Jeb Bush had hoped to gain glowing headlines from the recent hiring of Ethan Czahor, a Southern California-based millennial who could help build him the Next Big Thing in political technology. But on Tuesday, Bush had to fire his political action committee’s new chief technology officer after reporters combing through the staffer’s online history found dozens of insensitive comments about women, gays and blacks.

Bush’s tech image took a second hit a few hours later when, he accidentally published online some Floridians’ Social Security numbers, email addresses and other personal information as part of a super-sized cache of 275,000 emails exchanged during his two terms in Tallahassee.


The former Florida governor — already challenged over campaign skills seen as rusty and not put to the test since 2002 — was forced to play defense after the online errors that could have been avoided with more advance preparation. His mistakes also served to resurrect questions over whether Republicans have a deep enough bench of digital and data talent to staff a dozen or more presidential primary campaigns and ultimately match up against what’s expected to be a Hillary Clinton tech juggernaut.

Add everything up, Democrats and some Republicans said, and the result is a candidate who is eager to look tech savvy but isn’t off to a very good start proving it.

“We’re seeing the result of the fact that the last time Bush ran for election, he had just gotten through Y2K, and Twitter was four years away from being created,” crowed Stu Trevelyan, CEO of the Democratic technology powerhouse NGP VAN.

“Dear reporters on ‘GOP digital surge’ beat: hiring this guy in the first place is clue to actual level of seriousness,” tweeted Joe Rospars, the 2012 Obama digital director.

Craig Stevens, a former spokesman for the administration of Bush’s brother, was more restrained but still critical: “These are just bumps along the road for Gov. Bush’s campaign. However, too many bumps can eventually ruin the ride. Campaigns will all go through staffing changes and make mistakes, but the larger issue here is Gov. Bush’s campaign’s rush to be the leader — and get out front — is leading to unforced errors. And when a campaign puts itself out front and steps into the spotlight even the smallest errors are going to be noticed.”

Jeb Bush’s aides maintain the two mistakes are unrelated and each comes with its own explanation: They weren’t ready to publicly unveil the CTO position and hadn’t yet done a full vetting of Czahor when a Time magazine reporter spotted the news on a LinkedIn profile. On the inadvertent disclosures, they say state officials are to blame for not scrubbing all of the sensitive data, which the Bush team then pasted onto its website. The Bush campaign is currently working to redact all the sensitive information.

“I wouldn’t underestimate him, but if people choose to underestimate what he’s going to do on the digital front they’re certainly free to do so,” said Justin Sayfie, a former Jeb Bush spokesman who noted that Bush had just published the first chapter of an e-book packed with 275,000 emails dating back to 1999. “It shows at a very personal level he’s been comfortable with technology, with email, probably before many elected officials were using it.”

Still, the two mistakes coming within hours of each other have opened Bush up to new waves of criticism that he’s out of touch with the rough and tumble world of modern, Web-based campaigning, where even the slightest delay responding to a bad turn in events can explode into a multiple-news cycle negative story. Democratic techies relished the two digital flubs landing in tandem. They said the hiring of the 31-year-old Czahor — who posted tweets between 2009 to 2011 referring to women as “sluts” and disparaging gays at his gym — demonstrates Republicans don’t have a deep enough bench of experienced tech to staff up a dozen or more presidential campaigns.

They said it is particularly noteworthy that Bush couldn’t hire the Republican National Committee’s top technology staffer Chuck DeFeo, a former George W. Bush 2004 online campaign manager, who instead just took a job with the Koch Brothers-funded data and analytical powerhouse i360.

“If this is the best guy they could find, it speaks to the marketplace of candidates willing to go work for a Republican presidential campaign and the policies it will inevitably represent,” said one senior Democratic techie.

“It also indicates the actual level of seriousness in the Bush organization about innovation and building a broad base of support, as opposed to just trying to lock up the establishment support and the megadonors,” the source added. “This is a big signal that it will be more of the same GOP we’ve seen for years. They spend a bunch of money to check the digital/tech box and get the press and their own big donors off their back, but they’re too addicted to the big money interests to do anything really different.”

Several Republicans interviewed Wednesday said they expect Bush to overcome his early tech mistakes. And while the GOP digital talent pool might be small, Bush will have little trouble filling his tech spots because of his high-dollar fundraising ability. Already, Bush’s PAC Right to Rise is getting tech help from Revolution Agency senior vice president Sheena Arora and Chris Georgia, who ran digital operations during the 2014 cycle for the National Republican Congressional Committee’s independent-expenditure arm. The PAC is no longer working with IMGE, an Alexandria, Virginia-based digital firm that originally built its website’s fundraising tools, according to a Bush aide.

Wesley Donehue, a South Carolina-based GOP digital operative with ties to another potential 2016 candidate, Sen. Marco Rubio (R-Fla.), said the Bush campaign’s experience with its CTO also demonstrates one of the challenges in hiring among a generation of tech experts who grew up on the Internet.

“The young techies that can take our party to the next level aren’t political operatives who have been trying to keep their noses clean,” said Donehue, CEO of Push Digital. “It’s going to be nearly impossible to build a talent pool when we put them under this much scrutiny. The world has changed and people are oversharing online. We have to recognize that trend, take the petty hits and keep pushing forward.”

As for Floridians’ sensitive information ending up in public, Donehue warned, “Digital marketing requires lightning fast speed. Issues are going to arise when you’re moving that fast. It happens on every single campaign.”

In a statement Tuesday, Bush spokeswoman Kristy Campbell distanced the former Florida governor from Czahor’s remarks, calling them “regrettable and insensitive.” On the personal information Bush released in emails, she said the former governor had asked state officials to first make redactions last May and that his PAC removed sensitive information in two emails that were flagged by reporters. Bush’s team is also doing its own internal review of the emails to find additional inappropriate disclosures.

On Twitter Monday, Czahor removed about 40 posts from his account, writing on the social network, “i deleted some old jokes i made years ago that i no longer find funny or appropriate. #learning #maturing.”

He also apologized in a pair of tweets on Tuesday connected to his resignation. “i only hope that my recent news won’t dissuade future techies from entering politics, regardless of political affiliations/backgrounds,” he wrote. “and i’ve resigned my role at right to rise. best of luck to everyone there, and i apologize in advance to whoever fills my position.”

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