Tim Bray has reasons for linking to a Wikipedia article about an organization rather than the organization’s site:

[A] lot of institutional sites are pathetic self-serving fluff served up in anodyne marketing-speak with horrible URIs that are apt to vanish.

Linking to the Wikipedia instead is tempting, and I’ve succumbed a lot recently. In fact, that’s what I did for the Canada Line. After all, the train is still under construction and there’s no real reason to expect today’s links to last; on top of which, the Line’s own site is mostly about selling the project to the residents and businesses who (like me) are getting disrupted by it, and the taxpayers who (like me) are paying for it.

Wikipedia entries, on the other hand, are typically in stable locations, have a decent track record for outliving transient events, are pretty good at presenting the essential facts in a clear, no-nonsense way, and tend to be richly linked to relevant information, including whatever the “official” Web site might currently happen to be.

I wrote something similar about a year ago:

I consider a Wikipedia link more usable than a link to an organization home page. An organization article will link directly to an organization home page, if the latter exists. The reverse is almost never true (though doing so is a great idea). An organization article at Wikipedia is more likely to be objective, succinct, and informational than an organizational home page (not to mention there is no chance of encountering Flash, window resizing, or other annoying distractions — less charitably, attempts to control my browser — at Wikipedia). When I hear about something new these days, I nearly always check for a Wikipedia article before looking for an actual website. Finally, I have more confidence that the content of a Wikipedia article will be relevant to the content of my post many years from now.

Why not preferntially link to Wikipedia? Bray feels bad about not linking directly to original content and says Wikipedia could go off the rails, though later provides a reason to not worry about the latter:

I’d be willing to bet that if Wikipedia goes off the rails and some new online reference resource comes along to compete, there’ll be an automated mapping between Wikipedia links and the new thing; so the actual URIs may retain some value.

Indeed; and the first argument explains why linking to Wikipedia is superior to linking to an institution. But what about “original content”? If the content isn’t simply a home page (of an organization, person, or product significant enough to be in Wikipedia), Wikipedia doesn’t help. For example, I linked to Bray’s post “On Linking”; only providing a link to his Wikipedia article would have been unhelpful. The Wikipedia article link in this case is merely supplementary.

So what to do to help with broken and crappy links to items not described in Wikipedia? Bray suggests “multi-ended links”. I think he’s on the right track, but this is not something a web content creator should need to worry about — robust linking need not involve choosing several typed (e.g., official, reference, search) links. The content creator’s CMS and the user’s browser ought to be able to figure this stuff out; the content creator should just use the best link available, as always.

Last year I wrote:

I predict that in the forseeable future your browser will be able to convert a Wikipedia article link into a home page link if that is your preference, aided by Semantic Mediawiki annotations or similar.

In the case of non-Wikipedia links (and those too), combatting linkrot and providing alternate and related (e.g., reference, reply, archival) links is an obvious feature add for social bookmarking services and can be made available to a CMS or browser via the usual web API/feed/scraping mechanisms.