Michelle and Barack Obama are no strangers to false facts about their lives hitting the rumor mill. This includes speculation that the former president wasn’t always faithful. One such story turned out to be complete nonsense, but an older one is more complicated. While the rumors that Barack had an affair with Jennifer Aniston are easily dismissible, the claims that he maintained a relationship with Sheila Miyoshi Jager in the early days of his relationship with Michelle are hard to assess.
The story dates back to the early ’90s, though it didn’t surface until decades later. Because it involves a non-public figure during a time when Barack wasn’t a public figure himself, it’s hard to know where the truth lies. The scenario surrounding the hearsay involving the “Friends” star is the opposite. Virtually no one bought the rumors — not even InTouch Weekly, which first ran the story. But while denying the relationship was romantic, insiders insisted that the two had gotten pretty close.
“Michelle knows theyʼre chummy, and apparently sheʼs not thrilled,” a source told InTouch Weekly in August 2024, according to (via PopCulture). Aniston’s response to the Barack affair rumors was priceless. “Oh, s**t,” she laughed when the “Jimmy Kimmel Live” host showed the magazine cover. “Of all the calls you get from your publicist, where you’re just like, ‘Oh, no, what’s it gonna be?’ … and then it’s that.” Aniston couldn’t fake her reaction despite her acting chops. Jager, on the other hand, reacted quite differently.
Barack Obama’s ex-girlfriend claims he cheated on Michelle Obama
In 2017, Sheila Miyoshi Jager, a woman Barack Obama almost married before Michelle Obama, contended the two rekindled their romance in 1990. By then, Barack and Michelle’s relationship was already serious, with the two tying the knot two years later. “I always felt bad about it,” she told David Garrow in “Rising Star: The Making of Barack Obama” (via People). According to Jager, she and Barack remained involved until 1991. His first date with Michelle was in 1988.
Barack and Jager broke up in 1987, the year she moved to South Korea. They re-established contact when she returned to the U.S. and applied for a fellowship at Harvard University, a decision partly motivated by the fact her ex was studying law there. According to Jager’s version of events, their relationship ended for good when she found someone else, suggesting Barack would have continued his involvement with Jager while seeing Michelle. “As much as I loved him, I was relieved when our paths finally parted,” she told Garrow.
Barack never addressed Jager’s claims. He has also downplayed the relationship. In his 1995 memoir, “Dreams From My Father,” he mentioned his life with Jager — even citing their letters — without ever naming her. “Very sweet lady, as busy as I am, and so temperamentally well-suited,” he wrote, further describing their relationship as based on mutual interest (via Time). “It is nice to have someone to come home to after a late night’s work. Compromises, compromises.”
