TNR’s Rebecca Leber’s headline says it all: “Jeb Bush Is Having a Technologically Illiterate Week.” As noted here earlier this week, there was the email dump that unnecessarily exposed thousands of private emails and social security numbers from people who thought they were privately corresponding with the Governor of Florida. But that’s not all:

On Monday, he announced the hiring of Ethan Czahor as chief technology officer of his PAC, Right to Rise (Czahor resigned the next day).The campaign never scrubbed Czahor’s social media accounts before the announcement, and BuzzFeed quickly found the staffer’s misogynist tweets from 2009-2011. Czahor as called women “sluts,” tweeting that “most people don’t know that ‘halloween’ is German for ‘night that girls with low self-esteem dress like sluts’” and “new study confirms old belief: college female art major are sluts, science majors are also sluts but uglier.” It’s the kind of thing you’d expect a campaign would vet, and delete, well before announcing any hire, let alone a CTO (or perhaps not hire him in the first place?).

Leber thinks these signs of Bush’s lack of tech savvy could afflict his campaign as it has past GOP ventures:

Party leaders already know how a campaign’s poor grasp of technology can hurt them in elections. In 2012, Mitt Romney launched bug-filled smartphone apps for fundraising and campaigning. One was supposed to deliver data on election-day polls, but often gave false information and even crashed on election day. Romney’s slow rollout of new website and mobile features conceivably hurt his internet fundraising.

But I think Jeb has a bigger problem: there are signs his Big Economic Message was going to revolve around his supposed awareness of the technological revolution’s impact on how to conduct economic policy. An unintentionally funny post earlier this month from Ron Fournier showed Bush trying to explain all this to the pundit, impressing him mainly with the enthusiasm he showed which is often lacking in his formal speeches:

This is Bush at his wonky and provocative best. Removed from the stodgy theater of the Detroit Economic Club, the soon-to-be Republican presidential candidate recounts his visit Wednesday morning to a hip new manufacturing company, Shinola, and a business incubator called Detroit Creative Corridor Center.

At those stops, Bush saw the manifestation of his vision for post-industrial America—a time when 20th century institutions are completely disrupted and refitted; when the so-called shared economy gets folded into a tech-juiced new economy; and when government helps spur innovation, or gets out of the way.

This is all so 1990s, but it seemed to impress Fournier, who gets pretty animated at Jeb’s cool and hip understanding of this stuff:

If his brother, former President George W. Bush, was a compassionate conservative, Bush is trying to be a 21st-century conservative—a center-right leader who talks more about reforming government than shrinking it, even if the results are the same.

Bush tells me about Hernando de Soto Polar, the Peruvian economist who specializes in the so-called informal economy (removed from taxes and government oversight). The economist documented frustrations of entrepreneurs across the globe whose innovations are crushed by crony capitalism and government monopolies, including a Tunisian man who in 2013 set himself afire in protest. “We’re not Tunisia by any stretch of the imagination,” Bush says, but “we’re getting more and more complicated.”

“This should not be an ideological question,” Bush continues, before slipping into the clunky language of Peruvian economists and high-tech disrupters. “Transparencies about how we create rules around society have to be a part of the solution for people to be successful.”

Sure seems to me that Jeb’s had the same insight that Newt Gingrich had a while back: engaging in techno-babble is an excellent way for a reactionary politician to pour old wine into new bottles and make shilling for deregulated and untaxed capitalist enterprises sound cool. If that’s true, then yeah, it could be a big deal that he keeps showing he cannot find his butt with both hands when it comes to understanding reasonably simple phenomena like email and social media.

Ed Kilgore

Ed Kilgore is a political columnist for New York and managing editor at the Democratic Strategist website. He was a contributing writer at the Washington Monthly from January 2012 until November 2015, and was the principal contributor to the Political Animal blog.