For two decades, Paul Ryan worked both publicly and behind the scenes for immigration reform. Now, he’s preparing to leave office as the House Speaker who refused to move any immigration bill to a vote until his party forced him to.

Paul Ryan’s legacy on immigration may end up being nothing at all — barring a twist in the next few months, he will join a long line of Speakers who weren’t able to pass comprehensive immigration reform under their watch. But in Ryan’s case, he spent much of his Speakership blocking the types of bills he used to promote, and boosting the ones he used to fight against.

As a staffer in the 1990s, Ryan helped kill a bill that slashed legal immigration. As Speaker, Ryan spent months pushing a bill that would do just that. As a Congressman in the 2000s, Ryan signed endorsed bipartisan immigration reform plans. As Speaker, he employed his might to block a bipartisan bill from reaching the floor.

Such conversions typically don’t happen overnight. But Rep. Luis Gutierrez, a Democrat who used to work with Ryan on the issue, believes that Ryan’s breaking point did happen in a day. One specific day, in fact — June 10, 2014.