The New York Observer's Trump ProblemS

Pouty fathead Donald Trump is a tailor-made character for the New York Observer, which purports to monitor Manhattan's smug oligarchy with a gimlet-eyed detachment. And his semi-coherent presidential grumblings, which count as news just about everywhere else, make ideal grist for the Observer's mill. Too bad he's the owner's father-in-law.

Here's a sentence that someone ought to write about Trump: "The Donald's incredible bullshit machine keeps churning up the landscape, spewing forth a plume of chutzpah that might have made even P.T. Barnum a bit queasy."

Actually, that was written about Trump, and published in the Observer, 13 years ago.

It's an attitude that the Observer has taken toward Trump for decades, forged by former editor Graydon Carter, who had, during his days at Spy magazine, helped brand the man a "short-fingered vulgarian."

But lately, especially in the month or so since Trump began loudly and stupidly asserting that Barack Obama was born in Kenya and grunting about a presidential run, the paper has been practically silent on the subject. Incidentally, the Observer is currently owned by Jared Kushner, who is married to Trump's daughter Ivanka.

Since early March, when Trump's latest eruption began in earnest, the Observer has published just two substantive pieces on him: A no-frills account of his Comedy Central roast, and a critical analysis of recent polling showing him leading or tied for the GOP nomination—penned by a freelancer—published this morning. Both were online-only.

Trump was mentioned in several brief blog posts, the most involved ones picking up stories about his habit of mailing defaced printouts of web stories to his critics, his booking appearances in Iowa, and an on-screen tiff with Rep. Anthony Weiner. And one editorial about the absurdities of modern life in New York (you don't say?) mentioned Trump's pseudo-candidacy in an aside.

The New York Observer's Trump ProblemS

But the story about how one of New York City's most storied and familiar figures has openly embraced a racist lie? It's AWOL.

As is the one about how Trump is once again expertly manipulating the press with empty boasts—it used to be known as a "bullshit machine"—about running for president in a bid to get attention. As is the one about how Trump's rarefied social circle is reacting to his new xenophobic turn. As is the one detailing the aspects of Trump's lavish lifestyle that his newfound friends in the Tea Party might not identify with. And so on.

When Politico's Ben Smith and I began noting via Twitter this week that the Observer seems to be abdicating a historical duty to weigh in on the intersection of wealthy dimwits, ego, reality TV, a complicit media, and the general dumbfuckification of our political culture, the paper's editor Elizabeth Spiers shot back: "Guys, we are covering it! (Which you'd know if you actually called me—or asked)," apparently establishing a new standard for reported observational Tweeting. Spiers later added, also on Twitter, that a "larger piece is in the hopper." Asked to elaborate on the record, she said only, "We're covering trump the same way we would any other prospective candidate at this stage in the election cycle." Last month, she devoted a detailed, nuanced 2,600-word feature to the prospects of Rudy Giuliani, another New York fixture and prospective candidate whose current support appears to have been eclipsed by Trump's. Asked if his paper would have any trouble covering his father-in-law's political machinations, Kushner referred questions to Spiers.

The New York Observer's Trump ProblemS

Spiers is in a spot. There's not an easy answer to the question of how your newspaper should appropriately cover your boss' loathsome father-in-law. She could swear off Trump entirely, publicly acknowledge that there's really no way to fearlessly cover him in that situation, and leave it to others. But that would be untenable if he actually does run and becomes part of the 2012 race. Or she could fire away for as long as Kushner is willing to put up with it. But the current strategy, with Trump sort of loitering around the edge of the Observer's coverage—and frequently without a disclosure of his relationship to Kushner—while he's in the middle of what certainly looks like another swindle, feels awkward for everyone.

And it kind of undermines the point of the New York Observer. Which, we should add, was recently clarified and reinforced by Spiers, who restored its old motto to the front page: "Nothing sacred but the truth."

Disclosure: I've written for the Observer and have friends who work there. And Spiers served as editor of Gawker from 2002-2003.

[Photo of Donald Trump via Getty Images. Photo of Jared Kushner and Ivanka Trump via Joe Schildhorn/Billy Farrell Agency]