A Proud Boy and a progressive continue their conversation—this time, with a surprising twist. On the surface, Jack, a progressive, and Matt, a Proud Boy, couldn’t seem more different. Jack sees Trump as the biggest threat to democracy, while Matt sees the “liberal establishment” as silencing free speech and inching toward authoritarian control. Both are worried about losing their country—and both are angry. But when they role-played each other’s perspective, something shifted. Jack realized that Matt’s fire comes from the same place his own does—love of freedom, fear of being silenced, worry about what kind of world his kids will inherit. And Matt realized that Jack’s warnings about authoritarianism don’t come from “hating America,” but from the same deep fear of concentrated power crushing dissent. Neither one walked away converted. They still disagree, and sometimes bitterly. But by role-playing each other, they recognized the echo of their own fears in the other. They saw how ea...