Where is the Martha Stewart we once loved?The funny, sharp, glamorous woman who never took herself too seriously seems to have been replaced by someone increasingly cranky, entitled and downright unpleasant.Martha’s latest Halloween disaster is just the latest example of a mogul who appears to have lost touch with the very public who made her a star.On Saturday, the 85-year-old lifestyle mogul, worth an estimated $400 million, dressed up as a homeless person, complete with torn clothing, dirt smeared across her face and a sign reading, ‘I AM HUNGRY HELP ME!!’The photograph was posted alongside a promotion for her home goods line. ‘My QVC candles are perfect for Halloween!!!!!’ read the caption.The post was quickly deleted following online backlash and, initially, Stewart stretched credulity by defending the costume as an attempt to raise awareness about homelessness. The funny, sharp, glamorous woman who never took herself too seriously seems to have been replaced by someone increasingly cranky, entitled and downright unpleasantAs the criticism intensified, she issued a second apology, admitting her first response ‘didn’t go far enough’ and acknowledging that the get-up was ‘insensitive and not funny.’Fine. Mistakes are made. But for a woman whose life and career have been defined by her exquisite taste, this is alarming – even to those close to her.’The problem isn’t that the public misunderstood the joke,’ a source who worked with Stewart for seven years and remains friendly tells me. ‘The problem is that there wasn’t a funny joke to begin with.’Years ago, I met Stewart after I was invited to her Chelsea office to discuss a possible job. I had been doing media relations for the designer Kate Spade and Stewart had apparently liked my work.Fifteen minutes before she appeared at the meeting, her driver called to announce her imminent arrival. The office practically went into lockdown. It was like a scene from The Devil Wears Prada. Miranda Priestly was preparing to descend.I found it hysterical and so did she. That was the magic of Martha. She was quirky, larger than life and, yes, a bit dictatorial, but her staff seemed to absolutely adore her. She was in on the joke.’The old Martha could be terrifying, but there was always a twinkle in her eye. She knew she was a character and enjoyed playing that character. Now, it feels like the twinkle has disappeared. All we’re seeing is the attitude without the charm,’ the insider tells me.Stewart’s easiness was always a confection, of course. Without a prodigious work ethic and whip-sharp smarts, one cannot rise from a working-class upbringing to launch a catering business from their home and build it into a global media empire.She’s a badass. Not that it hasn’t gotten her into trouble.In 2004, Stewart was found guilty of conspiracy, obstruction and lying to investigators about her sale of stock in a biopharmaceutical company and an alleged insider trading scheme.’I’ll be back. I will be back,’ she said outside of the courthouse after sentencing. ‘I’m used to all kinds of hard work, as you know, and I’m not afraid. I’m not afraid whatsoever.’She served five months in prison, plus five months more of home confinement and two years of supervised probation. She settled the civil insider trading charges and paid a fine.When she walked out of the Federal Prison Camp in Alderson, West Virginia, in 2005, she wore a handmade yarn poncho made for her by a fellow inmate.Take that Securities and Exchange Commission!Where is that sense of humor today?The Halloween faux-pas didn’t happen in isolation.In August, Stewart seemed to fire a crumpet across the bow of the Duchess of Sussex.’If you’re an actress, it’s hard to then transition to a princess and then from a princess into a homemaking guru on a television show,’ Stewart told People magazine about Meghan Markle’s foray into the lifestyle genre. ‘It doesn’t sort of follow. So go from there.’Perhaps the perceived slight was unintentional. Even so, is that an excuse?Then there have been the increasingly thirsty photographs that she has posted to social media. Posing in a bathroom mirror in her lacy pajamas – decolletage bared. Pouting in the pool, by the bar, in the make-up chair. In Sports Illustrated’s swimsuit edition.Let me be clear: I have absolutely no problem with women looking sexy at 25, 55 or 85. No one should be told to cover up because of a birthday, but there’s a difference between confidence and what seem to be attention-seeking behaviors that are beneath a diva of her magnitude.It would be tragic for her to become a caricature. On Saturday, the 85-year-old lifestyle mogul, worth an estimated $400 million, dressed up as a homeless person’Nobody begrudges Martha wanting to look hot, she never had to work this hard to get noticed. She was fascinating without trying,’ an event source who has hosted Stewart several times told me.Her repeat appearances across season 16 of The Real Housewives of New York raise similar questions. The woman who once defined effortless sophistication now seems increasingly determined to chase every opportunity to stay in the spotlight.A 2024 Netflix documentary aired her claims about her ex-husband Andy Stewart’s alleged infidelity – and her own extra-marital diversions.’I don’t know how many different girlfriends he had… but I think there were quite a few… If you’re married and you think you’re happily married, and your husband starts to cheat on you, he’s a piece of sh*t. Look at him as a piece of sh*t and get out of it, get out of that marriage,’ she said.In a 2024 statement, Andy Stewart’s current wife (he and Martha divorced in 1990 and reportedly haven’t spoken since) said he had a ‘dark’ chapter of his life and called his marriage to Martha Stewart, ‘painful and abusive.’Off camera, the interviewer reminded Martha Stewart that she also had an affair, early in her marriage.’I had a very brief affair with a very attractive Irishman, and it was just nothing,’ she said. ‘It was nothing… I would have never broken up a marriage for it. It was nothing.’Look, Martha Stewart was never going to be a sweet older lady. She was never a sweet younger lady. But the saddest thing about watching an icon age isn’t watching them get older, it’s watching them lose the very qualities that made them iconic.You used to be in on the joke, Martha.These days, you’re beginning to look like the punchline.