A few months ago, a Democratic source wrote to me with a clever story idea. I mostly write about the new generation of Silicon Valley wealth—people in their 30s and 40s who made their fortune in Web 2.0 or now 3.0, and how they are deploying their money into politics and philanthropy. But maybe these newbies could learn something meaningful from an old hand with more influence than any of them, a truly seminal figure from Web 1.0 who seems, on paper at least, to be a king of Washington.

My source was thinking of Steve Case, the AOL co-founder who is uber-connected across Silicon Valley and D.C. To wit: Two of Case’s closest colleagues at his venture capital firm, Revolution, were none other than Ron Klain, now the White House chief of staff, and J.D. Vance, who helped refine Case’s investment thesis across the heartland after publishing Hillbilly Elegy and is now a likely U.S. Senator. Yes, that’s an odd couple, but they together serve as a reminder that Case somehow always finds himself in the middle of the zeitgeist.