Michelle Obama's Brother Was Never Convinced Her Romance With Barack Would Last

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Long before he was president, Barack Obama was working to become a lawyer and make a good impression on Michelle Obama and her family. In 1989, Barack poured a lot of energy into convincing Michelle to date him. She'd made the decision to pause her dating life, and, even after Barack changed her mind, Michelle's brother, Craig Robinson, was skeptical about their romance. "I'm thinking to myself, it's going to last for about a month like most of your relationships," Craig explained on his joint podcast with Michelle, "IMO." Michelle disagreed with her sibling, noting that she had other long-term boyfriends before she and Barack met.

When their parents, Fraser and Marian Robinson, met Barack, they came to the same conclusion as Craig. Although Barack's conversational skills charmed them, considering Michelle's dating history, Marian and Fraser agreed that the relationship wouldn't last. The family even started speculating on when the breakup would happen.

However, Craig later had the opportunity to weigh in on the relationship when Michelle persuaded him to play basketball with Barack. "She must have just absorbed the notion that Dad and I embraced that you can tell a man's character through a game of basketball," Craig wrote in his memoir, "A Game of Character." On their podcast, Craig admitted that he had been reluctant. "I am not doing your dirty work for you," he recalled informing his sister. "If he turns out to be a bad dude, I am not going to be the one to say."

Michelle Obama's first impressions of Barack Obama were mixed. Barack was working as an intern at the law practice where she worked, and his lack of punctuality annoyed her from the start. Decades later, Michelle was still griping about Barack's relaxed attitude toward timeliness in her 2025 podcast with Craig Robinson, "IMO." While Barack did capture Michelle's interest as they talked and shared a meal his first day, another unfortunate habit damaged his efforts. "Barack lit a cigarette, which would have been enough to snuff any interest," Michelle recalled in "Becoming." Marian and Fraser Robinson smoked during Michelle's childhood, and she and Craig made a valiant effort to get them to quit.

By the time Craig and Barack played that crucial game of basketball, Michelle had worked past her initial hang-ups. Despite Craig's reservations about the scheme, he wanted to help Barack. "I was so happy that she really liked this guy," Craig recalled in "A Game of Character."

When it came to judging Barack's skills on the court, Craig had a discerning eye: he was a top college player and he later became a coach. He was pleased to see Barack worked well with his teammates and owned up to his mistakes. "He's very confident without being cocky," Craig recalled telling Michelle in his memoir. He and his sister have a tight relationship, and Craig later realized providing his insights about Barack was important to their sibling bond. It also provided him with a chance to get to know his future brother-in-law better.