It appears to be Pick On News Web Designers Day today. This comic — poking at news sites’ unwillingness to link, misuse of thumbnails, and addictions to share buttons, among other things — made the rounds of Twitter, to the point of crashing cartoonist Brad Colbow’s site.

But even more talked about, on Hacker News anyway, was web designer Andy Rutledge’s unrequested redesign of the website of The New York Times. He finds the current site too busy, too data-dense, and he suggests an alternative, here. (That’s specifically a section front for Politics; you can see the existing page on nytimes.com here.)

Rutledge’s design has a lot to recommend it: it’s clean, spacious, has nice typography, and feels high-end, the way something like the Times should to differentiate itself from the competition. (I’m focusing just on his design rather than his ideas about journalism, which are pretty wrong-headed and seem derived from some more-puritan-than-the-Puritans ideal — how free news is inherently bad, that the act of “featuring” some stories over others is a violation of news purity, “there is no ‘most popular’ news,” “almost all news organizations have abandoned reporting in favor of editorial,” etc.)

But as nice-looking as it is, it also misses some of the point of what it means to design for the Times. The Times generates a ton of content every day. Looking at Times Wire, I see 169 stories published just in the past 18 hours — and I don’t believe that’s actually capturing everything that flows through the Times’ blogs and sundry other online spaces. And it’s a Tuesday! The challenge of a news organization that pumps out that much content is how to present it all in a way that maximizes its value, both journalistically and financially. There are many, many beautiful websites around the Internet that, as lovely as they are, would be awful as an entry point of a news site. (Similarly, stripping stories down to just headlines — no intro text, which Rutledge dislikes for some reason, no thumbnails — may maximize typographic beauty, but it doesn’t do much for enticing a click.)

This isn’t just a problem for the Times; it’s also a problem for the massive aggregators like HuffPo and Gawker. (Whatever one thinks of the controversial Gawker redesign, it is nonetheless an attempt to wrestle with this problem.) Rutledge’s design, on a commonly sized laptop screen (1440×990), would link to exactly three stories in the first screenful of content. The Times’ current Politics page links to 13.

Now, that doesn’t mean the Times Politics page is perfect. It’s actually kinda ugly, and confusing, and cramped. But, as ex-Timesman Michael Donohoe writes at Hacker News, it’s also based on a design that’s approaching six years old. (Here’s the front page of nytimes.com on April 2, 2006, when the current design was put into place. Look familiar?) That raises another of the major challenges news sites face: Because they produce so much content, every day, nonstop, major change is hard to pull off. That’s true with any extensive website, but it’s particularly true of a news website that takes its responsibilities to the historical record even a little bit seriously.

Think how much the Times’ digital output has changed since 2006, how many new targets those stories hit — an iPhone app, an iPad app, a Kindle edition, a mobile site. And each of those, I’d wager, meet more of Rutledge’s wishes: they’re cleaner, more spacious, more obvious nav targets. And the bits of nytimes.com that have gotten designed/redesigned since 2006 — DealBook, Opinion, T — all share that spirit.

(And if Rutledge really does want nothing more than a long stream of decontextualized headlines, may I suggest either Times Wire or Today’s Paper?)

The legitimate question is why hasn’t the front page of nytimes.com seen that same kind of love. I suspect the institutional inertia question is a big part of it. I suspect another is the Times’ strong print DNA, which privileges the editor’s judgment in story placement in ways that lead to echoing of complex, text-heavy print layouts that match the Times-on-paper.

But the other piece is that no one has figured out a way to present lots and lots of constantly updated information in a way that (a) is beautiful, (b) is effective at story discovery, and (c) privileges editorial control.

Beautiful by itself isn’t that hard — there are lots of beautiful sites on the web, and lots of talented designers. When it comes to effective story discovery, the innovation has all been in the direction of algorithms and raw feeds. An algorithm is how Facebook surfaces items in your News Feed; a raw feed is how Twitter organizes tweets from the people you follow, in straight reverse chronological order. But neither of those is perfect for human editorial control, which is something news organizations rightly value; there are tons of visual and contextual cues on those complicated nytimes.com pages that tell me what Times editors think is more or less important for me to see. (And, in any event, most news organizations have nothing near the amount of data needed to create Facebook-style personalization. The Times, with its article recommendations, is about as close as it gets.)

I guess my overarching point is that, while there are no doubt lots of pages on nytimes.com or any other news site that could use a once-over, the problems of large-scale information architecture for news sites are really hard problems. Smart people think about these problems. And their solutions require more than a nice slab-serif typeface and some white space.