Happy Monday morning from San Francisco.

Thanks for subscribing to Puck. Today, I’m writing you with some exclusive news: Jeff Bezos is making a $100 million to the foundation of none other than Barack Obama. It’s a somewhat surprising move, given the historical non-relationship between the two men, but one that makes perfect sense in the context of Bezos’ post-Amazon evolution from feared chief executive to a regular on the gala circuit.

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Bezos and Obama’s Surprise $100 Million Marriage

A nine-figure gift from Jeff Bezos to the Obama Foundation, midwifed by Jay Carney, marks another evolution in Bezos’ remarkable career as the Amazon founder seeks new causes (and friends) in politics and philanthropy.

As tightly as Barack Obama embraced Silicon Valley during his two terms in the White House, Amazon billionaire Jeff Bezos was never invited to the schmooze-fest. The two spent years in close proximity: Bezos moved into a spacious Kalorama mansion, just off Embassy Row, a few years after purchasing The Washington Post in 2013. But with the exception of a single C.E.O. luncheon they both attended in late 2009, I haven’t found any reporting, and zero photographs, of Obama and Bezos even in the same room.

That’s why I was somewhat surprised to learn that Bezos recently committed a whopping $100 million to the Barack Obama Foundation. The donation has been whispered about in politics and philanthropy circles over the last few months, and the Obama Foundation confirmed the news when I reached out last week. I’m told the $100 million was midwifed by Jay Carney, Bezos’ political sherpa and the former Obama press secretary. Carney ran point for Bezos, and Obama eventually spoke directly with the Amazon C.E.O. earlier this year. The two are not close, but “have seen each other socially from time to time,” Valerie Jarrett, the Obama family’s longtime aide-de-camp told me. 

The gift, the largest single donation ever made to the Foundation, has no restrictions on its use. But it is very common, and increasingly controversial, for major donors to be granted some naming honor in return for a donation of that size, be it a Sackler wing of The Louvre or a Koch theater at Lincoln Center. In this instance, though, Bezos asked for the public plaza near the center to be named the John Lewis Plaza, after the late congressman and civil rights icon—part of an intentional strategy, the foundation said, to “change the paradigm around naming.” Jarrett said she hopes the donation will trigger a new type of naming tradition in philanthropy, one where they don’t just honor the rich and powerful; other finalized named gifts to the Foundation will be announced soon and follow a similar playbook. “We are hoping that other institutions might adopt this strategy as well,” she said.

Bezos’ gift is in the staid, bipartisan tradition of mega donors, celebrities, and corporations seeking adjacency to the good works and mythmaking of post-presidential life. The main work of the Obama Foundation, after all, is the construction and administration of a presidential library. Obama in September broke ground on what they are calling a “presidential center”—not technically a library—on Chicago’s South Side. The Obama Foundation also runs other programming, such as a fellowship program to promote rising leaders across the country, which the Bezos gift will help bring to greater scale. Financial participation in these projects offers not just a flattering glow, but also some access to other high net worth individuals, and, of course, to the former president himself. 

Unlike a presidential campaign, however, there are no legal constraints on the size of the checks that can be cashed—and no law preventing a president from soliciting contributions before their term in office is over. As a result, presidential libraries tend to rake in big money very easily, not just from longtime friends, but also newfound ones, like Bezos, who emerge from concentric circles of associates and seek partnership. The Obama Foundation, for instance, has already raised over $720 million from donors toward its $1.6 billion goal, including about $170 million in 2020 and $140 million in 2019, according to recent tax filings. Cumulatively, some of its biggest donors in the past include Silicon Valley personalities, like Bill and Melinda Gates ($50 million), John Doerr and Sean Parker; the latter two also served on the Obama Foundation’s board. Bezos’ ex-wife, MacKenzie Scott, last year also said she had contributed an undisclosed amount. But the Bezos gift is the first donation that is big enough to come with naming rights. “I’m thrilled to support President and Mrs. Obama and their Foundation in their mission to train and inspire tomorrow’s leaders,” Bezos said in the announcement. “I can’t think of a more fitting person to honor with this gift than John Lewis, a great American leader and a man of extraordinary decency and courage.”

Bezos’s $100 million donation follows an inflection point in his career. Despite hiring former Obama aides like Carney, Bezos is despised by what Carney might call the professional left, given his unapologetic business practices, stratospheric net worth, and essentially libertarian politics. Since stepping down as the C.E.O. of Amazon last year, however, he has been hunting for philanthropic projects that would, intentionally or not, also soften his reputational edge and forge inroads for a wider circle of friends. Like the Obamas, who signed production deals with Netflix and Spotify, Bezos has been increasingly preoccupied with the overlapping worlds of activism and entertainment after stepping back from Amazon last year. A hefty donation to the former president’s foundation thus greases Bezos’ entry into Obama-world, and to the Democratic establishment more broadly. Emeritus status in the American elite means both men are now free to rub shoulders without the whiff of scandal. 

An enormous gift to the Obama Foundation is also perfectly on brand for Bezos’ post-Amazon pivot to elder statesman. Until late in life, Bezos had a fairly measly record in the world of charity. But public scrutiny of the world’s second wealthiest man has increased exponentially alongside his net worth. (Even last week, a $500,000 grant he made at a charity gala in West Hollywood was greeted with groans.) In 2018, shortly after being christened the world’s wealthiest person for the first time, he unveiled two $1 billion commitments, for a network of preschools and a network of nonprofits working on homelessness. Less than two years later, Bezos unveiled a $10 billion pledge that he calls the Bezos Earth Fund, money that he will dole out in grants to climate nonprofits over the next decade. Since stepping down as C.E.O., Bezos has spent more of his time on charity—he and his girlfriend, Lauren Sanchez, were all over the COP climate conference in Scotland this month, taking meetings—and with about $200 billion to give away, he’s got plenty of opportunities.

For now, Bezos seems to be gravitating toward broadly popular (some might say bland) nonprofits. He also seems particularly enamored of nice, round numbers, dispersing many of his high-profile gifts in increments of $100 million. That’s the size of the checks he’s written recently to big climate groups like the Nature Conservancy and the World Resources Institute, and to Jose Andrés and Van Jones for whatever they’d like, as part of his post-spaceflight P.R. blitz. The only bigger single gift he has made is the $200 million he promised to another political institution, the Smithsonian, this summer. Each of those gifts, like his donation to the Obama Foundation, seem to reflect a calculated ambition to go big while playing it safe. Allying with a popular former president? An easy winner. 

For Bezos, more important than what the professional left thinks of him is how history thinks of him. Carnegie and Rockefeller, after all, were reviled at the times of their deaths, but the libraries and foundations that bear their name have recast the first Gilded Age as an era of progress and generosity. Their tech industry successors want to do things differently—and indeed they are—but today’s legacies are forged just the same way.

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