#Fail to the chief: When tech trips up presidential candidates

The run-up to the 2016 Presidential Election promises tech goofs, gaffes, and missteps galore. And we here at ITworld promise to keep track of them all!

Ronald Reagan laughing, but probably not over his badly timed joke about outlawing Russia

Politics and technology: An uneasy relationship

Thomas Jefferson was an inventor and Herbert Hoover was an engineer, but other presidents, candidates, and politicians have had a more, shall we say, fraught relationship with technology. Ronald Reagan, for instance, joked into a live microphone about "outlawing Russia forever" at the height of the Cold War in 1984. But with technology becoming an ever more important part of our daily lives, so too will some of the inevitable slew of political gaffes we'll encounter over the next 18 months of campaigning come in tech form. And we here at ITworld promise to keep track of them all! Here's a bunch to get you started; we'll update as more arise, and feel free to let us know if you read about one you think should be included.

Also on ITworld:

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REUTERS/Gretchen Ertl

Carly Fiorina's frowny face

Former HP CEO Carly Fiorina is touting her business acumen and tech savvy as a selling point as she begins her long-shot run for the Republican presidential nomination. But an unknown person with an axe to grind is seeking to undermine her on both points at once: launching along with Fiorina's presidential campaign was carlyfiorina.org, a site that featured 30,000 sad-face emoticons, one for each HP employee laid off during Fiorina's tenure. There's also a bonus page that name-checks Fiorina's legendary demon sheep ad from her failed Senate run.

Democratic presidential candidate Hillary Clinton delivers the keynote address at the 18th Annual David N. Dinkins Leadership and Public Policy Forum at Columbia University in New York April 29, 2015.
REUTERS/Brendan McDermid

Hillary Clinton's secret email server

Speaking as someone with his own custom domain name, I know it's cooler to have an email address that ends in a string you came up with rather than gmail.com or (shudder) aol.com. Still, 2016 Democratic front-runner Hillary Clinton should've maybe thought twice before using a private clintonemail.com address -- possibly run off a server in her Chappaqua home -- instead of one issued by the State Department while she was Secretary of State. There are a host of problems with record-keeping and transparency involved, of course, leading to calls for a subpoena of the server itself.

Former Governor Jeb Bush addresses the National Review Institute's 2015 Ideas Summit in Washington, April 30, 2015.
REUTERS/Jonathan Ernst

Jeb Bush takes email transparency a little too far

Hillary's scandal had barely erupted when a similar situation came to light from Jeb Bush's time as governor of Florida. He used jeb@jeb.org as his (public) email address throughout his tenure, but took the physical server out of the governor's mansion when his term ended and failed to release the emails as Florida's transparency laws required for seven years. When he did release them, they included some (nonclassified) national security material and the Social Security numbers of some Florida residents.

Republican presidential candidate U.S. Senator Ted Cruz speaks during the National Rifle Association's annual meeting in Nashville, Tennessee April 10, 2015.
REUTERS/Harrison McClary

Ted Cruz lets you see (too much) behind the scenes

Republican candidate Ted Cruz certainly embraced a low-tech vlogger aesthetic for his response to President Obama's 2015 State of the Union Address, recording a video message minutes later in the hallway of the Capitol building. Unfortunately, in their haste to get the message out, Cruz's staffers uploaded a video file that included a botched first take of the message; it was quickly taken down, but not before it was downloaded and preserved for posterity.

U.S. Senator Rand Paul, a 2016 Republican White House hopeful, speaks at a campaign event in Milford, New Hampshire April 8, 2015.
REUTERS/Joel Page

Rand Paul's opinionated tech staffer

A candidate's staff's political views aren't necessarily newsworthy, but when someone already a little Internet famous for her politics goes to work for a candidate, and her views are like that candidate's, but a little more extreme, well, you have the situation Rand Paul found himself in after hiring Marianne Copenhaver, a social media personality who calls herself "Libertarian Girl." Copenhaver, hired to do social media outreach (making her a somewhat public part of the campaign) and web design, holds strongly anti-war and anarcho-capitalist views common to many of Paul's followers. He's been trying to present himself as a more mainstream Republican, but has shown no inclination to dump Copenhaver over her opinions.

Former Republican U.S. presidential candidate Mitt Romney waits for the start of a welterweight bout between Manny Pacquiao of the Philippines and Juan Manuel Marquez of Mexico at the MGM Grand Garden Arena in Las Vegas, Nevada December 8, 2012.
REUTERS/Steve Marcus

Mitt Romney's killer whale

In 2012, Republicans were eager to reproduce the Obama campaign's tech-savvy get-out-the-vote push from four years earlier. Mitt Romney's staffers created Project Orca, a system that was supposed to coordinate the volunteers who would be making sure that Romney supporters were getting to polls. The day before the election, Romney staffers boasted of Orca's capabilities, but in the event the system was a disaster, causing mass confusion among the people it was supposed to coordinate. It probably didn't change the course of the election, but conservative-leaning Breitbart news quipped that Orca helped the Romney campaign "suppress its own vote".

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With Mitt app screenshot

Team Romney misplaces a letter

Earlier in his campaign, Romney tried his hand at creating viral social media memes with the With Mitt app, which overlaid Romney campaign slogans over photos you took with your smartphone. Unfortunately, the initial version of the app misspelled a crucial word in one of those slogans, offering the candidate's vision of "A Better Amercia." The error was quickly corrected and the campaign even tried to make lemons out of lemonade, buying a promoted tweet that appeared to those searching Twitter for the briefly popular #amercia hashtag.

Former U.S. House Speaker Newt Gingrich speaks during the inaugural Freedom Summit meeting for conservative speakers in Manchester, New Hampshire April 12, 2014.
REUTERS/Lucas Jackson

Newt Gingrich's dot com goof

Former House Speaker Newt Gingrich, who made an improbable run for the GOP nomination in 2012, has presented himself as a tech-savvy, forward-thinking futurist, garnering interest (and a certain amount of derision) when he proposed a moon base as part of his campaign. Unfortunately, Newt and his staffers weren't quite savvy enough to lock down the NewtGingrich.com domain, which was snapped up by a Democratic SuperPAC and set to redirect to various companies with embarrassing ties to Gingrich. (It wasn't the first tech slipup by Gingrich's team; in 2009, one of his lawyers threatened to sue someone for sending an @-reply to the politician on Twitter.)

The White House

The great computer vandalism that (probably) wasn't

When George W. Bush's team moved into the White House in early 2001, the first new inhabitants in eight years, word leaked out about a cheeky prank pulled by the departing Clinton staffers: some of the "W" keys had been removed from keyboards and stuck in random places. The first version of the rumor had it all being in good fun -- but then word got out that the Clintonistas had sliced computer and telephone wires and left "porn bombs" on the PCs. But the promised investigation into the cost of the antics was mysteriously silent, and then we all forgot it as more important things came along that year.

New York mayoral candidate Anthony Weiner attends a campaign event in the Rockaways section in the Queens borough of New York July 31, 2013.
REUTERS/Eric Thayer

The Internet never forgets your sexy messages

Political sex scandals are basically as old as politics itself; it's just the details that update with time. And we're deep enough into the computer age to really see the arc of change reflected in those sex scandals! For instance, in 2011, Congressman Anthony Weiner got in trouble for sending sexually suggestive pictures via Twitter, which seemed very cutting edge at the time; five years earlier, when Congressman Mark Foley got caught having sexually explicit AIM conversations with Congressional pages, that seemed kind of retro even then. We're very excited to see what the next political sex scandal technology might be (Oculus Rift?).

nixon tapes

Always getting into trouble

One of the ways the Internet made those sex scandals possible was that communication is recorded on central servers, not fleeting ephemerally like voices over a telephone wire. An earlier kind of recording technology got an earlier generation of politician in trouble. While the White House had had an audio recording system since FDR's presidency, that had to be consciously turned on; in 1971 a new system was installed that simply recorded when anyone started talking. The tapes recorded Nixon's participation in the coverup of the Watergate scandal -- and showed the power that tech had to make or break political careers.