Michelle Obama’s Brother Didn’t Think Relationship With Barack Would Last

In a recent episode of the IMO podcast, Michelle Obama's brother, Craig Robinson, shared a surprising admission: he didn’t think her relationship with Barack Obama would last longer than a month.

This particular episode, centered around the theme of dating and featuring actress Tracee Ellis Ross, aired amid renewed speculation about the Obamas’ marriage. Talk of a possible split has gained traction, especially following Michelle’s decision not to attend President Jimmy Carter’s funeral or accompany Barack to Donald Trump’s inauguration.

“I love talking about dating, because I haven’t done it in decades,” the former first lady remarked at the beginning of the episode, as cited by DailyMail.com.

Robinson noted that their father taught him early on that “you can really tell a person’s character by how they play pick-up basketball,” which led Michelle to ask Craig to put Barack through a casual “test” on the court during the early days of their relationship.

“And I’ve told this story many times about when you first started dating Barack. 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?’ And I’m thinking it’s gonna last a month like most of your relationships,” Craig recounted.

Michelle quickly pushed back on that claim: “That’s not true. I’ve had many a long-term boyfriend.”

Craig joked in response, “I wouldn’t call those guys boyfriends.”

He also recalled how their late mother, Marian Robinson, was impressed with Barack’s height during their initial meeting. “And I said to myself, ‘Too bad it’s not going to last,’” he remembered.

Craig continued, “But the best part of it was, after we met him and she had been dating him for a little while she said, ‘Would you mind Craig, taking him to play?’ And at first I said, ‘No way, I’m not going to do your dirty work for you. If he turns out to be a bad dude, I’m not going to be the one to say.’”

Ultimately, Barack held his own during the basketball session. “Obviously, we had a great time playing,” Craig said.

Still, rumors about trouble in the Obamas’ marriage have persisted. Barack Obama recently made an unusually honest comment about his relationship with Michelle during a talk with Hamilton College President Steven Tepper.

“I was in a deep deficit with my wife,” he admitted. “So I have been trying to dig myself out of that hole by doing occasionally fun things.”

He has acknowledged before that his presidency took a toll on their relationship during his time in office from 2009 to 2017.

“Let me just say this: It sure helps to be out of the White House and to have a little more time with her,” Barack said during a May 2023 interview, noting that Michelle has been “forgiving” of his faults.

For her part, Michelle recently addressed the rumors surrounding their marriage and clarified that her personal decisions aren’t reflective of any marital issues.

In a conversation on Work in Progress with Sophia Bush, she opened up about why she’s taken a step back from the spotlight, explaining that these were intentional choices for her own well-being—not signs of relationship problems.

“That’s the thing that we as women, I think we struggle with disappointing people. I mean, so much so that this year people were, you know, they couldn’t even fathom that I was making a choice for myself that they had to assume that my husband and I are divorcing,” she explained.

“That this couldn’t be a grown woman just making a set of decisions for herself, right?” Michelle continued, adding, “That’s what society does to us.”

She went on to describe how women often feel compelled to justify their choices if they deviate from societal expectations.

“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,” she said.

Reflecting on her current mindset, she concluded, “So you know, now is the time for me to start asking myself these hard questions of who do I truly want to be every day.” That, she emphasized, “looks like whatever I want it to look like.”