Framhagen is in his office, pouring some clear liquor into his orange juice. Leo walks in, and Framhagen thanks him for coming over. Then Framhagen holds up the bottle and asks if Leo wants to join him. Leo declines, and Framhagen claims to have just been fooling. But I don't believe him, especially when he admits that he wishes more people in the government did drink. Leo asks him how he discovered the trip, and Framhagen lists a number of ways he could have found out. Framhagen keeps talking about the wonders of alcohol while Leo ignores him and talks about the fact that the pro-embargo stance is no longer the sure political winner it once was. Framhagen finally gets to the point, telling Leo, "It's too late for the Bartlet administration to go legacy shopping in Cuba." Didn't they already spend all their legacy shopping money in the Middle East? How much more legacy do they need? And then they have a debate. Point: Castro is bad. Counterpoint: Embargoes don't work to erode dictatorships, but engagement does. Leo tells Framhagen about the minor changes that they're actually proposing. (Minor, because the actual embargo is codified in U.S. law and can't be modified solely by the President.) After a nearly interminable debate, Framhagen stands up and tells Leo that whatever the Bartlet administration does will just be undone in a year, because any action to weaken the embargo will cause the Democrats to lose Florida in the presidential election, and therefore to lose the election. Leo mentions 1995, and Framhagen asks him what he's talking about. It turns out that Framhagen was somehow involved in swinging the results of the recount in the Congressional election that year. Framhagen mentions the fact that he and Leo got plastered together. Framhagen tells Leo, "We were close once, back then." Leo responds, "No, Senator, we just drank back then. We were never close." And with that burn, Leo leaves the room.
Kate sits alone in the empty Sit Room. Leo comes in and tells Kate that he's been looking for her. She tells him that Jed is going on the air any minute, and she wanted to watch from the Sit Room. He sits down, and starts to ask her about what she was doing in Miami in the '90s. She confirms that she was there, but doesn't say much else. He says that he was there for a few days in '95, but that he doesn't remember much about it: "Led me to lock myself away for thirty days, dry out." Which is true except for the fact that it happened two years earlier. He tells her that he thinks the fight over Cuba is worth it, and she responds, "There's gonna be hell to pay tomorrow." If we see the tiniest sign of fallout from this episode before the end of the season, I will eat my hat. Leo thinks that if he could have gotten something done ten years earlier, Jed would be spared the need to fight the same battle now. Kate cuts him off, saying, "The CIA would have never let the embargo go away then. They're against ending it now." So, what? They would have assassinated Leo back in '95? He asks her what she thinks, and she tells him that she supported the embargo in '95, but that she's not sure what she thinks anymore. Leo gets up to leave, but before he goes he asks her, "Did we meet back then?" She asks him if he remembers her, and he doesn't. And then he asks her if she remembers him. Strum strum strum. And...flashback!