Michelle’s Brother Didn’t Think Relationship With Barack Would Last
Michelle Obama’s brother, Craig Robinson, offered a candid glimpse into the early days of his sister’s relationship with former President Barack Obama—admitting he didn’t think it would last more than a month. The revelation came during a new episode of their IMO podcast, which centered on dating and featured actress Tracee Ellis Ross.
The light-hearted discussion arrives at a time when renewed speculation about the Obamas’ marriage has dominated headlines. Rumors escalated after Michelle chose not to attend President Jimmy Carter’s funeral or join Barack at President Donald Trump’s inauguration—an absence many interpreted as signaling deeper personal issues.
“I love talking about dating, because I haven’t done it in decades,” Michelle remarked during the episode.
Robinson recounted how their father taught him that a man's character could be judged by how he handled himself on the basketball court. That lesson, he explained, became directly relevant when Michelle introduced him to a then-unknown young man named Barack.
“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,” Robinson joked.
Michelle pushed back immediately. “That’s not true. I’ve had many a long-term boyfriend.”
Robinson wasn’t convinced. Laughing, he shot back: “I wouldn’t call those guys boyfriends.”
He recalled his first impression of the future president—including his mother’s reaction. “And I said to myself, ‘Too bad it’s not going to last,’” Robinson said, noting that their mother, the late Marian Robinson, approved of Barack’s height.
Michelle, he added, even asked him to take Barack out for a test on the basketball court. Robinson initially refused. “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,’” he laughed.
“Obviously, we had a great time playing,” Robinson admitted—Barack held his own on the court.
A Marriage Under the Microscope
The humorous recollections contrast sharply with the ongoing swirl of reports about trouble in the Obamas’ marriage—rumors fueled by both Michelle’s absence from high-profile events and unusually direct comments from Barack himself.
In a recent conversation with Hamilton College President Steven Tepper, Barack admitted, “I was in a deep deficit with my wife. So I have been trying to dig myself out of that hole by doing occasionally fun things.”
The former president has acknowledged before that his marriage took a significant toll during his years in the White House.
“Let me just say this: It sure helps to be out of the White House and to have a little more time with her,” he said in a May 2023 interview, calling Michelle “forgiving” of his shortcomings.
Michelle, meanwhile, has pushed back against the growing speculation. During a conversation on Sophia Bush’s Work in Progress podcast, she argued that her recent decision to step away from certain public appearances had been misinterpreted.
“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,” Michelle said.
“That this couldn’t be a grown woman just making a set of decisions for herself, right?” she continued. “That’s what society does to us.”
She emphasized that women often feel compelled to justify their choices, especially when those choices break from public expectations.
For now, Michelle Obama continues to deny any claims of marital trouble—but as the public fascination grows, the Obamas find themselves once again in an unflattering spotlight they can’t quite escape.