Apple's 11 Biggest Failures

Apple sets the standard -- for both success and failure. Here's a look at 11 major screwups, some of which almost derailed the company

Rotten Apple: Apple’s 11 biggest failures

Rotten Apple: Apple’s 11 biggest failures

Apple has developed a reputation over the years almost on the level of religious faith: If Apple builds it, it will be a success.

Mac OS X, the iPod, iTunes, the iPhone, the iPad -- more often than not, Apple sets the standard, but its successes don't cover the whole story. The company’s periodic failings of arrogance, internecine warfare, and myopia have also played a key role in the company's storied history.

Here, in chronological order, are Apple’s 11 worst failures to date.

1. Apple Lisa (1983-1985)
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1. Apple Lisa (1983-1985)

The first commercial PC to use a graphical interface and then-cutting-edge concepts like preemptive multitasking, the Lisa was supposed to reinvent the new field of PCs. The baby of Apple co-founder Steve Jobs, the Lisa was slow, ungainly, and amazingly expensive at $10,000. Subsequent models (the Lisa 2 and Macintosh XL) improved and were cheaper, but the damage was done: In 1986, Apple let Lisa and Mac XL owners trade them in and buy a $4,100 Mac Plus for $1,500.

The silver lining? Lisa led to Jobs taking over Apple’s other PC under development; the resulting 1984 Macintosh took the same GUI and cutting-edge concepts and delivered them for less ($2,000), thereby reinventing the PC and “inspiring” competitors to use the same concepts.

2. Macintosh Portable (1989-1991)
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2. Macintosh Portable (1989-1991)

The 16-pound behemoth had many cutting-edge technologies for the time, such as its active matrix LCD screen, but its weight and the fact that it often would not turn on even when plugged in due to its battery design kept it off users' desks. While comparably bulky "luggables" such as the Compaq Deskpro were acceptable in 1986, by 1989 Toshiba and others were shipping the 6-pound notebook form we still use today, making the Macintosh Portable a whale in a market of dolphins. The PowerBook series introduced in 1991 didn't suffer from the Mac Portable's flaws and soon became one of Apple's most successful product lines ever, with its current descendant, the MacBook Pro, reigning as Apple's top-selling computer.

3. Apple Newton MessagePad (1993-1998)
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3. Apple Newton MessagePad (1993-1998)

Apple pushes the technology envelope, pioneering many technologies, but sometimes it overreaches, as was the case with the Newton MessagePad, a tablet-PDA hybrid with handwriting recognition. There was nothing else like it, but its ungainly size, woeful battery life, and hard-to-read screen relegated it to technology-cult status. As is often true with Apple, its innovations lived on, with its handwriting recognition forming the basis of the gesture technology used in the iPhone. The Newton also inspired 1996's Palm Pilot, which used many of the Newton's ideas in a size that made it easy to carry around. And of course, in 2010, Apple perfected the concept, with the release of the iPad, spawning the tablet era once and for all.

4. PowerBook Duo series (1992-1992)
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4. PowerBook Duo series (1992-1992)

Although well-regarded, the PowerBook typically followed the lead of PC notebooks, lagging months behind the competition. In the early 1990s, PC makers created executive-class, lightweight, lower-performance "subnotebooks," and Apple followed suit with its PowerBook Duo.

The Duo sacrificed too much to be usable. The keyboard (88 percent standard size) was hard to use, and the passive-matrix screen was difficult to view. There was no Ethernet port; instead, you had to use a pricey dial-up modem that made data exchange painful. The multiple dock types confused buyers and often forced them to own multiple docks (for home, office, and travel).

The thin-and-light MacBook Air is the closest thing to an Apple subnotebook today, one that offers far fewer compromises than the Duo did in its time.

5. Macintosh Performa series (1992-1997)
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5. Macintosh Performa series (1992-1997)

Facing criticism as a purveyor of elitist, pricey computers and increased competition from DOS- and Windows-based PC makers, Apple's then-CEO Michael Spindler decided to sell a line of cheap Macs called the Performa. And they were cheap: flimsy, prone to failure, and underpowered -- yet still costlier than a cheap PC. Worse, they cannibalized the sales of pricier Macs for a while, rather than expand the market.

The Performa experience would inform Apple’s business strategy from then on. It was one of the first projects Jobs killed when he ousted embattled CEO Gil Amelio to return as Apple CEO in early 1997, and it remains the chief reason for Apple’s ongoing avoidance of the low end of the PC, smartphone, and tablet markets.

6. eWorld (1994-1996)

6. eWorld (1994-1996)

Once upon a time, America Online ostensibly owned the Internet. Most users went through AOL to access Web content, and AOL made a fortune charging publications and service providers for space on its service. Apple cloned the idea for the Mac community, naming its proprietary "avoid the scary Web" destination eWorld.

The cartoonish service looked silly, and then-CEO Michael Spindler, who had withheld marketing support, ultimately decided Apple couldn't compete with AOL, pulling the plug on eWorld. Instead, Apple helped AOL develop a Mac client for AOL.

Ironically, AOL's Steve Case got his start in online services managing Quantum, the provider behind eWorld's predecessor, AppleLink. But Apple and Case had a falling out, and Case went on to develop AOL.

7. Pippin (1995-1996)
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7. Pippin (1995-1996)

In the mid-1990s, Apple was consumed by corporate drama, confronted by a resurgent Microsoft fueled by Windows 95, and struggling to keep up its mystique of quality and innovation. Engineering groups had tons of pet projects under development in an almost "throw it against the wall" culture, with many wanting to take Apple into new markets. The result was a project called Pippin, a multimedia PC aimed at gaming and CD playback -- like what a PlayStation or Xbox is today. Apple didn't make the Pippin; it licensed the design to companies like Bandai and Katz Media. But the PlayStation, Nintendo, and Sega consoles were already out and more popular, so game developers and users ignored the Pippin.

8. Copland OS (1994-1996)
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8. Copland OS (1994-1996)

When Gil Amelio took over in 1994, Mac OS was long in the tooth, with Windows 3.1 rising. Applications had grown in sophistication, and the OS needed an overhaul to support them. Amelio prioritized the development of a new OS, code-named Copland, which the engineering team quickly expanded in scope, developing technologies like OpenDoc and QuickDraw GX, before fully baking the core.

Apple demoed Copland in 1995, but its primitive microkernel didn't support symmetric multiprocessing, and the proto-Copland OS was highly unstable. Amelio brought in Ellen Hancock from National Semiconductor to save Copland, but her investigations showed it was hopeless, so Amelio killed Copland in 1996, a move that ultimately led to the return of Steve Jobs and the advent of Mac OS X.

9. Macintosh clones (1995-1997)
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9. Macintosh clones (1995-1997)

In the mid-1990s, Apple was falling apart, so when IBM and Motorola, which were trying to stop the "Wintel" juggernaut, came knocking, the so-called AIM alliance seemed like a lifeline, opening the door to clone licensing.

With IBM's encouragement, Leading Edge founder Stephen Kahng started Power Computing to produce Mac clones. As the main Mac clone maker, Power Computing was very successful. Its clones cost less and soon surpassed Apple's own Macs in ratings, and Apple began losing to its own licensees.

When Jobs returned in 1997, he decided he could fix Apple without outside help and killed the clone experiment by releasing Mac OS 9, a minor upgrade not included in clone licensing deals. Apple bought Power Computing and shut it down that year.

10. Apple USB Mouse (1998-2000)

10. Apple USB Mouse (1998-2000)

After taking back control of Apple in 1997, Jobs redefined the look and feel of the Mac, creating the candy-colored iMac line. Supporting the then-new USB standard, Apple decided to reinvent the look and feel of the mouse as well. The result was the yo-yo-like USB Mouse, aka the "hockey puck mouse." The disc design got attention for the wrong reasons: It didn't fit most people's hands. A thriving business soon emerged selling snap-on covers to fit your grip.

Unfortunately, Apple remained in full-arrogance mode, with Jobs and other executives carrying about like prima donnas who simply couldn’t understand why anyone would question their sensibilities. Not until 2000 did the company release the soapbar-shaped Apple Pro mouse, whose elongated form factor better fit human hands.

11. Power Mac G4 Cube (2000-2001)
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11. Power Mac G4 Cube (2000-2001)

Apple's fashionista kick also resulted in the G4 Cube, a crystal-box computer reminiscent of Jobs’ black Next Cubes from 1990-1993. As in much of fashion, function took a backseat to form. The G4 Cube had no room for full-length expansion cards, its acrylic enclosure and lack of fans (to keep it quiet) meant it tended to overheat, and it lacked audio input. But its spare styling lives on, in the burnished aluminum Mac Mini, which came out in 2005.

The G4 Cube wasn’t Apple's first fashionista foray; the 1998 iMac played with translucent plastic and unconventional shapes. But before that, the final days of Gil Amelio saw the $9,000 Twentieth Anniversary Mac, which mimicked Bang & Olufsen's high-end stereo equipment to little success.