Chapter 16

Blind Spots, Grudges, and Sharp Elbows

A few weeks after the debut of the second iPhone, I got a call from John Nowland, the head engineer at Neil Young’s recording studio at his ranch near La Honda, California. John and Neil’s publicist and I had spoken for a year or so about possibly working on a Fortune profile about the rock star’s serious technological forays into audiophile-quality digital recording and biofuels for cars. Like me, Neil has a hearing disability, so during our initial meeting he and I spent some time comparing notes about what it’s like for a musical person to live with damaged ears.

Nowland told me that Neil wanted to send Steve a set of new, remastered vinyl editions of every album he had ever recorded. It was intended as a peace offering of sorts, and as a reminder of the peerless sound quality of old-style analog recorded music. Neil contends, with some justification, that the demonstrably inferior recorded sound quality of digital music, which was introduced with CDs, only got worse with the shift to compressed digital audio files. Half a decade earlier, shortly after the iPod hit the market, Neil had complained publicly about the fact that the digital format Apple used for the music sold on the iTunes Music Store compressed sound files so much as to render the music unbearably “compromised,” in his words.

Steve could be pretty thin-skinned when someone prominent criticized the aesthetics of his products. He took great umbrage that Neil would, as Steve put it, “pop off in public like that without coming to talk to us about his technical concerns first.” From that point on he had rebuffed all of Neil’s attempts to smoke the peace pipe.

Still, I knew that Steve enjoyed listening to records on vinyl from time to time, so I agreed to call him to see if he’d like to get the LPs. Steve answered the phone on the second ring, and I explained what I was calling about. We had talked about Neil’s criticisms a year or so before, and I thought this might soften his grudge.

Fat chance. “Fuck Neil Young,” he snapped, “and fuck his records. You keep them.” End of conversation.

Yes, Steve Jobs had grown and changed enormously over the course of his lifetime. If personal evolution is the long process of making more of our strengths and learning to moderate our weaknesses, Steve can be said to have succeeded brilliantly at the first, but not always so well at the latter. He had blind spots, grating behavioral habits, and a tendency to give in to emotional impulse that persisted his entire life. These characteristics are often used to make the case that Steve was an “asshole” or a “jerk,” or perhaps simply “binary”—that odd adjective often used to convey the sense that he was half asshole/half genius from birth to death. These aren’t useful, interesting, or enlightening descriptions. What’s more illuminating is to take a look at the specific ways in which Steve failed to do an effective job of tempering some of his weaknesses and antisocial traits, and to consider how, when, and why some of them continued to flare up even during the years of his greatest effectiveness as a leader.

DURING THE LAST decade of his life, the issue of Steve’s character would come up periodically. With all his heady success at Apple since the turn of the century, there seemed something incongruous about the occasional, stubborn persistence of certain problematic behaviors. They didn’t resonate with the image of Apple as a company all about creativity, potential, and the good that came to humanity when imaginative people used ingenious technological tools to amplify their own potential.

Apple’s cool, creative reputation wasn’t just a veneer, even though the company did work hard and masterfully to propagate that image with Lee Clow’s brilliant ad campaigns, Jony Ive’s minimalist designs, and Steve’s exacting product introductions, where music players and cellphones were associated with words like magical and phenomenal. It was also deserved and hard-earned, especially after the iPhone became the most popular consumer electronics device ever. Apple now was bigger and more influential than Sony had ever been. But Steve’s own actions could sometimes undermine the vision. How did that sleek, clean, and austere façade square with, for example, the moment in 2008 when Steve called Joe Nocera, the New York Times columnist who had once profiled him for Esquire, “a slime bucket who gets most of his facts wrong”? How could a company with Apple’s cherubic marketing glow make its devices in Foxconn factories where the drudgery and difficult working conditions resulted in more than a dozen assembly-line workers committing suicide? What about those deals encouraging book publishers to switch en masse to the agency model Apple preferred, where publishers set (and raised) ebook prices in a concerted effort to pressure Amazon to raise the prices it charged? What was the justification for the mutual under-the-table agreement with other Silicon Valley powerhouses not to hire one another’s engineering talent? And how “nice and cuddly” could a company or CEO be that let former top executives take the fall when the Securities and Exchange Commission took exception to the way the company doled out stock options worth hundreds of millions of dollars?

In some of these cases, the perceived moral transgressions were likely overstated, or failed to take into account all the circumstances. But Steve exacerbated many contentious situations with behavior that ranged from rude to insouciant to arrogant. Even for those of us who knew Steve well enough to have seen the significant mellowing in his personality over the years, his continued penchant for antisocial behavior was obvious, and a subject for debate. No one I have spoken to has a unified theory for the staying power of Steve’s childish behavior, not even Laurene. But it’s possible to understand the separate parts of Steve’s personality well enough to go deeper than simply characterizing him as wholly good, bad, or binary.

So when Steve spat his expletives about Neil Young, I just laughed. I wasn’t surprised. He could hold on to grudges for decades. Even after Steve had gotten what he wanted from Disney, Eisner remained a curse word to him. Gassée’s “sin” of telling Sculley that Jobs intended to oust him as CEO occurred way back in 1985; a quarter century later, Steve still snarled whenever the Frenchman’s name came up.

His grudges could even extend to companies that Steve believed had wronged Apple. His passionate antipathy for Adobe, for instance, was based in part on the fact that founder John Warnock had decided to also support Windows with his company’s software at a time when Apple was foundering. It was a perfectly rational decision at the time, when Macs held less than 5 percent of the personal computer market. But Steve saw it as a betrayal.

So when Steve himself was back on top of the world, he stuck it to Adobe by refusing to have the iPhone support a program called Flash. Flash was the leading software for viewing video and other interactive or animated content online. Adobe had done a good job with Flash, which was easy for developers to work with. But it had security holes, and could crash unexpectedly. Adobe had not been as diligent about correcting those problems as Steve would have liked. The iPhone was a brand-new networked-computing platform, and the last thing he wanted was to leave it vulnerable to hacking or security problems, especially in its infancy. So he left the program off the iPhone, and eventually off the iPad as well. Flash had been such a popular piece of software that Apple was deluged with complaints. But Steve was adamant, and in 2010 he issued a lengthy statement with six reasons he had not supported Flash. His reasoning was sound, but his words nonetheless smacked of revenge. Apple’s power was such that Adobe paid a price for its supposed betrayal. Flash survives, but Adobe has begun to focus more energy and investment on other streaming media technologies.

Steve’s biggest grudge of his later years was directed toward Google. There were many reasons for Steve to feel personally betrayed when Google introduced Android, the mobile operating system that mimicked many of the features of Apple’s own iOS, in 2008. What really galled him was that Eric Schmidt, Google’s CEO and chairman, had been a board member and a friend for years. Now his company was releasing an able, direct competitor to the product Apple had been working on intensely during Schmidt’s years on the board.

Even harder for Steve to accept was the fact that Google decided to make Android available to handset manufacturers for free, thus guaranteeing that phones made by Samsung, HTC, LG, and others could undercut Apple in the new marketplace it had created with their cheaper devices. Steve was downright livid. Google was pulling a page from the first chapter of Microsoft’s handbook for dominating the world. Clearly, Steve believed, Google’s intent in offering a free operating system was to propagate a standard across all cellphones and mobile devices, leading to nothing less than a replay of what Gates had done to Apple’s Macintosh with the release of Windows two decades before.

Determined not to let that happen again, Steve was not content to rely only on great products. In 2011, just months before he died, Apple unleashed a torrent of litigation seeking damages from Samsung, the leading maker of Android-based phones and tablets, and even asking for an injunction to prevent the Korean manufacturer from selling its phones in the United States. Steve didn’t sue Google directly, since the company was getting little direct financial benefit from Android, which was free. But he could go after the device manufacturers. (Apple also sued HTC and Motorola Mobility, a handset maker that Google bought in 2012.) He accused the companies of copying outright many of the key user-interface features of Apple’s iOS, launching a panoply of suits that were not settled until 2014. Apple won a major victory in U.S. courts, but the company still has not actually collected any money from Samsung. Meanwhile, both sides agreed to drop all Android-related lawsuits outside the United States in 2014. It seemed an acknowledgment that the litigation had become an albatross for all involved. Venting Steve’s anger against Google had cost the company at least $60 million in lawyers’ fees. Steve, whose intense focus was a huge competitive advantage, had created a massive legal effort that will likely prove, in the long run, to have been nothing but a distraction.

EVERYTHING ABOUT WORK was personal for Steve. Over the years, he had learned to trust this passion, and that trust had led him to intuitive leaps that had moved the whole industry forward. But the passion had a flip side, too.

For one thing, deriving so much of his own sense of personal identity from work meant that Steve, a man who could really dish it out, was surprisingly sensitive to criticism. Like most great public figures, Steve had fundamentally inured himself to the envious admonishments of others. But he did feel he deserved the occasional pat on the back for his contributions to modern life. More than once, after some of the tougher stories I wrote in Fortune criticized him personally, he emailed or called to say, “You hurt my feelings.” I had half expected him to be nonplussed, after some of those stories. But personally wounded? He didn’t always take the criticism so personally, however. When I wrote a column snarkily suggesting that the first version of Apple TV would make a great doorstop, and wondering if it might be of some actual use as a modernistic sushi tray, Steve emailed me as soon as he’d read it to say, “I can’t disagree with anything in this one.” He was the only CEO—with the possible exception of Gil Amelio—who ever reacted so personally to my coverage.

Steve brought an unguarded and painfully blunt version of his personality to his relationships at work. That helped him inspire a unique kind of loyalty that was the glue that held together the great teams that ran Apple with him. But his persona also presented a challenge when he had to make changes in the team, as he did a few times during his last decade. Steve would not indulge any laziness, entitlement, or overreaching ambition from members of his core team. He regularly pitted one against another in order to see whose ideas or intelligence would prevail. Everyone had to be in top form, solidly contributing and fully engaged, or they would find themselves subtly marginalized by Steve. His relationships with Avie Tevanian, Jon Rubinstein, Fred Anderson, and Tony Fadell, among others, demonstrated how quickly Steve could revoke the special insider status that was his to grant.

Anderson was the first to leave the executive team. He was ten years Steve’s senior and old enough to be the father of some of the newcomers. He’d had a great run as CFO and was widely recognized in the company as the man who had kept Apple alive long enough to bring Steve back. He had operated as one of the most autonomous members of the executive team, since Steve wasn’t expert in his field. There was symbolic significance in the fact that his office was just a couple of doors down from Steve’s. If the CEO wanted to make a big change to the budget, he’d just walk over and ask Fred to help him find the money. “Steve and I had a mutual, genuine respect for each other as business partners. It was genuine,” remembers Anderson. “So if he wants five million or ten million dollars more for this great idea or marketing program, he wouldn’t just haul off and do it. He’d walk down the hall and see me, and use his persuasive powers. ‘Fred, come on, can’t you find room for this?’ You know? That’s the way we worked.”

Fred had stayed on longer than he had intended, despite feeling a little weary. In fact, he’d thought he was ready to move on or retire as early as 2001. That year, Dell Computer had recruited him. Steve responded by convincing the board to make a onetime special award to Fred of options for one million shares, just to let him know how much he was appreciated. Steve also requested options grants of the same size for Avie, Ruby, and Tim Cook, and smaller amounts for other members of the executive team. It was a gesture that would come back to haunt Steve—and Anderson—but at the time it was welcome and enriching. Anderson stayed on three more years, despite the fact that Steve wouldn’t let him join the board of directors of any other companies. “Steve liked to control you. He liked to have you under his sphere of influence,” says Anderson. Eventually, Steve did let Fred join the boards of 3Com and eBay, and when Fred finally did retire, Steve asked him to join Apple’s own board.

When Fred’s retirement was announced in June 2004, Ed Woolard, the former Apple chairman, sent him a note thanking him for, among many other things, serving as “Chief Tantrum Controller of Steve.” At the last Top 100 meeting of Apple management that Fred attended as an employee, Steve broke down and cried during a video he showed in Fred’s honor. In his remarks at a going-away party at Cafe Macs, the company commissary, Steve reflected on the warmth everyone felt for Fred. Anderson still keeps two mementos from his retirement in his office at venture capital firm Elevation Partners: a plaque from Steve calling him “The World’s Greatest CFO” and a commissioned caricature portrait signed by all his closest coworkers, including Steve.

Jon Rubinstein and Avie Tevanian were the next members of the “Save Apple” team to depart. Ruby and Avie had been a buddy act of sorts, managing the hardware and software sides of Apple’s whole widget. Says Ruby, “There’s as much of the turnaround team’s DNA in Apple as there is of Steve’s, and you can still see it today.” They had been involved in every key decision at Apple since 1997. And before they left they helped pull off a move that they’d been talking about with Steve and with Tim Cook for years—switching the microprocessors that powered every Apple personal computer from the PowerPC chip to one made by Intel.

The primary buyers of the PowerPC chip were IBM and Apple. This was a customer base that paled next to Intel’s enormous market for Windows PCs and servers—millions of units a year for the PowerPC versus hundreds and hundreds of millions for Intel. Motorola could not match Intel’s manufacturing prowess. Intel reinvested much of the profit from selling all those processors into building more state-of-the-art manufacturing facilities (called “fabs”), which had come to cost in excess of $1 billion each. The bottom line was that switching to Intel held irresistible price and performance advantages, especially after Steve negotiated yet another sweetheart deal, this time with Intel CEO Paul Otellini.

The whole executive team at Apple anticipated that the switch would be difficult. For starters, the change would infuriate some customers, because users who wanted the latest and greatest software would eventually be forced to replace their older iMacs, PowerMacs, MacBooks, and PowerBooks. Second, Avie and his team had to make sure there would be no software glitches, so that buyers of the new Intel-powered Macs would be able to use the OS X–ready software they’d purchased for their older machines. Despite all that, the move was far smoother than anyone had anticipated. Since Avie’s team had ported the NeXT operating system to run on Intel-based systems years and years earlier, they were very familiar with the strengths and idiosyncrasies of the Intel’s microprocessors. The first Apple machines switched over in February 2006. The rest made the transition by that summer. The operation came off without any noticeable glitches.

This was the kind of technological excellence Avie and Ruby had helped ensure throughout their time at Apple. Nevertheless, neither one could see an interesting career path forward there, especially now that the iPod and other mobile devices had become Apple’s growth engines. Steve saw Avie and Ruby as, first and foremost, “old-time” computer guys. Tony Fadell and Scott Forstall were early members of the post-PC generation, and seemed destined to be the key leaders of the iPhone hardware and software efforts. The wheel was turning for Avie and Ruby, just as it had for Fred.

“Steve kept people in a box,” says Avie. Tevanian had talked to his boss several times about his itch to do something new, and in 2003, Steve had moved him into a role as the company’s “chief software technology officer.” It was unquestionably a promotion, but it turned out to be a job without much of a portfolio. Tevanian found himself with little concrete responsibility. He felt out of the loop, and realized that his new role would not work. “Being a pseudo individual staff person working for Steve doesn’t work, because he already has all the answers. He didn’t like it when I would be in a meeting where he was reviewing a product, and I would have an opinion. He just didn’t like it. And he grew to not like that I could be a senior person like that without having day-to-day responsibilities to deliver something,” he says.

Tim Cook, now Apple’s CEO, says that he worried about Tevanian leaving, and urged Steve in 2004 to figure out another challenge to keep the brilliant software engineer at Apple. “Steve looked at me,” Cook remembers, “and goes, ‘I agree he’s really smart. But he’s decided he doesn’t want to work. I’ve never found in my whole life that you could convince someone who doesn’t want to work hard to work hard.’ ” Another time, shortly after Steve had learned that Tevanian had taken up golf, Steve carped to Cook that something was really amiss. “Golf?!” he thundered incredulously. “Who has time for golf?”

Rubinstein, meanwhile, noticed that he too was getting less and less attention after Steve returned from his cancer operation in 2004. “In the beginning at Apple, it was a pleasure because we were all really in it together. I mean, it was really a team, we were partners,” he says. “But once Apple started getting really successful, Steve moved himself to the next level and started separating himself from all of us. It started to become all about him versus about the team. Over time it changed, where you were much less working with Steve and much more working for Steve.”

Ruby saw himself as CEO material, and envied Cook’s growing role. He also had started clashing with Ive, who had once reported to him but now reported directly to Steve. And he couldn’t stand Tony Fadell, the lead engineer for the iPod. Ruby and Fadell would resent one another for years, long after they’d each left Apple, each claiming responsibility for the iPod’s success, and each demeaning the other’s contribution. (Some wags took to calling Fadell “Tony Baloney.”)

Finally, it all got to be too much. Ruby says he went in to Steve’s office one day and told him he was tired, that he was ready to quit and go build his dream house in Mexico. He left on March 14, 2006—just a few weeks before Avie’s own departure. “It was a great experience,” Ruby says. “I wouldn’t have traded it for anything. It was wonderful in so many dimensions. I mean, it changed my life in so many different ways and I learned a lot from Steve. Steve could be a real jerk, no question about it, but I feel very warmly about him. I really do.”

Steve had considered himself friends with both men. But that personal level of involvement made their departures personally fraught. Every personable executive must confront this problem, but it was especially tough for Steve. While he had changed over the years, he still didn’t have a natural soft touch when it came to discussing career options with his closest colleagues. So things ended badly with both Avie and Ruby. Steve’s relationship with Avie, who had organized his bachelor party back in 1991, just petered out. His relationship with Ruby, on the other hand, ended with a bang.

Ruby built his dream house after leaving, but he was still ambitious. In late 2007 he was hired by Palm Computing, which remained a significant player in the handheld market. Ruby sent Steve an email to give him a heads-up that he was heading to Palm. Steve called him back about four seconds later, according to Ruby, and started saying things that left him flabbergasted. “He couldn’t understand,” Rubinstein remembers. “He said, ‘You’ve got plenty of money, why are you going to Palm?’ I’m like, ‘Steve, what are you talking about? I mean, you’ve got orders of magnitude more money than I have and you’re asking me? Are you joking?’ ”

To Steve, Ruby’s move was akin to treason. By taking another job, at an ostensible competitor to Apple, Ruby had, “failed the loyalty test,” to cite the words of Susan Barnes.

Ruby tried to reason with Steve, even suggesting that Apple and Palm “didn’t necessarily have to compete.” That wasn’t realistic, of course, given the clear faceoff between Palm’s handheld devices and the iPhone. In fact, it may have been just wishful thinking. In the end, it didn’t really matter. Palm fizzled out, unable to compete with the iPhone either on its own or as a division within Hewlett-Packard, which bought the company but closed it shortly thereafter. Ruby and Steve never spoke again.

Steve had made an effort to keep Ruby and Avie on board. But the fact that the new jobs he promoted them into turned out to be hollow is an indication of the ambivalence he felt about keeping them. In one critical way, Steve hadn’t changed much. He put the needs of the company ahead of any work relationship. He became even more pragmatic about this kind of thing during his later years. In important ways, his assessment of the team—measured by the same high standards he applied to himself—was clear-headed and brilliant. Losing employees, colleagues, and personal friends was hard on a personal level, for Steve and for everyone else involved in the transitions. But Steve had always believed that when the time came for a change in personnel, a company should move on as quickly as possible. It will soon find that circumstances change, and that it can do just fine without the old heroes.

Where Steve failed in these transitions is in the aftermath. His personal dismissal of Ruby, with whom he’d worked for sixteen years, was characteristic. When others could no longer match his level of effort and intensity, when they became less important to his plans for Apple, or when they left the company, Steve would lose interest. Steve cared more about the potential buying power of his customers than he cared about propping up departing veterans whose contributions he deemed waning. Avie or Ruby should never have expected anything different. Steve had treated his Apple cofounder, Woz, this way, and others along the way had been dismissed in similar fashion. He prioritized ruthlessly, and when Avie and Ruby tumbled down in the ranks of people who could deliver what he believed Apple needed, he moved on.

TWO MONTHS AFTER Avie and Ruby retired, Apple made a seemingly innocuous announcement, in which it tersely acknowledged that Nancy Heinen, the company’s general counsel—and one of just two women on Steve’s executive team—had quietly resigned. She was only forty-eight years old at the time of her “retirement,” yet the news made barely a ripple. One month later, however, the plot thickened when another Apple press release noted that the company had embarked on an “internal investigation,” at the behest of the Securities and Exchange Commission, into apparent “irregularities” in stock option grants made to senior management between 1997 and 2001. Nearly a year later, on April 24, 2007, Heinen would be formally charged by the SEC of being complicit in improperly managing the “backdating” of two 2001 stock grants: one of 7.5 million options to Jobs, and another—the one Jobs himself had initiated after Fred Anderson was recruited by Dell—of 4.8 million options to other members of the executive team. By backdating the options, Heinen had given Steve and his team better strike prices. That in and of itself wasn’t illegal—what crossed the line, however, was how the records accounting for the options were doctored, allegedly at Heinen’s direction, in a way that made Apple’s earnings report look slightly better than it was at the time. Eventually, Heinen settled with the SEC without admitting any wrongdoing, after paying a $200,000 fine and returning $1.575 million of proceeds from options she received from the grants in question.

Anderson had been chief financial officer at the time of the alleged backdating, and the SEC produced an email in which he cursorily approved Heinen’s suggestion of a specific strike date for backdating the options. He too was implicated by the SEC, for supposedly not paying proper attention to the grants, and settled the charges after paying $3.65 million of proceeds derived in the same way as Heinen’s.

All kinds of mitigating factors complicate the backdating story. Apple’s outside counsel, Palo Alto–based Wilson Sonsini Goodrich, had advised Heinen that backdating was probably legal; much the same advice it gave to several other tech companies who were eventually pursued by the SEC, including Pixar. Steve had authorized the backdating, albeit with the assumption that it was legal. And he did himself no favors with his testimony to the SEC. Explaining his own 7.5 million options grant, Steve sounded self-pitying. “It wasn’t so much about the money,” he said. “Everybody likes to be recognized by his peers.” He had hoped, he explained, that the board would come forward on its own with an offer of new options, given his success and the fact that a previous grant was underwater. “It would have made me feel better,” he told investigators.

Talk about tone-deaf. Even allowing for the fact that Steve was not feeling well on the day of his testimony, and that he never imagined his testimony would become public, his words accurately, if unintentionally, reflected a certain callousness that he applied to Anderson and Heinen’s plight. Anderson had resigned from Apple’s board about six months before the SEC came to its decision, when it became clear that the company’s internal investigation would lay the blame for the trouble at his feet, and at Heinen’s. Meanwhile, Steve himself was left untouched by the SEC. “I was hurt,” says Anderson, “because I have tried to live my life as a Boy Scout. The most important things to me are my set of values and how I conduct myself, you know? And everybody that knows me, whether at Apple or anywhere else, will tell you that I have incredibly high ethical standards and that I would never, ever knowingly do anything wrong. I mean, even with people. I always treated people with respect and protected a lot of people from Steve’s idiosyncrasies.”

Anderson deserved better treatment than he got from Steve and from Apple. (Heinen has not spoken publicly about her departure.) But by the time the backdating scandal became a public matter, he was no longer CFO, making him less important to Steve than he had been. Steve could be tremendously helpful to friends and colleagues in times of need, especially when they or their families needed medical treatment. He could also be cold and insensitive to coworkers when their personal issues obstructed what he saw as the company’s mission, or distracted them from giving Apple their full attention. With a little more empathy, and a little more caring for those who weren’t critical to his cause, Steve could have saved himself, and Apple, from a handful of unnecessary headaches.

FOR THE REST of his time at Apple, Steve would manage the company with a mix of old-timers and newcomers. Cook and Ive had been with him for years by now, as had communications chief Katie Cotton, and Phil Schiller, the good-natured head of marketing. Sina Tamaddon and Eddy Cue had gradually become part of the core, and Steve promoted Fadell to head up the hardware side of the iPhone project, and Forstall, another former NeXT whiz, to handle the software. Forstall and Fadell could have become the next “Avie and Ruby,” had they not viewed each other as rivals from the very start. They would clash and undercut each other even more than Fadell had banged heads with Ive and Ruby. Steve found himself refereeing disputes that were beginning to threaten the vaunted synergy that had always been Apple’s “secret sauce”—the blending of clever hardware and ingenious software into a single, magical digital widget. In fact, Fadell was such an explosive force that he would leave the company in 2009, and head off to form a new company, called Nest Labs, which makes a thermostat and a smoke detector that work with your home Wi-Fi network. Fadell is not remembered fondly in the Apple executive boardroom. When certain Apple higher-ups speak of him now, they sneer at the designer of “that little thermostat.” The definition of little is relative, of course. In 2014, Google paid $3.2 billion to acquire Fadell’s Nest Labs.

In the last years of his life, two avoidable controversies distracted Jobs from what he really wanted to be doing: working with this group on great new products. The two events played out, even after his death, in ways that made Apple, and Steve, seem arrogant, willful, and above the law. Starting in the mid-2000s, Steve was the informal leader of a group of Silicon Valley CEOs who agreed not to poach senior employees from one another. In 2010, the Justice Department filed a complaint in 2010 against Apple, along with Adobe, Google, Intel, Intuit, and Pixar, alleging that the companies had entered a series of agreements, recorded formally and informally, to not hire from one another. A class-action lawsuit followed in 2011, filed by an engineer at Lucasfilm on behalf of 64,000 employees of these companies, and others in Silicon Valley. (This lawsuit added Lucasfilm, which like Pixar is now owned by Disney, to the list of companies.) The plaintiffs alleged that the anticompetitive scheme cost workers billions of dollars in unrealized wage gains they might have enjoyed with unrestricted job mobility.

Emails subpoenaed during the investigation show that Steve was clearly involved. They also show him taking mordant pleasure at the fact that a Google recruiter was fired for poaching an Apple employee, after Steve had complained to Eric Schmidt, who was then CEO of the giant search engine company. When Jobs heard the news, his email reply was a smiley-face icon. Steve was hardly the only CEO to be caught with incriminating emails, but he was the only one shown making light of the personal impact of the collusion. Other chief executives seemed motivated primarily by a desire to not piss off Steve, who had become the most powerful employer in the technology business.

Tim Cook doesn’t see anything egregious in Steve’s thinking—even though he has since tried to settle the lawsuit by offering to pay hundreds of million of dollars to participants in the class-action suit. “I know where Steve’s head was,” he says. “He wasn’t doing anything to hold down salaries. It never came up. He had a simple objective. If we were working together on something—like with Intel, where we threw everything in the middle of the table and said let’s convert the Mac to the Intel processor—well, when we did that we didn’t want them poaching our employees that they were meeting, and they didn’t want us poaching theirs. Doesn’t it make sense that you wouldn’t, that it’s an okay thing? I don’t think for a minute he thought he was doing anything bad, and I don’t think he was thinking about saving any money. He was just very protective of his employees.” It’s a rational argument, insofar as it goes. All CEOs want to keep their best employees at their company. But it ignores the simple fact that making such an agreement with other companies, explicitly or otherwise, is illegal, according to the U.S. government and most antitrust lawyers. Steve, apparently, couldn’t be bothered even with acknowledging those rules.

That same attitude hurt Apple in another case it had to settle, in which the government alleged that Apple conspired with book publishers to raise the price of ebooks. As Steve prepared to launch the iPad, he was sure that reading books on the device would be seen as an attractive feature, one that he hoped would create profits for Apple while stealing customers from Amazon. He and Eddy Cue strongly encouraged book publishers to adopt the agency model Apple used on its app and iTunes stores—publishers could set the price of their ebooks, as long as Apple got 30 percent of the sale. Furthermore, they wouldn’t allow their titles to be sold at lower prices elsewhere. In this scenario, prices of ebooks would have risen uniformly from the low, $9.99 price Amazon often charged for new releases. The publishers would have enjoyed smaller profits but would have been able to set higher prices and avoid permitting Amazon to drive book prices down. Here, too, Steve’s emails did nothing to help Apple. His aggressive negotiating notes show that he was fully aware of the impact of getting all the publishers on the same page. Writing to James Murdoch, the son of News Corp CEO Rupert Murdoch, Jobs said that News Corp’s best option, he believed, was to “Throw in with Apple, and see if we can all make a go of this to create a real mainstream ebooks market at $12.99 and $14.99.”

It’s possible that Steve really didn’t see anything wrong with trying to build solidarity among publishers, because he had done the same thing with record company executives when setting up the iTunes Music Store. Nobody accused him of collusion then, even though he had insisted on setting a price of 99 cents a track. It’s also possible that a variety of assorted corporate safeguards—better legal counsel, better compliance efforts, and so on—could have kept Apple on the right side of the law in both the ebooks case and the labor collusion. But Steve had molded Apple into a tool for turning what unfolded in his imagination into real products, not an organization that conservatively guarded against the downside of his impulses. So the safeguards that did exist weren’t powerful enough to prevent the troubles that arose.

“Steve created a management approach that worked for the type of product that he had been thinking about,” Bill Gates told me after Steve’s death. “You know, if you were going to do hardware and software together, and you’re going to do a few super, super nice designs, and you’re going to do it end-to-end where partnerships aren’t the key thing, where you control that experience totally. He managed a great organization that was purpose-fit to that.” We had been chatting about why so many books had been written promising to reveal how to do business “the Apple way,” or “the Steve Jobs way.” Bill was describing why Steve is a unique managerial case, someone whose model has limited applications. “Maybe you should call your book Don’t Try This at Home,” he said, only half joking. “So many of the people who want to be like Steve have the asshole side down. What they’re missing is the genius part.” One downside to the Steve Jobs way of running a company, he opined, is that “This is not an organization with checks and controls.”

ALL HIS LIFE, Steve had tried to control the narrative about Apple by being the sole employee to tell its story to the public. There was a cost to this choice that didn’t really become apparent until the last years of Steve’s life, when his notoriety and Apple’s success drew attention to Cupertino as never before. Apple became the lightning rod for everything from criticism of the tech industry’s sustainability problems to corporate governance controversies that affected many other companies as well. And its spokesman was a mortally unhealthy man with a desperate impatience to deal with things that really mattered to him, not this broad array of nagging distractions.

Ever since getting sick in 2004, Steve had kept goals in his head of things he wanted to be alive for. Some were personal, like the school graduations of his kids. Some were corporate, like his desire to live long enough to introduce the iPad tablet computer. Dealing with the media circus that erupted in 2010 when a technology blog came into possession of an iPhone 4 prototype that a young Apple engineer left in a bar was nowhere on Steve’s list. Nor was flying back from a Hawaii vacation to manage an uproar that became known as “Antennagate,” the result of the discovery that the iPhone 4, if held at certain angles, would drop calls more frequently than past iPhones. And he had only passing sensitivity to corporate governance issues. Yet all these incidents, and more, added to the already immense task he faced of managing a sprawling international company with nearly fifty thousand employees during these years when he was quite truly dying.

It is part of the CEO’s job description to manage such distractions, and Steve was not particularly good at this even when he was healthy. He had always been impatient. But the cancer was exhausting him and bringing the kind of wearing pain he had never before experienced. Not surprisingly, Steve bollixed up things that he might have handled with ease under different, healthier circumstances.

For instance, reasonable people can disagree on the subject of whether Steve had a fiduciary responsibility to disclose his cancer earlier than he did, and to then keep the public informed of its progress. Steve felt, and perhaps naively wished, that this was a private matter, and so he skirted the truth about his disease again and again. But calling Nocera a “slime bucket” when the Times columnist called to address the issue did little for the reputation of Apple or its CEO. Similarly, Steve’s public comments about Apple’s response to the controversy that was set off when a spate of suicides occurred at the Chinese campuses of Foxconn, its leading assembler of iPhones, did more to hurt Apple than help it, in a situation where its record was actually fairly good for a big global corporation.

As Apple built up a supply chain that delivered more and more iPhones, iPods, iTouches, Nanos, and the like, it annually audited working conditions at the factories of its suppliers, and even of its suppliers’ subcontractors. But problems slipped past these audits. That’s not unusual; not surprisingly, the conditions of Asian manufacturing plants have been worrisome for decades. That’s unlikely to change. In a system set up purely to secure the lowest costs for U.S. and European manufacturers, workers are unlikely to be paid or treated particularly well. When Apple learned of the suicides, it actually responded quickly, pulling together a noteworthy task force to investigate Fox-conn’s factories, and taking other actions that some observers have deemed forward-looking. Again, reasonable people can disagree about the quality of Apple’s response. But what everyone can agree on is that Steve didn’t help matters with some of his public responses to the crisis, including the moment at a tech conference when he said, “Oh, we’re all over this one.” He sounded glib, in the way of any corporate CEO trying to smooth over an inconvenient truth.

Steve had come a long way in moderating some of the behaviors that had made the young man at the Garden of Allah such a volatile, difficult presence. Some of his old foibles hung on with persistence. Others had been tamed. And at the moment when the pressures of his job would have benefited most from his evolution, his illness added to the complexity of his task.

Heroic narratives aren’t supposed to have chapters like this. In the typical Pixar movie, or in the Disney animations that started getting better and better toward the end of Steve’s life, true emotions are unfrozen, reconciliations are wholly achieved. But Steve’s life wasn’t a movie. It was inspiring, confounding, and unabashedly human, to the very end.