Michelle Obama's Brother Thought Barack Was Just a Fling

Michelle Obama 2013 official portrait. Official White House photo by Chuck Kennedy. Public domain.

When Michelle Obama started dating a guy named Barack, her brother Craig Robinson didn't expect it to last. In fact, he figured the relationship would be over in about a month. More than 32 years of marriage, two daughters, and one historic presidency later, it's safe to say Robinson's prediction was dead wrong. But his candid admission on a recent podcast with Michelle didn't just provide laughs — it reignited public curiosity around the Obamas' marriage, both past and present.

The Early Doubts

Robinson didn't hold back on the first episode of their new podcast "IMO." When his little sister first started dating Barack Obama, he didn't think the relationship was going to last long. According to Craig, the family hadn't heard of him and were skeptical about the man with the unusual name. He compared the situation to Michelle's previous relationships, which he recalled as being short-lived.

"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?'" Robinson said. "And I’m thinking to myself, it's gonna last like about a month like most of your relationships did," as reported by PEOPLE.

Michelle disagreed with that take, insisting that she had a history of long-term relationships. But Robinson pushed back, stating he couldn't remember any that lasted longer than a month — reinforcing just how little faith he had in Barack in the beginning.

First Impressions Matter

Michelle's brother wasn't alone in his cautious approach. When Barack first met their mother, Miriam Robinson, her reaction was reserved. She noticed his height — a positive for the 5'11" Michelle — but that was about it. Craig echoed that sentiment, sharing that while his mom noted Barack was tall, he still didn't think the relationship would go anywhere.

The Basketball Test

Craig's outlook shifted after a casual game of pickup basketball. Following advice from their father — that a person's character shows on the court — Craig decided to see what Barack was made of. He admitted the future president couldn't go right due to being left-handed, but what stood out was how well he played with others and blended in with the group. It was that experience that convinced Craig that Barack might be more than just a fling.

Marriage, Kids — And Constant Scrutiny

Barack and Michelle married in October 1992 and had two daughters: Malia, now 26, and Sasha, 23.

Despite their longevity, public speculation about the health of their marriage hasn't gone away. Earlier this year, rumors about a potential split ramped up when Michelle was noticeably absent from former President Jimmy Carter's funeral, which Barack attended alone. Around the same time, Michelle also declined to join Barack in attending Donald Trump's second inauguration, further fueling gossip about trouble in their relationship.

Michelle addressed the chatter on the "Work in Progress" podcast, hosted by Sophia Bush. She discussed how society often struggles with women exercising independence. She explained, "That's the thing that we as women 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," as reported by PEOPLE.

Still Going Strong — Publicly and Privately

Despite public speculation and Craig's early doubts, the Obamas continue to present a united front. On Valentine's Day this year, Barack posted a tribute to Michelle on social media, celebrating their 32 years together and expressing his continued admiration for her.

Craig Robinson's one-month prediction turned out to be wildly off base. But his skepticism offers a unique lens into the ordinary beginnings of one of America's most famous couples. Before the campaign trails and international headlines, they were just two people trying to figure it out — and one older brother thinking it wouldn't last past the calendar page.

References: Michelle Obama's Brother Craig Robinson Thought She and Barack Obama Would Last 'About a Month' | Why Michelle Obama's Brother Thought She and Barack Would Last 'About a Month'