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It did figure that Havrilesky would fall into philosophical wheel-spinning about "winners" and "losers." Especially when her column is always about "winners" (only her) and "losers" (all the rest of us). It would be more essential to consider who defines "winning" and whether you should accept that definition, but something that complex would make her poor Tiffany earrings smoke.
For example, the characters of "Lost" are losers because they are allowing life to happen to them, instead of advancing upon it. Why did "The Others" (who I assume are resident agents of Dr. Fu Manchu, the guy who runs the Hansa Foundation) manage to capture the doctor and manipulate him like a Rush Limbaugh dittohead? Because he refused to recognize the enemy and to do anything effective against them.
For instance, he assaulted the "Other" broad a few episodes ago, and almost made it out of the prison. His first major mistake was leaving her alive. His second was trying to close the hatch against the "inrush of ocean water." If it really was the ocean, he would never be able to close that hatch unless he was born on Krypton. Since it wasn't really the ocean, he could have swum out against the "current" (which I expect was just a fire hose) and gotten away from the bastards. But no, he closed the hatch, and allowed the still-living bimbo to throw him back into prison. Patrick McGoohan, a much smarter Prisoner, would have thrown up all over him.
In reality...the one where "Lost" is a TV show stumbling to cancellation...the reason the characters are losers lies with the producer and writers. They don't want the show to end. They don't have any direction for the series. They are improvising on the spot, when they should have improvised and worked out the story of the series years before they shot the pilot. So they must keep raising dilemmas, and they must force their characters to lose, to postpone thinking up the next dilemma...which would take them one step closer to cancellation.
In "Twin Peaks," David Lynch revealed his only real talent was jerking around his audience. That audience liked it at first, but then they began to get queasy, and figured out that being jerked was...well, jerky. J.J. Abrams is about to see his audience turn against his choking, pointless pulls on their leashes, too. And I'll bet, like Lynch, he'll make a snotty "follow-up movie" to "Lost" that will curse the viewers of the TV show for abandoning him.
For the poster who wanted term limits for writers on shows, well, the esteemed Paul Dini only lasted the first season. He has good ideas and can implement them over the long term. (He created Harley Quinn, the Joker's girlfriend, and made her a long-time and complex character in the DC Comics universe. He also shows great ingenuity with his personal projects like "Jingle Belle," Santa's punk-rock daughter.) That's not the real problem with series writing.
An episode writer is generally only responsible for one episode. It's the person who coordinates the show - often called the story editor, if not the creator of the series - who navigates the overall direction of a show. Or who determines if a show has a direction at all.
The British TV people often praise here (who haven't watched much of it - they see only the best British shows, not the whole output which has as many losers as America has) owe much of their quality to strong story editors. They know what surprises and seismic shifts the show will have, when they will hit, and keep the episode writers on that track. That kind of control is exactly what "Lost" lacks, and what "Babylon 5" had.
But too often, being a celebrity and having fame distracts Hollywood producers from doing the groundwork they're supposed to do. It's so much more fun to have dinner at Morton's, with fanboyish and easily deluded journalists like Heather Havrilesky, than to sit your butt in the chair and home and work on your show.
To paraphrase a joke of the American wit, Henry Morgan: "Episodes of 'Lost' are rolling off the assembly lines. If they could keep them ON the assembly lines, they'd have a better show."