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The Washington Post‘s Style section may be saying goodbye to its top editor, Deborah Heard, who has plowed 20-plus years of service into the paper. She is weighing an early retirement package.

“I’m still evaluating it,” says Heard. “I have had a lot of conversations with a lot of people because this is a big decision for me.”

Like many of her ranking colleagues at the Post, Heard feels the pull: The buyouts are generous, full of free money, benefits, and parachutes, courtesy of the company’s deep pension holdings.

Less clear is whether Heard may be feeling a push as well. Her section is the subject of considerable intra-newsroom sniping, much of it a lamentation of how far Style has fallen over the years.

Her boss, too, apparently feels there’s a content issue or two within the hive of critics and feature writers. Earlier this year, Washington City Paper interviewed Post Executive Editor Leonard Downie Jr. about Style’s fraught relationship with washingtonpost.com, a platform whose managers have declined to give Style the presence and cohesion that the section enjoys in print. Downie steered the discussion away from Web considerations:

“What we want them to focus on. ..is making sure that Style itself in the print newspaper is as strong as it can be, because it’s been such a great section that all the other sections of the newspaper steal from it all the time. So their focus really ought to be on producing really good, avant-garde journalism that will both create the strongest possible print section and give the Web really good stuff.”

Really good avant-garde journalism—-that’s a pretty demanding standard, and any Style editor knows about standards. Style is one of those properties that was always better in the past, back when so-and-so was writing gorgeous narratives for the ages and so-and-so was shaking the Washington establishment down to its English basements. The glory-days boilerplate threads from Ben Bradlee, the former top Post editor who created Style in 1969, and through various other legendary Posties, such as…well, let the Washingtonian‘s Harry Jaffe supply the historical perspective:

More than a few readers still pine for the generation of writers who once made Style a fun and feared read. Sally Quinn made her mark writing irreverent profiles of the political and social set. Style had brassy writers like Myra McPherson, Lynn Darling, Stephanie Mansfield, and Judy Bachrach. Amazing voices like Marjorie Williams. They described the social scene and then undressed it.

Man, they were awesome way back when!

Though no contemporary version of Style will ever compete with its mythologized past, the current product often fails on its own terms. Sure, the critics still do solid work and the Reliable Source is a reliably fun read. And credit Monica Hesse for injecting a bit of life into the coverage.

But the section’s iconic feature hole has become something of a stink pen. Memorable stories just don’t pop up in that space with enough frequency to make it something that absolutely must be checked before heading out the front door. Part of the problem is that the section’s best essayist and maven of pop culture, Hank Stuever, has spent a goodly part of the last two years working on a book about Christmas in the suburbs.

Another part of the problem is DeNeen Brown, a fine reporter who has overwritten many a feature piece on the District in her Style tenure. Her thing is all about integrating storytelling devices from fiction into her journalism, and Heard’s Style section gives her the freedom and space to do so. Never have freedom and space been so miserably allocated.

Brown’s pieces tell the story of a writer in need of plain English, plus some self-awareness. She is the queen of the second person, the deeply annoying second person, the last person you want showing up in in your Style section. From a recent piece on war:

War, sanitized by distance, lives abstractly on television; you watch it from your brown corduroy sofa, in your cul-de-sac, flipping channels. You have the luxury of hitting the remote and turning the volume low as you hear another report of U.S. soldiers killed, Iraqis killed, insurgents, roadside bombs, corpses. Or change the channel, skip the carnage. Or watch, and listen, because something — you don’t know what — draws you in.

Here’s the lede to a Brown story from last year on the longevity of crack cocaine:

If Crack had a face, what would it look like?

If Crack had a child, what would it name him?

If Crack drove a car, what kind of car would it be?

And if crack were an editor, what moronic lede would it kill without mercy?

A less subjective failure for Style under Heard is the politics reporter position. Last year, she hired Sridhar Pappu, a former scribe for the New York Observer, to nail the various narratives of the 2008 campaign and beyond. Pappu flopped and left the paper earlier this year.

One more thing: The combined Sunday Style & Arts section reads like the worst of both worlds.

Anyhow, the real crisis at Style may be that the rest of the newspaper has caught up to it. The A section has Dana Milbank writing on-the-spot narratives about politics; Metro these days does wonderful work with its own feature spot, as does Business; and if anything characterizes Sports under Emilio Garcia-Ruiz, it’s lots of interesting feature-writing, even in its blogs. (Well, at least the D.C. Sports Bog, written by Dan Steinberg (Friend).)

Whatever Style’s standing within the Post, Heard isn’t going to comment “about what factors into my decision.”