The Chicago Tribune is a terrible newspaper that was driven into bankruptcy by timid bureaucrats posing as editors. So who is the New York Times hiring to launch its new Chicago edition? The same people that ruined the Trib.

The Times is rolling out a new two-page local-news section that will be inserted into its Chicago editions; the idea is to compete with the Tribune and Chicago Sun-Times for news and advertising. The paper is engaged in a similar effort in San Francisco.

Despite its manifest troubles, the Times is in a pretty good position to compete with the Tribune in Chicago, largely because the Tribune is as dull as a sack full of wet newsprint and suffers locally from a well-earned reputation for stuffy, censorious parochialism. The Times has always had a very good foothold in Chicago because there is no local alternative for the sort of people who read the Times—curious, smart, and not invested in Chicago's bottomless Second City status anxiety. The Tribune, on the other hand, is pitched directly at suburban blue-haired ladies who are given to write angry letters to the paper, and the definition of a successful editorial initiative at the Trib is one that does not generate angry letters from blue-haired suburban ladies.

But the Times isn't actually getting into the local news business in Chicago itself; instead, it is outsourcing the coverage to something called the Chicago News Cooperative, a newly formed non-profit designed to "provide high quality, professionally edited news and commentary to the Chicago region on the Web, in print and over the airwaves," according to a news release announcing its formation. So who's heading up CNC? Why, James O'Shea, the Tribune's former managing editor. On its board is Ann Marie Lipinski, the Trib's former top editor and O'Shea's former boss. And writing a column for CNC's "branded content" in the Times will be former managing editor for features Jim Warren. In other words, the Times is taking a whack at the Trib by hiring the people whose complacency and abject failure to create a newspaper worth reading made the Trib vulnerable to a whack-taking in the first place.

Your blogger knows something about that complacency because I labored under Lipinski, O'Shea, and Warren's "professional editing" at the Tribune for several years, as did my wife. The entire organization was seized by their collective panic at lowering revenues, plummeting readership (I quite literally never met a Tribune subscriber socially during my five years in Chicago), and frequently aborted frantic attempts to do something—hastily convened committees to launch new sections produced prototypes that languished for months and months in sad little piles around the newsroom as reminders of the paper's institutional paralysis. Meanwhile, there were days when the front page consisted almost entirely of wire copy, when editors picked up two-week-old Los Angeles Times stories to fill out sections, and when Lipinski reacted to the appearance of a bad word—actually, a cheeky, punny reference to a bad word in a headline—by dragging editors to the printing plant after hours and forcing them to physically remove the offending section from the next day's bundled editions.

And then there was the night that, after filing a story on Dan Rather, I went home to see if it had gotten any blog pick-up. I Googled for it, only to discover that it hadn't yet been posted on the Tribune's web site. But it had made it to the site of the Kansas City Star, which subscribed to the Tribune's wires. Lipinski and O'Shea's paper, in the nation's third-largest market, didn't get the story up until the next morning, because the web folks had gone home. But Kansas City's daily managed to get it out there for them.

Anyway, those are the folks who will be, in O'Shea's words, "adapt[ing] to new technologies and devis[ing] some creative, innovative ways to fulfill our obligations" as journalists. They certainly didn't get it right the first time; we wish them luck in this circle-back attempt.