When I talk to progressive fundraisers, I often ask them to posit their dream principal, or white whale—someone whose fortune they would love to direct toward their own philanthropic or political ends. There are revealing answers, like Stripe co-founder Patrick Collison, and obvious ones, like MacKenzie Scott. But the question can actually become more elucidating when it is inverted: Who is the figure whose wealth they want to avoid?

The world of philanthropy and political donations, after all, is often rather risk-averse. Advisors, who make big bets with other peoples’ money, are highly attuned to the possibility that a particularly controversial ultra-high-net-worth donor could alienate their peers or taint an organization. The one name that has come up more than any other in these conversations is Sheryl Sandberg.

That is why I found it hard to not marvel last week as I read Sandberg’s announcement that she plans to dedicate more of her time to philanthropy after stepping down as Facebook’s first and only chief operating officer. Sandberg once had unimpeachable bonafides in the Democratic establishment: Larry Summers protégé, Obama-era feminist icon, presumptive Clinton cabinet member. She was reportedly ready to leave Facebook for Washington, in 2016, had the election gone the other way. Instead Sandberg became an avatar of Facebook’s work with the Trump campaign, and an increasingly toxic personage for the left as she managed the company through scandal after scandal. Democratic leaders, including Clinton, turned on Facebook and on Sandberg. Liberal politicians began to talk about Silicon Valley as if it were Big Oil or Big Tobacco. In what I thought was an era-defining moment, Elizabeth Warren, for one, announced that she would not take any money from Big Tech executives, just like she wouldn’t accept support from leaders at fossil-fuel companies.