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.