Obama biographer on letters to 44's ex he hopes the public never sees, how Michelle changed since Chicago days

EXCLUSIVE – Biographer David Garrow said former President Barack Obama once told him he hoped he would never read the letters penned to his former girlfriend, Sheila Miyoshi Jager, the woman he once hoped to marry before he met his future wife Michelle.

"Barack made it clear to me that he hoped I would never read them, I can put it that way. I think if the letters to Sheila ever become public, I think that will be a signal event," Garrow told Fox News Digital. "Those letters would detail just how extremely serious and extremely intense a relationship that was and that it continued off and on into his Harvard Law School years."

Garrow authored the lengthy 2017 biography "Rising Star: The Making of Barack Obama" and had several off-the-record conversations up into 2016 with the former president. He stunned social media last week with a lengthy Tablet magazine interview in which he made a series of eyebrow-raising claims about Obama from his work documenting his formative years. The 16,000-plus word interview featured an assortment of news-making comments, touching on everything from his allegation that Obama's first memoir was fictionalized to details about fantasies he confessed in a letter to a former girlfriend about having sex with men.

Garrow stands out in the pantheon of people who've profiled Obama – while many journalists have been dazzled by the 44th president, Garrow called his memoir "Dreams From My Father" essentially fictionalized, said he was too lazy to be a good Supreme Court justice, and said his presidency will be considered a failure in the long run because of its foreign policy shortcomings. If he sounds like an abrasive right-wing figure, he isn't – he calls himself to the left of Obama on issues like health care, is avowedly pro-choice and lamented Obama hadn't modeled his post-presidency after Jimmy Carter, whose humanitarianism has often received better reviews than his one-term stint in the White House.

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David Garrow, who wrote the lengthy 2017 biography "Rising Star: The Making of Barack Obama," stunned social media with claims about the former president from his observations and interviews. (Screenshot/YouTube)

Obama's relationship with Jager (prononced YAY-ger) was dissected in the lengthy "Rising Star" and the two differed on what broke them up. Obama said in his own memoir their relationship ended as he embraced his Black racial consciousness – he is biracial – while Jager told Garrow that it was an argument about him not sufficiently in her view condemning an incident of antisemitism.

Garrow's dissection of Obama's relationships in the book and the suggestion his courtship of Michelle Robinson was politically calculated to win favor with Chicago's Black political community drew sharp criticism from some media observers in 2017. 

"The characterization of their romance as a lukewarm, politically advantageous union is plainly out-of-touch and offensive", one Time writer sniffed.

Garrow told Fox News Digital the Obama marriage is genuine and loving, but it wasn't wrong to say that there a mixed-race marriage could have made life difficult for Obama at the time. Married in 1992, he later was elected to the Illinois State Senate in 1996 and, after an ill-fated congressional bid in 2000, was elected to the U.S. Senate from Illinois in 2004. 

"The one aspect that I will endorse or that is inescapably true is that by 1988, he knew he wanted to run for public office in Chicago," Garrow said. "And he knew… that having a wife like Sheila Jager, half-Dutch, half Japanese, would not cut it in Black Chicago… Having a non-Black spouse 25, 35 years ago was an active political problem for a Black candidate."

The Pulitzer Prize-winning Garrow spoke with several of Obama’s former girlfriends for his biography, but was never given access to Michelle Obama for the project. However, he spoke to enough people close to her to say that the former first lady has evolved over the years. The Obamas, who have become enormously wealthy thanks to lucrative book deals and speaking engagements, have accumulated a wide variety of celebrity friends.

"There's no resemblance between their lives today and who they were 20 years ago. And when I was doing most of my interviewing across Black Chicago in like 2010, 2011, 2012, even then, folks could see this sort of 'desire to hang with celebrities' theme building in the White House," Garrow said. 

"Some of the folks weren't surprised that Barack was going that way, but they were really painfully upset that Michelle had seemingly lost her grounding because they viewed her as just the epitome of a hardworking, working-class South Side Chicago Black family," he continued. "Granted, he's this, you know, multi-cultural, multiracial creature from another planet. But they couldn't fathom that Michelle, you know, no longer was who she was." 

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Chicago residents who once knew her were stunned at Michelle Obama’s lifestyle pivot as she and her husband became extremely wealthy, according to Obama biographer David Garrow. (CBS/Screenshot)

As for Obama’s previous partners, Garrow generated headlines when he explained details of a letter the former president penned decades ago to Alex McNear, a different former girlfriend from Obama’s time at Occidental College. Garrow told Tablet that McNear showed him love letters written by Obama, but one paragraph was redacted. 

He wondered what was so sensitive that it was redacted, but by the time the paperback version of "Rising Star" was released, Garrow was able to include the forbidden tidbit. 

"Alex sold those letters to Emory [University]. Alex had let me read all of the letters except this one paragraph that she redacted and just said, ‘It's about homosexuality,’" Garrow said. "So, I had one of my oldest friends, Harvey Klehr, who has been a professor at Emory his whole life. I had Harvey go to the Emory archives and Harvey copied out the missing paragraph by hand, pencil and paper." 

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The Tablet interview noted that "Barack writes to Alex about how he repeatedly fantasizes about making love to men," which appears in the paperback version of the biography but hardly registered as national news when the detail emerged. 

Garrow doesn't see a scandal there.

"I'm a historian, not a psychotherapist, but, you know, I'm 70 years old. My sense of the world is that, you know, a large majority of humanity has fantasy lives," Garrow said. "So, I don't I don't find that passage in any way scandalous. It's sort of representative of humanity."

Garrow said what was problematic in his view about Obama was how he changed after his failed 2000 bid to unseat Democrat Bobby Rush from the U.S. House of Representatives, going from a skilled Springfield legislator who could reach across the aisle to a hard-boiled partisan who gave Republicans a cold shoulder in office and deepened U.S. political divides. Then again, the feeling was mutual, as Senate Minority Leader Mitch McConnell famously said his top goal was to make Obama a one-term president.

 Former U.S. President Barack Obama listens as former first lady Michelle Obama delivers remarks during a ceremony to unveil their official White House portraits at the White House on September 7, 2022 in Washington, DC (Photo by Kevin Dietsch/Getty Images)

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So why did Garrow say that Obama was as "insecure" as former President Trump, the man who replaced him and the famously pugnacious leader of the opposing party?

"He does need to think of himself as victorious, successful," Garrow said. "This is perhaps the central aspect of his political personality that people have to appreciate. There's an inability to accept loss, accept defeat."

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