Danny's office. Jack's getting progressively drunker as he watches Simon's outburst again on TV. He starts boozily educating Simon about how, in 1983, the United States issued a formal apology to native Hawaiians for overthrowing their royal government 100 years prior, and now Jack has a house in Kauai, so you see? Insincere apologies work! "Enough," says Simon. He'll apologize. To the people of Hawaii. Before we get the chance to see if single-malt scotch reacts negatively to the human eyeball, Matt knocks on the door and beckons Jack into the hallway. "You're going to apologize," Jack assures Simon as he walks out, proving he also subscribes to Matt and Harriet's "repetition makes it so" philosophy.
Upstairs, Captain Boyle is outside Matt's office, muttering a nonspecific "I see" into the phone, as Mary scoots around him, grabs her purse, and skitters off, all the while Boyle's giving her the hairiest eyeball that ever was. We'll get to why this was stupid in a second. Back inside, Boyle does some more of that "take your mind off your troubles by making you hate me" stuff with Tom. He asks who the blonde chick is, and Tom explains how she's a lawyer defending the network against a sexual harassment claim. Boyle thinks it's fishy she's still there past 3:00 AM. Tom has no idea, but Boyle says he suspects Tom will find out soon. On cue, Matt opens the door and asks to speak to Tom for a second. Out in the hallway with Mary and Jack, Matt boils down the Trask situation as simply as he can for Tom: "Mary thinks her firm can buy your brother back." Before Tom can make us all cry again, we cut to commercial.
When we return, Matt starts to explain, but Mary realizes they're out in an open hallway where anyone can hear them, so they all duck into the control room. Matt explains the finer points of Trask: international firm, specializes in Kidnap & Ransom insurance, has contacts in Kabul. Tom, because he's a Sorkin character, conveniently knows all about K&R insurance. Mary says Trask has gotten a bead on where the hostages are being held, and Tom asks if they're sharing this information with anyone like, oh, say the U.S. military. Mary says the guy who talked to the guy who talked to the guy she talked to says they always share their info with the military. Jack picks up on the six degrees of separation between Mary and Trask's Kabul branch and asks just how far removed she is from the people who can actually do something. "I'm a sexual harassment lawyer," she deadpans. "I'm not with the A-Team." Oh, Mary Tate. Maybe we'll rescue you from Burning Studio 60 Island, too. She explains once again the people who make up Trask and how they go about doing their business. Tom asks if it's legal, and Mary says it's complicated. Her actual response is, "Let's just say 'yes.'" Love it. Cut to an angle where we can see that Captain Boyle has a full view of this Mom-and-Pop rescue mission meeting from Matt's office. Smooth. If it's legal, asks Tom, why doesn't everybody use them? Mary essentially says not everyone can afford them. Tom asks about the success rate, and Mary says it's 50/50 odds, but she doesn't get to the part about how that may or may not be better numbers than the military has. Tom's reluctant to do anything that could screw up whatever the military has planned, but just out of curiosity, he asks how much money we're talking. Jack and Matt assure him that's not a question he needs to worry about.