Rotten Apple: Apple’s 12 Biggest Failures

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

Mac OS X, the iPod, iTunes, the iPhone – 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 12 worst failures to date.

Related stories:

Mac OS X Snow Leopard: What’s new for all users

Deathmatch rematch: BlackBerry vs. iPhone 3.0, side by side

Apple betrays the iPhone’s business hopes

Top 10 features that Apple stole from Windows

Follow the latest developments in Macintosh and Apple at InfoWorld.com.

1. Apple Lisa (1983-1985)

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

However, Lisa’s failure drove Jobs in 1982 to take over the other Apple PC under development. This led to 1984’s Macintosh, which took the same GUI and other cutting-edge concepts and delivered them for less ($2,000). The Mac did reinvent PCs, causing other companies to use the same concepts, with Windows 3.0 finally emerging as the most popular, though less sophisticated GUI.

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)

Apple usually pushes the technology envelope and pioneers many technologies. But sometimes it overreaches, as in the case of 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. But as is often true with Apple, its innovations lived on, with its handwriting recognition still used in the Mac OS X’s Ink control panel that appears when a pen tablet is connected and that helped form 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.

4. PowerBook Duo series (1992-1992)

Although the PowerBook was well-regarded, Apple typically followed the lead of PC notebook makers and lagged months behind the competition. In the early 1990s, PC makers started creating executive-class, lightweight, but lower-performance “subnotebooks,” and Apple followed suit with its PowerBook Duo.

But it sacrificed too much to make the Duo really usable. For example, the small keyboard (88 percent standard size) was hard to type on, and the passive-matrix screen was difficult to view. There was no Ethernet port (Wi-Fi didn’t exist back then); instead, you had to use a pricey dial-up modem that made data exchange painful or by a separate dock. The multiple dock types confused buyers and often forced them to own multiple docks (for home, office, and travel); users also complained that they brought the “wrong” dock with them when on the road.

The thin-and-light MacBook Air is the closest thing to an Apple subnotebook today, and like the Duo it skimps on ports. But it offers far fewer compromises than the Duo.

5. Macintosh Performa series (1992-1997)

Long criticized as a purveyor of elitist, pricey computers and facing 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. When Apple allowed other PC makers to develop and sell Mac clones, the Performas suffered even more, as those clone systems tended to match the features of the top Mac models at Performa prices.

If you want to know why Steve Jobs won’t let Apple sell cheap Macs, refer to the Performa experience; it was one of the first projects Jobs killed when he ousted embattled CEO Gil Amelio to return as Apple CEO in early 1997. Jobs put Apple back on the track to producing only high-quality products, a strategy that has served Apple well ever since.

6. eWorld (1994-1996)

It’s hard to remember now, but for a while, America Online almost owned the Internet. Most users went through AOL to find and access Web content, rather than via a browser to get to the Internet directly, and AOL made a fortune charging publications and service providers to get a space on its service. Apple, having aspirations to be a monopoly, cloned the idea for the Mac community and named its proprietary, “avoid the scary Web” destination eWorld.

The cartoonish service looked silly, and Apple was in the midst of a corporate management drama that almost killed the company. Then-CEO Michael Spindler withheld marketing support and ultimately decided that Apple couldn’t compete with AOL and pulled the plug on eWorld. Instead, Apple helped AOL develop a Mac client for AOL and got out of the online-service business.

Ironically, AOL’s Steve Case first got his start in the world of online services by managing Quantum, the provider behind eWorld’s predecessor, AppleLink. But Apple and Case had a falling out, and Case went on to develop AOL, while Apple turned to GE Information Services to run eWorld.

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. (Around this time, Apple also sold QuickTake cameras, but these were relabeled products produced by others.) Plus, Apple has a strong reputation in Japan, which it wanted to deepen.

The result of all this was a project called the Pippin, a multimedia PC aimed more at gaming and CD playback than traditional computing — more like what a PlayStation or Xbox is today. Apple didn’t make the Pippin; it licensed the design to companies such as Bandai and Katz Media that created gaming consoles from it. But the PlayStation, Nintendo, and Sega consoles were already out and more popular, so game developers and users ignored the Pippin. Pundits also considered the Pippin to be yet another distraction for an already distracted Apple.

8. Copland OS (1994-1996)

In 1991, then-CEO John Sculley focused more on marketing than investing in a new OS. When Gil Amelio took over in 1994, he made the development of a new OS, code-named Copland. The engineering team developed a string of technologies such as OpenDoc and QuickDraw GX, but failed to get the core features to work. Apple demoed Copland at its WWDC show in 1995, but proto-Copland OS was highly unstable. Ellen Hancock from National Semiconductor tried to save Copland, but it was hopeless, so Amelio killed it in 1996. The project to save Apple’s future looked as if it might hasten its demise instead. So Amelio tried a Hail Mary and began shopping outside Apple for a replacement. He came close to buying the Be OS from former Apple Mac development chief Jean-Louis Gassee, but Gassee wanted more money than Apple would pay. Amelio then turned to Steve Jobs, hoping to adopt his NextStep OS as the basis for the new Mac OS. The deal was done and Jobs returned as CEO. NextStep formed the basis for the new Mac OS, called Mac OS X, that more than a decade later is considered the best PC OS available.

9. Macintosh clones (1995-1997)

In the mid-1990s, Apple was falling apart. CEO John Sculley departed in spectacular fashion after the board lost confidence in the ex-PepsiCo executive’s hype-heavy style, and new CEO Michael Spindler was trying to refashion Apple as a typical PC maker, which had Apple’s engineering staff in open revolt. At the same time, IBM and Motorola were trying to stop the “Wintel” juggernaut, so they proposed that they and Apple develop a computer that could run Mac OS, IBM’s OS/2, and Microsoft Windows NT, using IBM’s and Motorola’s PowerPC chips. Microsoft killed the NT for PowerPC edition, but the so-called AIM alliance opened the door for Apple to consider letting other companies make and sell Macs. The main clone maker was Power Computing, whose founder Stephen Kahng started the wildly successful Korean PC maker Leading Edge. With IBM’s encouragement, Kahng was willing to start up Power Computing to produce Mac clones. Power Computing’s clones cost less and soon surpassed Apple’s own Macs in ratings by Macworld and MacUser magazines. Steve Jobs returned to Apple in 2007 and quickly killed the clone experiment by releasing Mac OS 9. Apple bought Power Computing and shut it down that year.

10. Apple USB Mouse (1998-2000)

After taking back control of Apple in 1997, Steve Jobs went about redefining the look and feel of the Mac itself, and his design team created the candy-colored iMac line that contrasted dramatically with the traditional beige box. When Apple began supporting the then-new USB connection standard, it also decided to reinvent the look and feel of the mouse. The result was the circular, yo-yo-like USB Mouse, commonly called the “hockey puck mouse.” The disc design certainly got attention, but for the wrong reasons: It was hard to hold, as it didn’t fit most people’s hands. A thriving business soon emerged selling snap-on covers that made them fit your grip.

Apple at this time was in full-arrogance mode, with Jobs and other executives carrying about like prima donna fashion designers who simply could not understand why anyone would question their design sensibilities. But in 2000, the company released the soapbar-shaped Apple Pro mouse, whose elongated yet still-simple curves could be held comfortably and securely by humans.

11. Power Mac G4 Cube (2000-2001)

Apple’s fashionista kick also resulted in the G4 Cube, a crystal-box-style computer that was eerily reminiscent of the black Next Cube workstations that Steve Jobs was selling between 1990 and 1993. But 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 that it tended to overheat, and it lacked audio input. But its spare styling lives on, now in burnished aluminum, in the Mac Mini, which came out in 2005.

The G4 Cube was not Apple’s first foray into fashionista designs; the 1998 iMac was the first to play with translucent plastic and unconventional shapes. But even before that, in the final days of Gil Amelio’s regime, came the $9,000 Twentieth Anniversary Mac, whose sophisticated style mimicked that of Bang & Olufsen’s high-end stereo equipment. The TAM was hardly a success, but it was a one-time “art gallery” product never intended to be a mass-market hit (only 12,000 were made), so we don’t include it as one of our top 12 failures.

12. Apple TV (2007-present)

In recent years, Apple has deprived us of spectacular failures it supplied so generously from the mid-1990s to the early 2000s. Although its Mac Minis have been criticized as overpriced, they sell decently, and Apple’s desktop Macs fall into the category of competent. Instead of failures, the decade has instead been one of major hits such as the MacBook, MacBook Pro, iPod, iTunes, and iPhone. There’s been one exception so far: the Apple TV.

Apple’s networked media player box was supposed to be the new TiVo, but it’s not even as well liked as Windows-based media-center PCs. Apple TV is fairly limited: You can use it to play music and photos onto your TV from other computers or through iTunes as well as play videos from Flickr, YouTube, and the iTunes Store. But you can do the same plugging your computer into many HDTVs using its HDMI or USB port. Apple TV isn’t connected to the vast video libraries of Netflix or Blockbuster, so you’re stuck with the iTunes Store’s offerings, which many television and movie studios have avoided supporting for fear of suffering the same loss of control as the music industry experienced with iTunes. In other words, Apple TV isn’t that innovative or that capable.