Once upon a time, eight Senior VPs formed Steve Jobs’ inner circle.

Steve empowered them because they were talented, strategic, trusted and in tune with his vision.

Well, time marches on. Apple doesn’t have Steve anymore. Tim Cook has reigned for nearly nine years. One by one, most of Steve’s Gang of Eight have been replaced.

Today only Tim Cook and COO Jeff Williams remain. The original Big Guns of hardware, software, retail, marketing, finance and legal have all checked out.

Apple and the art of the exit

Steve once said that hiring brilliant people was his most important job. For some inside Apple, saying goodbye to them is a critical job as well.

Say hello to Apple Media Relations.

To placate investors, this group crafts a story for every leadership departure. Its press releases are designed to minimize—or gloss over—potential negatives. In this sense, Apple is like every other monolithic company.

Consider the Phil Schiller sendoff.

The title of the Apple’s release almost makes it sound like Phil isn’t leaving, he’s simply moving to a higher plane of existence: Phil Schiller advances to Apple Fellow.

This puts Phil on the list with Wozniak and others who have no active role. Phil will be the exception, continuing to work on the App Store and Apple events. Or so they say.

I’m skeptical because there’s no penalty for telling tall tales. If a press release of this type ultimately proves false, no problem. By that time, we’ve all moved on.

Jony Ive is a good example. His departure was potentially devastating news, since he was Steve’s #1, and his contributions played a primary role in Apple’s rise to world dominance.

Cue the Apple storytellers. They told us Jony was leaving to start his own design firm, but have no fear—he’ll continue working on projects for Apple. More than a year later, not a peep.

Then there was the jettisoning of Scott Forstall, head of iOS Software. Scott was a primary Steve-mate going way back to NeXT. But alas, he was responsible for the Apple Maps fiasco and didn’t mix well with Jony.

According to the press release: “Scott Forstall will be leaving Apple next year and will serve as an advisor to CEO Tim Cook in the interim.” Yes. Of course.

But let’s get back to Phil.

How do we feel seeing him head for the door? Is the sky falling, or will the sun now shine a bit brighter?

Steve’s show partner

To Apple fans, Phil’s most visible role was serving as Steve’s sidekick at Apple product events. He was really good at it—entertaining in his own way, but never overshadowing The Boss.

The most vivid memory we have of Phil’s performing days was his onstage “death leap” designed to demonstrate the world’s first mainstream wireless laptop (iBook).

To many, Phil’s 20-foot leap was a literal confirmation of the duo’s relationship: “When Steve says jump, Phil says ‘how high?'”

That assessment, of course, is grossly unfair. The reality is that Phil was a trusted Steve advisor and confidante going back to the founder’s return in 1997.

Still, Phil’s influence was not without its dark side.

Schiller the chiller

During the Think different years, we at the ad agency had regular marketing meetings with Steve in the Apple boardroom.

Participants included the leaders in advertising, media, product design, packaging and strategy. Steve loved the cross-pollination and encouraged open discussion.

Over the years, we presented an endless stream of campaigns and ads—for TV print, outdoor and radio—many of which inspired debate.

Phil was not exactly a hero to the agency team.

He was a dubious judge of creative work, he didn’t have Steve’s level of taste, and he didn’t share Steve’s bravery, shying away from risky ideas.

Put another way, we were supremely thankful that Steve was the final arbiter of our work. He would routinely veto many of Phil’s suggestions.

Fortunately, despite his title, Phil was was never involved in ad development. He was present only when we showed finished work to Steve.

Absolutely, he had good thinking to share in our meetings. Steve trusted him for a reason. But he also contributed some highly questionable ideas, like “MacMan.” (Phil’s big naming idea for the computer that became iMac.)

It was my personal experience with Phil that caused a knot in my stomach when he became Apple’s chief marketer following Steve’s passing.

Under the non-marketer Tim Cook, Phil’s instincts would rule the day—and Steve could no longer stop Phil from being himself.

Flexing his muscles

Steve Jobs and ad agency chief Lee Clow had an unbreakable bond, going all the way back Apple’s earliest days.

Unfortunately, that relationship existed only at the highest level. Down in the engine room, there was often tension between Apple and its agency.

With Steve gone and Lee retired, the second tier on both sides took control—bringing those tensions to the surface.

Now sitting on the marketing throne, Phil changed the rules. He invited Apple creative teams to compete with agency teams for the big ideas. More ominously, he started building an in-house group that could supersede the agency.

Suddenly, the unthinkable was a distinct possibility. TBWA/Chiat/Day and its offshoot Media Arts Lab—long Steve Jobs’ most trusted marketing minds—could be cut out altogether.

Indeed, when internal emails between Phil and Tim Cook became public during the Samsung trial, the move to fire the agency was right there in black and white.

Ultimately there was no firing, but certainly the dynamics between Apple and its agency changed dramatically.

These were no longer the good old days, when Steve encouraged the agency to bring fresh ideas to the table, and to openly challenge his thinking.

Following the near-firing, the agency would have to be wary of the “last straw” forever hanging over the camel’s back. Not a great way to produce great creative work.

A humiliating start

Shortly after Phil took over the marketing reins, the 2012 Summer Olympics presented a big ad opportunity.

The result was the Apple Genius campaign. Honestly, I haven’t a clue who was responsible for this—the agency or Apple’s internal teams. But that hardly matters.

Hands-down, it was the worst campaign in Apple history.

This public embarrassment was relentlessly mocked for bad casting, bad acting, amateurish writing and its cringeworthy sit-com vibe.

It was a stunning example of the damage possible when someone without Steve’s level of taste takes over.

Given Apple’s history of great advertising, it was a dereliction of duty.

Sheepishly, Apple quickly removed all traces of the campaign from its website and YouTube. Within weeks, these three ads never existed.

Again, Apple PR sprang into action. This campaign was only designed for a brief Olympics run, they said. The cover story was as laughable as the campaign itself.

To a degree, things did improve in later years. Either Phil finally had a self-reckoning or someone else had it for him. In 2016, Apple hired Tor Myhren as VP Marketing Communications to lead Apple’s internal marketing group. Tor is a lifelong ad industry guy with qualifying credentials.

Whatever you think of Apple’s advertising since Tor took over is a personal judgment. At least there hasn’t been another Apple Genius moment.

By all appearances, Media Arts Lab’s job security has stabilized under Tor’s leadership, but—ya never know.

Phil’s “personal” decision

Whether or not Phil continues to play a role with Apple, he’s already proclaimed his “planned life change.” The final exit can’t be too far off.

His record is mixed, but we should tip our hats to a guy who gave 23 years to the Apple cause, starting when the company was on the verge of bankruptcy. His was an important role in Steve World.

That said, there’s nothing like fresh air. Companies like Apple thrive on recruiting and promoting new blood.

So once again, an Apple press release spins a highly suspect tale. Far more believable than Phil planning a life change is Apple planning a leadership change.

Whatever, the era of Phil is now behind us. As a result, Steve’s inner circle is almost entirely gone.

If you’re an optimist, this means that Apple will continue to be a hotbed of innovation, and it will continue to attract the world’s brightest designers, engineers and marketers far into the future.

It also means you’re perfectly suited to work in Apple Media Relations.