Donald Trump & Martha Stewart Look Awfully Cozy In Photos Taken Before He Became President
Donald Trump and Martha Stewart have a lengthy and complicated connection. Back in 2006, the contentious side of their relationship came to the forefront when Trump and Stewart were involved in a feud involving their respective versions of "The Apprentice." When Stewart's iteration didn't last, Trump insulted her skills as a TV personality. In an even lower blow, Trump also brought up Stewart's insider trading scandal – less than a year after she'd been incarcerated. "The letter is so mean-spirited and reckless that I almost can't believe my longtime friend Donald Trump wrote it," Stewart replied at the time (via CBS News).
Photo evidence supports Stewart and Trump's chummy bond. When they met up at a book party in the early 2000s, they were all smiles as they stood close together for a photo op. They also displayed friendly camaraderie as they posed for a promo photo ahead of their competing reality shows, with Stewart adjusting Trump's signature red tie.
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Stewart seemed to forgive Trump's outburst eventually, since the pair appeared happy once again in a 2014 photo. A year earlier, Trump turned on the compliments when Stewart hit the online dating scene. "She looks terrific, better than ever, any guy would be lucky to be with her," Trump posted on X, formerly Twitter. Although Stewart has admitted she's not looking for serious romance, it's possible that Trump's praise reinstated him into her circle of friends.
Trump's political career made his connection with Stewart even messier
Given Donald Trump and Martha Stewart's sometimes fraught past, it's not a surprise that his presidential aspirations added a whole other layer of difficulty to their relationship, ending their formerly cozy connection. They started moving further apart when Stewart declared herself a Hillary Clinton supporter in 2016. At the time, the media mogul twisted the knife even further by insulting Trump's qualifications. "There is so much to know and so much to learn and so much diplomacy and kindness and introspection that goes with that kind of job," Stewart explained to CNNMoney in September 2016 (via People). "And it does not exist in the world of Donald Trump."
After Trump was victorious, Stewart sent him her well-wishes. However, it's unclear where their friendship stood after that, since Stewart still couldn't stop throwing shade on his lack of political expertise. Four years later, Stewart decided business interests trumped personal feelings. Rather than risk alienating supporters of her media empire, she kept her opinions to herself. By 2024, the pendulum moved again, and Stewart was clear that Trump still hadn't earned her vote.
Regardless of their past friendship, Stewart's also demonstrated that family ties are her top priority. In January 2026, Jude Stewart, Stewart's granddaughter, motivated the lifestyle icon to use her platform to criticize Trump's immigration policies. While the action may not have endeared her to Trump, Stewart's decision sparked praise from her social media followers.