It's the old "meet society where it is" vs "push society forward by supporting the thing" debate. His proposed granular approach didn't work for gay rights, and it hasn't for trans rights. It took things like ACT UP's more blunt approach to shift public opinion on gay equality.

The US tends to be conservative, so real change only comes when large numbers of people are forced to rethink their views. The Democratic party taking credit for big changes but never really pushing for them, or actively standing in the way, is one of the main criticisms of the party.