Michelle Obama’s older brother, Craig Robinson, has revealed he was initially skeptical about her relationship with former U.S. President Barack Obama, sharing his candid thoughts during a recent episode of their Michelle Obama: The Light Podcast.
Michelle and Barack first met in 1988 at a Chicago law firm, where Michelle was assigned as Barack’s mentor. Despite their professional beginnings, a romantic connection soon blossomed. The couple married in 1992 and went on to welcome two daughters — Malia in 1998 and Sasha (Natasha) in 2001.
In 2009, Barack made history as the first Black president of the United States, serving two terms until 2017. Over the years, both he and Michelle have openly acknowledged that the pressures of public life — particularly during their time in the White House — put a strain on their marriage.
Now, her brother Craig is shedding light on what he thought when Michelle first brought Barack into the picture. On the podcast episode that aired Wednesday (April 16), he recalled his early doubts.
“When Mich started dating Barack, we had no idea who he was. I remember thinking, ‘Barack? Who even has a name like that?’” Craig said, jokingly. “And I figured it would last maybe a month, like most of your relationships.”
Michelle, 60, playfully fired back at her 62-year-old brother’s jab: “That’s not true. I had many long-term boyfriends!”
Craig replied with a laugh: “I wouldn’t call those guys boyfriends.”
He also recalled how their mother reacted to meeting Barack for the first time. “Mom’s first comment was, ‘Well, at least he’s tall!’” he said. “Because Mich usually towered over her other boyfriends.”
Still, he admitted, “I said to myself, ‘Too bad it’s not going to last.’”
More than three decades later, their relationship has proven otherwise. Despite recent speculation about marital troubles, Michelle recently addressed the rumours head-on during an appearance on Sophia Bush’s Work in Progress podcast.
Since leaving her role as First Lady, Michelle said she’s finally able to make personal choices without public expectation — something she believes has been misinterpreted.
“When I say ‘no’ to things now, people usually respect it — and I’m okay with that,” she said. “But that’s something women often struggle with: disappointing others.”
Michelle reflected on the assumption that her independence must indicate problems in her marriage.
“People couldn’t fathom I was making decisions just for myself, so they assumed Barack and I were divorcing,” she said. “It couldn’t just be a grown woman choosing for herself, because that’s not the narrative society gives us.”
She added: “When our choices don’t align with people’s expectations, they’re often twisted into something negative or scandalous.”
Who knew that Michelle Obama’s family had such strong opinions about her relationship?
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