Back in December, AdFreak wrote about Brand Martha’s hoosegow metamorphosis from one more ruthless corporate titan to put-upon inmate. Just after midnight last night, Stewart emerged from her beige jumpsuit cocoon 20 pounds slimmer with a TV deal in her Birkin handbag and a fistful of flattering news profiles awaiting her at work. The Wall Street Journal yesterday published a story that makes her sound like the second coming of Eleanor Roosevelt to Alderson State Prison (if you have a sub and missed reading the story, click here). As told to the reporter by one of Stewart’s fellow cons, the humbled executive made nice with her neighbors, led yoga classes and business seminars and tried to arrange for a reunion between two estranged sisters. Newsweek’s cover story cites the same anecdotes and throws in a helping of toilet cleaning. It almost makes her seem… nice.

But is primetime America ready for a “nice” Martha? Strong. Surely! Humbled? No doubt. But part of the public’s fascination with Martha has been—to put it nicely— her gumption. And, for anyone who watched Cybil Shepherd’s deliciously overwrought portrayal of Stewart as a knife-wielding control freak, that was part of the fantasy. Now on board with Mark Burnett for an Apprentice spinoff, Stewart will have to walk a fine line between the Omnimedia maven we loved to loathe and the consoling cellmate now out on parole. Chances are she’s been that person all along. Still, no one is interested in Donald Trump’s softer side. His success as a media persona has hinged on the fact that he is at once part of, and the butt of, the joke. He knows it's his caricature that sells—the onion-loaf pompadour, the trademarked phrases, the egomania. Caricatures don’t walk fine lines. If Martha’s show is to succeed, she’ll have to find an image, stick with it and not look back.

—Posted by Deanna Zammit