One of the few places I still spot print copies of The Seattle Times is lounging, in news boxes, on street corners like lonely, aging prostitutes, whom I imagine are contemplating how they might reinvent themselves or turn back the clock for another pay day.

The latest attempt at such is to begin charging for digital access, a move announced Sunday in a column by David Boardman, the newspaper’s executive editor.

This is not a novel idea. As Boardman points out, more than 400 daily newspapers across the country have instituted some kind of digital pay wall. That The Times has waited to make itself No. 400-plus on the list does not portend well for future success.

After a 17-year career at The Times, I left 13 years ago for subscription-model Internet startups, where I immediately started fretting over the possibility (probability, I feared) of sleeping newspaper giants awakening to finally wall off and charge for specialty content, in the process making us Internet upstarts go poof in the digital cloud. I believed then that newspapers could overwhelm us with manpower and outmaneuver us with a physically and philosophically superior newsgathering infrastructure, tried and trusted for more than a century. But that never happened.

More than a decade later, the Times seems not to have learned many lessons from an industry death march that claimed even its main competitor, the Post-Intelligencer, and turned it and every other newspaper in the country into facsimiles of floundering Major League Baseball teams forced to dump salaries at the trade deadline. The newspaper claims nine Pultizers, but fields a staff dramatically reduced from its hey day and its website has no extraordinary features.

The New York Times is an example of a newspaper that actually positioned itself to offer a digital product. The NYT made some initial stumbles, but constructed its digital future upon an existing foundation of journalistic authority and breadth. It has become the gold standard in mainstream, multimedia and digital explanatory journalism. It publishes one of the liveliest, most influential weekly magazines anywhere, and includes it both in its Sunday print editions and online. Though sometimes the result of being one of the few left standing in some categories, the New York Times has become a quintessential source for narrower subject spaces such as the arts, fashion and science.

And though not always first to report developments in the increasingly Twittersperically tilted, nano-second-gradated news autobahn, the New York Times frequently is first to credibly report them. Credibility may be valued in some part as a backlash to the Web-accommodated, anything-goes “news” environment, but you take your virtues where you can get them these days.

The Seattle Times’ road to a digital tollbooth feels GPS-challenged and littered with potholes by comparison. The way I saw things, as far back as when the Web rebooted as a business platform about a decade ago, The Times had three very saleable assets to offer on the Web: its dynamic and highly respected sports staff, a staff of photojournalists that was the envy of much of the industry, and the promise of arts and entertainment. Though The Times back then had strong local and regional news desks, I did not include them because general news already was being rendered a commodity on the Internet. Business coverage could have been an intriguing candidate.

On the entertainment front, I would have compiled the most thorough listings available, curated and rated the best of them, and packaged it all with reviews, more extensive previews, profiles, arts business news and offerings from what back then was a pretty robust food and dining staff. No matter how plugged in, no user looking to be fed and entertained possibly can stay on top of performance schedules or openings and closings, not to mention the rhythms of nationally relevant events like the Seattle International Film Festival, Bumbershoot and The Bite of Seattle. This product may not have been the biggest digital seller, but in time it all could have been folded into a mobile app and layered with location services and become pretty indispensible.

No one has done the aforementioned, on the scale it had the potential to be, but a newspaper looking to takes on arts and entertainment today would be starting behind alternative weeklies, monthly city magazines, and a cadre of bloggers with a lot more specialized knowledge.

Creating a product from an elite photography staff would have required creativity and foresight that maybe didn’t exist anywhere, though I will remind that The Seattle Times has been at the forefront of many visual revolutions in the newspaper industry. To start with, there would have been a surplus of pleasing, artistic images to offer; I’m not only a photographer but have packaged content both in print and online, so I know that for every image used in a newspaper like the Times, there were several, almost as good, that went to archives, some never to re-surface. Back then, images were starting to be paired with sound to offer a more immersive experience; The Times still was traveling all over the world and could have taken users to places they could not go. Eventually, high-quality video stories would have been included in a mix that would have been even more compelling in the days before smartphones and more sophisticated consumer cameras created the illusion that anyone could do “what the pros do.” When that time came, you could have paraded your celebrity photographers in lucrative, how-to (or how-I-got-this-picture) workshops.

Instead, the Times photojournalism staff initially was blocked from the newspaper’s glacially slow transition to multimedia platforms. Meanwhile, its online editors were branding themselves at industry conferences, advocating digital journalism on the cheap, ignoring that the next-generation audience it needed, but was failing to win, grew up on large helpings of definition-rich graphics, much of it served up on video games. The enduring symbol of that era for me is the desultory scene streamed from a low-resolution camcorder in a parking lot before a Seahawks game. This induced the two-note death knell for any Web enterprise — yawn, click.

I might be biased because it’s where I came from, but sports offered the biggest pot of gold for newspapers like The Seattle Times. Considering the Super Bowl is the highest rated broadcast in any given year, how many billions of entertainment dollars are spent, and how strong affinities with teams can be, no wonder many consider sports to be among the most recession-proof businesses around.

During its prime , the Times had a team beat writer, a sport- or league-specific columnist, general columnist and at least one photographer assigned, during the season, to an NFL, NBA, Major League Baseball and college sports (mostly, football) team and today you would imagine soccer being in the mix. Maybe you throw in chat, message boards and the occasional guest column by a coach or player. Based on my experience at successful subscription-based, sports media businesses, I could imagine charging a monthly fee (say, $3.99) for a single sport or (say $7.99) for all sports, with discounts for annual subscriptions.

Until the past year, I might have guessed that sports coverage, though a shadow of its former self, still was vital enough to be an attraction for the digital subscriptions The Seattle Times will begin offering in March. However, desperate to retain employees at current pay levels, as well as misinterpreting the trend of individual branding, The Times has allowed too many cats to break from the herd. When a digital entity begins to charge for access, efforts to circumvent immediately commence. You could drive an NBA player’s Humvee through the holes already forming in The Times’ pay wall.

If you want the thoughts of Jerry Brewer, The Times’ best (and now only) sports columnist, or beat writer Danny O’Neill’s insights into the most popular team in town, the Seahawks, they both co-host sports-talk radio shows on a daily or almost-daily basis. Most other Seattle Times sportswriters also are radio regulars. Everyone on staff will feel pressure to continue breaking news, in 140 characters or less, on social media. Several do so now on their own feeds (which are not necessarily controlled by their company, as the New York Times discovered). If blogs are not going behind the Times’ pay wall, feast until you burst on Mariner news and views because (the especially Internet savvy) Geoff Baker and Larry Stone are prodigious, as well as informative and entertaining, bloggers.

Can you start to see what might have been? Maybe these three products start funding their own staffs and production, even start making a profit (remember, we started these 10 years ago) and help the print edition cover the rest of the operation. Maybe you put local and regional coverage, as well as singular voices such as Danny Westneat and the vastly underutilized Ron Judd, online and sell ads against them. Maybe in time, you unearth a digital strategy for them, too.

Instead, The Seattle Times has diluted the value proposition of its digital product, failing to add to and improve its online offerings, and then is attempting to charge almost as much as the New York Times. (I’ll pay the extra 11 pennies a week for the authority, overall breadth and intelligence, the multimedia, timeliness, etc., etc., etc.). The Seattle Times is repeating a mistake almost every other newspaper is making: It is treating its website like a distant cousin and “including” it with a print subscription instead of, ala the Wall Street Journal, developing two different products and subscription-revenue streams, print and digital, yielding true bundling options.

The Seattle Times also is following its newspaper sisters and brethren off the cliff with a fundamental misapplication of print mentality to digital reality. A physical newspaper is a browsing medium; in other words, readers flip through pages to find items of interest. Virtually nothing on the Internet truly replicates that experience. On the other hand, though people will say they are “browsing” the Web, and use a browser to do so, the Internet is a destination medium. Users employ “addresses” to “navigate” to content. Being presented a list of hyperlinks may resemble the browsing experience, but one first must find the list, often by employing effective terms in a search.

There really is no leafing through a website. And newspapers tend to suffer on the Internet because they produce massive amounts of daily content that is too generalist in an environment demanding more specificity. With a discrete product like, say, pro-football team coverage, a newspaper gets a branding head start, with the benefits of giving people exactly what they want, on a platform where they expect exactly that. It’s mind numbing that newspapers are so counter-evolutionary, choosing extinction over true transformation.

You’d have thought, or hoped, that The Seattle Times was so late to the digital party because it was developing something truly ground-breaking. The print media industry as a whole went kicking and screaming out of analogue, and it’s a wonder that a newspaper that serves one of the most digitally enlightened regions in the world kicked and screamed longer than most. The damage inflicted by all the hesitancy may never be repaired, even by the likes of the New York Times and Wall Street Journal. Yet, after more than a decade of helping train users to expect news to come free, without awareness of, or regard for, the cost of producing it, all The Seattle Times proposes to do is declare the party to be over because it no longer can afford to keep it going.