just rob you blind.

4. John Glenn, 1984

Imagine the gift of 100 percent name ID, a reputation for courage and heroism, the total faith and confidence from the electorate that you can do anything paired with the accident of fate of being born in the swing state of Ohio. John Glenn had all these things, and also a literal movie about his astronomical heroism, and also the biggest war chest, and also the best poll numbers of any Democrat against incumbent Ronald Reagan. His campaign opened offices in nearly every state. He then proceeded to get absolutely trounced in Iowa and New Hampshire and withdrew without winning a single primary. He would spend more than a decade repaying his campaign debt.

3. Rudy Giuliani, 2008

Again, the 100 percent name ID — plus the incredible national popularity, a reputation for courage in the face of challenge, the pop culture humor, the definition of tough on crime, the status as America’s Mayor. Rudy Giuliani had all these things and more in his corner. Polling wise, he was the runaway favorite for the GOP nomination for more than a year. All he had to do was figure out the abortion issue and make peace with the social conservative skeptics, and the nomination was his. And then, Rudy forgot to run. He hung out in Florida, golfing and drinking and smiling for photos like a snowbird. Giuliani’s campaign, such as it existed, totally collapsed.

2. Hillary Rodham Clinton, 2008

You cannot have this list without HRC ’08. She raised a quarter of a billion dollars. She was without question the choice of every major Democrat — endorsed by twenty senators, she actually won more of the popular vote than Barack Obama. But this campaign, even with all its advantages, could not navigate the moment or figure out a way to present its candidate as a well-adjusted human person. Her best moment, presaging a political future where the Democratic Party would utterly ditch them, was downing a boilermaker in Indiana to show she could still party with blue-collar voters who stressed “Hussein” between her opponents’ names. This is the absolute worst campaign of the past fifty years, no question. Except…

1. Jeb Bush, 2016

Oof. Another quarter-billion-dollar effort, or close to it, and you still didn’t know how to answer a basic question about Iraq? And you spent that money largely to eradicate Marco Rubio? And you, arguably one of the most successful conservative governors in the modern era, ended your political career by becoming more known for your #JebNoFilter hoodie pic and “Please Clap”?

The thing is, you forget how popular Jeb Bush was before he became “Jeb!”. In the summer of 2015, he was earning 17 percent of the GOP vote when no one else was in double digits. And you have to admit this in your heart of hearts, he still would have been a good president. Guess what, America — he’s only seventy! That’s a spring chicken by Washington standards. Maybe he can try this whole thing one more time, perhaps with an extra exclamation point.