Actually, Steve Jobs did try to buy Dropbox years ago, Dropbox's owners say, and they turned him down. Still, we can fantasize about how wonderful it would be if, in a renewed effort, Apple could convince Dropbox to sell. Except that we would be wrong. The fantasy isn't that Apple might someday acquire Dropbox; the fantasy is that its doing so would work out well.
The reason that iCloud doesn't function like Dropbox is not that Apple's engineers aren't capable of doing a better job. Nor is it that they made decisions about iCloud's design that they now regret. Apple knew exactly what it was doing and accomplished exactly what it intended. Apple doesn't want iCloud to work like Dropbox. Instead, Apple is committed to a sandboxed approach that it originally implemented on iOS devices. Rather than loosening restrictions over time, Apple has extended sandboxing to Mac apps sold through the App Store. Limiting user access to where documents are stored and restricting documents to the apps that created them--this is all part of a deliberate strategy by Apple. Similarly, on iOS devices, Apple continues to prohibit users from installing apps that do not come from the App Store or accessing root level files; you need to jailbreak your device to gain such access.
Why is Apple so insistent on sticking to this restrictive approach? The consensus favorable viewpoint is that these prohibitions offer security advantages, better quality control, and a more consistent user interface. Whatever the reasons, limiting user access to software and hardware has been part of Apple's vision from the earliest days of the Mac. The original Macintosh, in contrast to every other computer at the time, was designed so that the typical user could not open the case. Today's MacBook Pros with Retina Displays continue this tradition. Kyle Wiens, of Ifixit.com, has described them as "the least repairable laptops" he's ever taken apart. While many view this negatively, it is consistent with viewing Apple's devices as "consumer electronics" rather than "old-style computers." After all, how often do you want to take apart your flat-screen television?
All of this leads me to conclude that, if Apple did ever buy Dropbox, it would kill Dropbox--after possibly retaining a few of its lesser features for iCloud. It would likely play out similar to the story of Apple and Lala.
Still, I'm not losing sleep over this possibility. That's because I don't think it will ever happen. Apple knows that Dropbox isn't the only game in town anymore. To be completely successful, Apple would need to start playing Whack-A-Mole, killing each competitor that ascended to replace Dropbox. Apple isn't going to do this. So it will likely do nothing.
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