JB issued a statement: “I have nothing but love and respect for my cousin Jennifer. While we belong to different political parties, we share a deep respect for individual civil rights. I have and always will support her.”

Did he get her vote in the end? “She’d like to pass on this question,” says a communications aide, two of whom sat silently through our interview.

Along with his wife, M.K., and their foundation, JB was the third-largest contributor to Hillary Clinton’s 2016 campaign, with $12,600,000 in donations. Jennifer, meanwhile, has ponied up “in excess of seven figures” over her lifetime, she says, to Republican candidates.

“I think they’ve just accepted the fact that I vote for who I vote for, and write checks for who I do, and they vote and write checks for who they do,” she comments. After a slight pause, Jennifer adds, wryly, “My mother voted for Eisenhower.”

“She does stand out in that way,” cousin Nick told me by phone from his home in San Francisco, speaking of Jennifer’s political leanings within the family. “She is a really admirable person. I have one point of view on a person, and another of their political views. I don’t conflate the two. I am not offended by Republicanism per se. I am offended by Republicanism as expressed by this administration.”

The greater Pritzker clan has long disliked Donald Trump for reasons nonpolitical too. In 1979, they became his partner in developing the Grand Hyatt hotel in New York—Trump’s first major project. It was a rancorous and litigious relationship, from which the Pritzkers extricated themselves in 1996, when they bought out Trump’s half interest.

As Trump began his candidacy, Jennifer says, she supported him for various reasons: “I did not want to see President Hillary Clinton. I had a lot of problems with her, and her husband. I took a rather optimistic view of Trump. I thought that because he wasn’t a politician, he would be willing to take some risks that professional politicians wouldn’t. I thought he would take more favorable positions on taxes and gun control. And I thought he would be at least as LGBTQ-friendly as any Democratic candidate.” She was “disturbed” when Trump referred to McCain as a loser, but still hung in: “I recognized he had a tendency to say impulsive things, but I felt a lot of his positions were ones I could agree with.”

Cut to July 2017. “Well that tweet hit close to home,” she says. “One ‘Aw, shit’ wipes out a thousand attaboys.” “It was his impulsiveness, his lack of thought, that I resent most,” she continues. “The military had done all kinds of surveys and studies evaluating whether the policy was feasible. Then he just arbitrarily said transgenders couldn’t serve.”

“I don’t know what he was really trying to accomplish—to placate the extreme end of his party, or create a bargaining chip for the wall? Well I don’t want to see my life, and the life of people like me, become a political poker chip. I felt he disrespected a whole category of people in a really thoughtless way, and if he disrespects one category, everybody is subject to that. Everybody has the right to be considered on their own merits.” Though she still considers herself a Republican, she says the party will have to work for any future largesse from her. “If I do donate it will be on a more selective basis,” she says. “I’m going to want to see more of a solid track record.”

In recent years Pritzker, who also serves on the board of the Chicago Symphony Orchestra, has tapped into her vast coffers to support trans rights. Her gifts include $6.5 million to the Program in Human Sexuality at the University of Minnesota; $5.99 million to Palm Center, an LGBTQ think tank, for a study on trans people in the military; $2 million for the world’s first chair of trans studies, at the University of Victoria, British Columbia; $1 million to Lurie Children’s Hospital of Chicago for a Gender and Sex Development Program; and $50,000 for the first trans-study course at the University of Toronto.