Michelle Obama’s Brother Didn’t Think Her Relationship With Barack Would Last
Michelle Obama’s brother, Craig Robinson, has revealed that he initially didn’t believe his sister’s relationship with Barack Obama would last more than a month.
Speaking on the latest episode of The Light Podcast with Michelle Obama—in a segment focused on dating and featuring actress Tracee Ellis Ross—Robinson reflected on his early impressions of the future president when the two first met. The episode comes amid renewed speculation about the Obamas’ marriage, following Michelle’s absence from several recent high-profile events, including the funeral of President Jimmy Carter and former President Donald Trump’s inauguration, both of which her husband attended alone.
“I love talking about dating, because I haven’t done it in decades,” Michelle said at the start of the episode, according to DailyMail.com.
Robinson, known for his candid sense of humor, said he learned from their father that a person’s character can often be judged by how they play pickup basketball—an insight that led Michelle to ask him to test Barack on the court.
“And I’ve told this story many times about when you first started dating Barack,” Robinson recalled. “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.”
Michelle quickly objected, saying, “That’s not true. I’ve had many a long-term boyfriend.”
Her brother laughed and replied, “I wouldn’t call those guys boyfriends.”
Robinson also recounted his first impression of Barack when they met, noting that their late mother, Marian Robinson, was delighted by his height. “And I said to myself, ‘Too bad it’s not going to last,’” he joked.
Eventually, Michelle asked him to take Barack to play basketball—a test Robinson initially resisted.
“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 it,’” Robinson said.
He eventually agreed, adding, “Obviously, we had a great time playing. He did fine.”
Marriage Rumors and Public Speculation
The Obamas’ marriage has been the subject of persistent speculation in recent months, despite both Barack and Michelle addressing the state of their relationship publicly.
In a recent conversation with Hamilton College President Steven Tepper, former President Barack Obama offered an unusually candid reflection on his marriage.
“I was in a deep deficit with my wife,” he said. “So I have been trying to dig myself out of that hole by doing occasionally fun things.”
Barack has previously acknowledged that his years in office placed strain on their relationship, telling interviewers that their time away from the White House has helped them reconnect.
“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 told CBS Mornings in May 2023, calling Michelle “forgiving” and praising her strength throughout his presidency.
Michelle’s Response: Choosing Herself, Not Separation
For her part, Michelle Obama has been outspoken about her recent decisions to step back from certain public commitments, clarifying that those choices have nothing to do with marital discord.
Appearing on actress Sophia Bush’s Work in Progress podcast, the former first lady addressed rumors about her marriage, describing them as a reflection of society’s discomfort with women prioritizing themselves.
“That’s the thing that we as women struggle with—disappointing people,” Michelle said. “So much so that this year, people couldn’t even fathom that I was making a choice for myself. They had to assume that my husband and I are divorcing.”
“That this couldn’t be a grown woman just making a set of decisions for herself, right?” she added. “That’s what society does to us.”
She continued, emphasizing how women are often pressured to justify their personal choices when they deviate from public expectations.
“We start asking, ‘What am I doing? Who am I doing this for?’ And if it doesn’t fit into the stereotype of what people think we should do, then it gets labeled as something negative and horrible,” Michelle said.
Reflecting on her own evolution, she concluded:
“Now is the time for me to start asking myself these hard questions of who I truly want to be every day. And that looks like whatever I want it to look like.”
A Relationship Built on Mutual Respect
Despite the lighthearted teasing from her brother and ongoing public speculation, the Obamas continue to project mutual respect and affection—both acknowledging the challenges of decades in the public eye.
While Craig Robinson may have once doubted the longevity of his sister’s relationship with the man named “Barack,” history has proven him wrong. More than three decades later, the couple remains one of the most recognizable and influential partnerships in modern American life.