"There were certainly plenty of points where people told me it wouldn't work, but I always believed we could do this. I always believed this was the right strategy," Wolfson said in an interview conducted before the Supreme Court's ruling Friday.
The ball got rolling slowly. In the '90s, a challenge to Hawaii's ban on same-sex marriage seemed to be making progress—but then voters in the state approved a constitutional amendment that abruptly cut short the push for marriage equality there. (The same success and setback would be repeated a decade later in California, where Proposition 8 effectively reversed a state Supreme Court decision allowing same-sex marriage.)
The first real legal breakthrough came in 2003, when the Massachusetts Supreme Court ruled that a ban on same-sex marriage violated the state constitution. "Civil marriage is an esteemed institution, and the decision whether and whom to marry is among life's momentous acts of self-definition," Judge Margaret Marshall wrote in one widely quoted section of the ruling.
For every step forward, though, there were setbacks. The 2000s saw roller coasters of activity, often reversing course even within one state.
Wolfson recalls one "particularly horrible" month in 2006, when Freedom to Marry and its allies lost four consecutive cases—in New York, New Jersey, Maryland, and Washington. They would later win marriage equality in each of those states through legislation, but the litigation losses took a toll.
"We were being strategic, but none of it is easy," Wolfson said.
Proposition 8 passed in 2008; but then 2009 turned out to be the movement's most successful year yet, with victories in four states. One of them was Maine, where the victory was erased at the ballot box in 2009, Wolfson said, then restored via another ballot initiative in 2012.
Thanks largely to legislative wins, including a major victory in New York, Wolfson felt that momentum already was on his side in 2013, when the Supreme Court agreed to hear challenges to California's Proposition 8 and the Defense of Marriage Act, the law that prohibited same-sex couples from receiving federal marriage benefits.
The court punted on Proposition 8, effectively allowing same-sex marriage to proceed in California without answering the broader question of whether the Constitution forbade states from banning it. But Kennedy's decision striking down the critical part of DOMA was nevertheless a clear signal that the court was on the side of marriage equality, and even Kennedy's critics said a nationwide ruling appeared to only be a matter of time.
"One of my main concerns was people pronouncing it inevitable too early," Wolfson recalled. "I used to say, 'Ten minutes ago they were telling us it's impossible; now theyre telling us it's inevitable' "¦ Both are ways of excusing yourself from doing the work."