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Michelle Obama’s older brother, Craig Robinson, admitted that he initially had doubts about her relationship with Barack Obama — and even thought it wouldn’t last more than a few weeks.
In the latest episode of the IMO podcast, which Craig co-hosts with his sister Michelle, he opened up about his first impressions of the man who would later become the 44th President of the United States.
“So Mich starts to date Barack, and we don’t know who this guy is, we’re just like, ‘Barack? Who’s got a name like Barack?’” Craig said on Wednesday’s episode. “And I’m thinking it’s gonna last a month like most of your relationships.”
Michelle quickly stepped in to defend her romantic track record. “That’s not true. I’ve had many a long-term boyfriend,” she said.
“I wouldn’t call those guys boyfriends,” Craig responded bluntly.
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Craig also recalled Barack’s first meeting with their mother, Miriam Robinson. “I remember mom’s first thing was, ‘Oh, at least he’s tall!’” he said. “That was her first thing she said, because Mich was usually posting up her other boyfriends.”
Despite the positive impression on their mom, Craig remained skeptical. “Too bad it’s not going to last,” he remembered thinking after the meeting.
Of course, the relationship did last. Michelle and Barack married in 1992 and went on to have two daughters — Malia, 26, and Sasha, 23.
In recent months, the Obamas faced renewed public speculation about the state of their marriage. In January, Barack attended the funeral of former President Jimmy Carter without Michelle. Days later, Michelle confirmed she would not be attending Donald Trump’s second presidential inauguration, fueling online rumors of marital trouble.
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Michelle addressed the speculation last week during her appearance on Sophia Bush’s Work in Progress podcast.
“The interesting thing is that, when I say ‘no,’ for the most part people are like, ‘I get it, and I’m OK,’” she said. “That’s the thing that we as women, I think we struggle with — disappointing people. I mean, so much so that this year people couldn’t even fathom that I was making a choice for myself that they had to assume that my husband and I are divorcing.”
“This couldn’t be a grown woman just making a set of decisions for herself, right?” she continued. “But that’s what society does to us. We start actually, finally going, ‘What am I doing? Who am I doing this for?’ And if it doesn’t fit into the sort of stereotype of what people think we should do, then it gets labeled as something negative and horrible.”
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Meanwhile, Barack offered a rare public reflection on their relationship while speaking at Hamilton College on April 3.
“I was in a deep deficit with my wife,” he said. “I’ve been trying to dig myself out of that hole by doing occasionally fun things.”
Despite the occasional bumps, the couple — now married for over three decades — continues to share their personal journey with candor, humor, and a few family anecdotes.
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