Close to the check-in desks at WWDC 2013, we overheard a commotion. As delegates queued to pick up their show passes, one tall, dark-haired and rather scruffy-looking man was getting angry.

Event staff checked and checked again for a pass that wasn’t there, the man growing more and more agitated, his voice rising as his cheeks coloured.

And while you couldn’t make out his words from across the lobby, the body language was clear enough. He was still arguing as two burly security guards escorted him past the escalators and towards the front door, shouting over and over that somebody had made a big mistake. “Who was that guy?” someone just behind us asked.

We knew the answer to that one. That guy was John Appleseed.

Planting Appleseeds

If John Appleseed’s name doesn’t ring a bell, let us do some jangling for you. He’s the face you saw demoing the original iPhone, and in demos of subsequent iPhones, too. His face beamed out from the dashboard when Tim Cook showed off iOS in the car, and it’s his name you often see when Apple demos new software.

Appleseed’s connection with Apple goes back to the start of the 1980s. Apple then was a very different company than it is today: it became a public company in 1980 but wasn’t a buttoned-up, blue-suited corporation like IBM; it was a blue-jeaned, open-necked shirt, bearded kind of company out to make a difference. Apple was Steve Jobs’ and Steve Wozniak’s baby, but the firm’s CEO back then was Mike Markkula, who Jobs had lured out of retirement with the promise of Apple’s potential.

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Markkula wasn’t just a successful investor – he was a multi-millionaire by 32 – but a coder too, and he created some Apple II software under a pseudonym: John Appleseed. That didn’t go down well with the real, Cupertino-based John Appleseed, who had already created Apple II software under his own name. It wasn’t very good software, but Appleseed didn’t realise that. As far as he was concerned, someone at Apple was trying to pass themselves off as him.

Today he’d probably have hired a lawyer and filed suit against Apple, but back then there was a much easier way: confront Steve Jobs. Appleseed’s plan, if you can call it that, was simple: head over to Apple HQ in Bandley Drive and demand a meeting. But he hadn’t reckoned on Sherry Livingston, Jobs’ right hand.

Despite Appleseed’s best efforts, the door to Jobs’ office remained shut. If Appleseed’s first plan was ropey, plan B was even worse. He waited outside on the street for Jobs to emerge, apparently unaware that when Jobs left work, he did so on his beloved ’66 BMW motorbike. But Appleseed was lucky that day, because Jobs fancied a walk. Not only that, he was in a good mood: he didn’t tell Appleseed to get lost, and when Appleseed suggested that Apple could restore its karma by giving him a job, Jobs didn’t go ballistic. He just laughed. “Let’s walk,” Jobs said. It was to become the beginning of an unusual friendship.

John Appleseed didn’t get a job, but Jobs got his phone number – and every few months he’d call to arrange a meet-up. “It wasn’t a regular thing,” a source close to Appleseed told us. “They weren’t, like, beer buddies or anything like that. It was more… Johnny was like a sounding board for Steve, someone who wasn’t connected to Apple he could talk to and trust.”

It wasn’t an equal relationship, though. “I don’t think Steve particularly wanted to hear what John thought. I think Steve just wanted someone to listen to him.”

Thinking different

Jobs’ calls to Appleseed became more frequent in 1985 when his working relationship with Apple CEO John Sculley became a power struggle. “Steve was pretty paranoid back then,” our source recalls. “John was one of the few people he knew who didn’t have an agenda.”

Jobs’ career moves are well documented, but Appleseed’s are more sketchy: his jobs were mainly temporary – moving from firm to firm in Silicon Valley, unconcerned with carving out a particular career. He never did get that Apple job, but in the late 80s he made a second Apple connection: he met and began to date Kate Shannon, who worked in Apple’s accounting department. He and Kate were married in 1991 and they had a daughter, Jane, in 1993.

Jobs’ phone calls were less frequent in the early 90s: Jobs had a family and two companies – NeXT and Pixar – to run, and that didn’t leave much time for anything else. But by 1996 Jobs was back at Apple, and the phone calls resumed their previous frequency – and Appleseed would end up angry at Apple for a second time.

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Take a look at the TextEdit icon in OS X. If you blow it up or zoom in on the graphic to read the writing on the pad, you’ll see that it’s a note to Kate from John Appleseed. “Here’s to the crazy ones,” it says. “The misfits. The rebels. The troublemakers.”

“Everybody thinks Apple’s ad agency came up with the ‘crazy ones’ spiel,” an Apple insider told us. “But they didn’t. It was Appleseed’s idea, and Steve ran with it. The icon’s a nod to Appleseed, an inside joke.”

As our source tells it, the real story is this: Appleseed and Jobs were talking about Jobs’ personal philosophy, and the philosophies of Apple’s rivals. “You think different,” Appleseed told him. “You’re crazy enough to think you can change the world.” Maybe Jobs felt guilty for taking the credit, but shortly after the “Think Different” campaign began he sought Appleseed’s opinions more often, using him as a soundboard not just for Jobs’ ideas, but for actual products too. Appleseed may not have been an Apple employee, but he was an Apple insider.

The seeds are sown

At first, Appleseed was delighted. He got sneak peeks of new products. Jobs asked his opinion on pre-production hardware. Appleseed was one of the first to see the iPod, and the iPhone, and the iPad, Jobs convinced that Appleseed would stay silent – something that worried other Apple executives.

“Steve wouldn’t listen to them,” our source says. “To him, Appleseed was some kind of mascot, a lucky penny or something.” Our source compared him to the rapper, Flavor Flav. “You know how Flavor Flav doesn’t really do anything, but Chuck D likes having him around? Appleseed was like that.”

Appleseed wasn’t just Steve Jobs’ court jester, though. He became part of the marketing team – albeit without anybody telling him. Apple marketing materials don’t just appear overnight: they’re carefully planned and designed far in advance, and that means the marketing team needs photography and screenshots in advance, too. As far as Jobs was concerned, the fewer people who actually knew about unannounced products, the better – so why not get your real-world examples from someone that you already know and trust?

The first that Appleseed knew of his new role was at Macworld ’07, when Steve Jobs introduced the iPhone. “John nearly jumped out of his seat when he saw his face on the screen,” our source recalls. “Jobs hadn’t mentioned it to him. He’d just assumed it would be okay.” It wasn’t, because as part of the keynote Apple showed a video of the iPhone being activated – and that video showed Appleseed’s real mobile number (408-550-3542) and email address (appleseed_john@mac.com).

Inevitably, Apple fans tried to get in touch. “John was pretty pissed about that,” our source told us. “He had to change his number pretty much straight away.” Jobs apologised, but similar errors would plague Appleseed over the years: he had to take down his Facebook account after it was featured in an iPhoto demo, and at WWDC 2008 he was alarmed to see his name on the ‘fusion of CT and PET’ scan demoed by MIMVista.

“The actual scan wasn’t John,” our source says, “but he’d had his details leaked so many times that he just assumed that it was.” Appleseed put up with it, though. Irritations aside, he enjoyed being in the (infinite) loop, the feeling of being part of a remarkable business success story.

Out of the loop

Tim Cook didn’t share Steve Jobs’ high opinion of Appleseed, though, and when he became CEO, it was the beginning of the end. Jonathan Ive for one was relieved.

“Jony never understood why Steve liked having him around, so he was pleased when Tim cut the lines of communication,” our source says. “But Appleseed took it hard.” Appleseed took the excommunication very personally. It didn’t help that Apple had found a new family for its product demos: from late 2011, Apple marketing featured younger, prettier individuals such as Kevin Dolan, Katharine Johnson and Janielle Penner. “John started drinking,” a friend told us. “It became a real problem for him.”

Appleseed would call Apple HQ at strange hours, leaving long, rambling messages. On several occasions he turned up at Infinite Loop, clearly the worse for wear, and rumours swirled that his wife, Kate, had kicked him out of the house. It was surprising, therefore, to see his face at this year’s WWDC – not outside, trying to get in, but up on the big screen as Tim Cook demoed iOS In The Car.

“That was a real dick move,” the friend says. “The guy’s basically living in his car by this point, and they’re using his face to demo in-car entertainment. There’s no way that wasn’t deliberate.”

It’s clear that whatever the future holds for John Appleseed, he isn’t going to find it at Apple. “John was never part of the Apple family,” our source explains. “He was part of Steve’s family. And when Steve died…” Looking back on the keynotes now, the irony is obvious: while there’s endless footage showing Appleseed calling Apple, there’s no footage of anybody actually taking his calls.

The real Appleseed

The real Johnny Appleseed isn’t any relation to the fictitious one you see in Apple’s marketing materials and keynotes: the original Appleseed died in 1845. It wasn’t his real name, either: he was born John Chapman in 1774. Appleseed came later when he was a nurseryman, bringing non-native apple trees to parts of Indiana, Illinois, Ohio and Pennsylvania.

Chapman was an American folk hero, but unusually he didn’t have to wait until he was dead to become one; in 1830, when Chapman was very much alive, author Henry Howe collated many stories of his exploits. The stories paint Chapman as quite the role model: he was kind, lived humbly, cared for animals and preached the gospel as he travelled. He was a friend to Native Americans, cared about the environment and was more interested in helping others than amassing a personal fortune.

According to The Straight Dope, his attitudes were the opposite of other frontiersmen and women: “He thought it cruel to ride a horse, chop down a tree, or kill a rattlesnake.” The legend portrays Chapman as a dreamer, merrily scattering apple seeds as he strolled, but he was much more organised than that: Chapman created plant nurseries and returned regularly to check on them – and he planted the nurseries where he predicted settlers would one day come. When his predictions, ahem, bore fruit his trees were already several years old and ready to sell – and they sold because the apples they grew were perfect for making alcohol.

Like Steve Jobs, Chapman had charisma: as one lady told Harper’s New Monthly Magazine in 1871, “His was a strange eloquence at times, and he was undoubtedly a man of genius.” She was clearly rather taken with him, but then again, he wasn’t the kind of person you’d forget in a hurry: big-boned and sinewy, dressed in an old sack, wearing a tin pot on his head.

Chapman died in 1845, but his legend lives on in everything from Disney cartoons to NOFX records and the icon for Logic Pro X. Johnny Appleseed may be dead, but he certainly hasn’t been forgotten.

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