Not many of us are pioneers, but Tom Stoddard was. He fought for equality for lesbian and gay Americans before it was respectable; he was proudly out as a gay man before it was professionally safe to be out; and he taught one of the first courses centering on the rights of lesbians and gay men in any American law school. He lived to see the lesbian and gay civil rights struggle take its place with others as a campaign for human dignity and justice. Tom’s final Essay, Bleeding Heart Reflections on Using the Law to Make Social Change, is a reflection on the relationship between litigation, legislation, and the possibilities for law to operate as “culture-shifting” rather than merely “rule-shifting.” I argue that the litigation-legislative dynamic is more structurally complicated than the description in Bleeding Heart suggests, and highly contingent on the historical moment. I comment on what I think is one of the most significant aspects of the Bleeding Heart argument: the implicit assumption that lesbian and gay rights advocates have the potential to regularly win in the legislative arena. Lastly, I offer some thoughts on how one can more consciously seek a culture-shifting practice of law.