At a bar, Chance is wearing handcuffs and his "friend," Harry the private detective, spots him and comes over, explaining he was there for a blind date. Harry insists on staying even when Chance tells him to go away, and Chance then tells him to cheer the race on TV or they both die. A man in a suit comes over and looks over Harry, who notices he has a gun. Harry hastily starts cheering and the man goes away, satisfied. Once he's gone, Harry asks who that was, but Chance tells him to shut up and listen.
48 hours earlier
Winston brings in a new client, Sarah Han, who explains that her fiancé Harry Claypool has threatened to kill her. Claypool runs a global VIP protection racket and is a famed recluse who lives at a secluded manor in Marin. Sarah caught a glimpse of his computer files and learned that he runs a private hit squad for hire. Claypool realized what she learned and threatened to kill her if she told anyone or left him. Ilsa comes in and calls Guerrero out into the hall, and asks what kind of progress he's made on tracking the woman in the photo with her husband. Guerrero tells her that the woman has hid her identity, and says that in his opinion she was Marshall's mistress. Ilsa refuses to believe that, but Guerrero insists that he's sure.
The team tries to find a way into the compound to get the files and tie Claypool to the hit squads. The computer is isolated so they'll have to break in. Winston explains that the outdoor security is airtight, with a company of elite private security. Claypool's office has a temperature sensor and laser grids on the floor. Sarah blames herself, but Winston assures her that they're there to help her, not assess blame. Ilsa has been watching the entire thing from the doorway, and she introduces herself to Sarah. Chance talks to Ilsa outside, and she says that she wants to help get Claypool to help Sarah and because Claypool tries to work with the foundation. Chance figures that she's taking out her frustrations over the discovery of Marshall's mistress, but Ilsa insists that she's just trying to help Sarah.
Harry is surprised that Chance allowed Ilsa to go on the mission, but Chance insists that she had a good plan. However, the job went south and one of the team didn't make it out. Chance explains that in ten minutes, they'll exchange the stolen information for the prisoner... and he's the prisoner. He shows Harry the handcuffs, and the fact that he's wired to a bomb attached to the bottom of the chair. Chance suggests that he can leave, but Harry refuses to abandon him. With eight minutes left, Chance tells him to order a martini with extra olives. Harry agrees, but wants Chance to tell him everything that happened.
Winston tells Ames that she'll team up with Chance, and she wanted to spend some quality time with her. Meanwhile, Guerrero inserts sodium thiopental into a $9,000 bottle of wine to render Claypool incapable of lying. As Ilsa prepares to leave, Winston and Guerrero complain that it's risky to give Ilsa a major role in the operation. Chance insists that he has it under control, but they're not convinced.
Guerrero is the limousine driver who brings Ilsa into the compound to meet with Claypool. Chance and Ames are concealed in a hidden compartment. As they go in, Guerrero tells Ilsa that Claypool eliminated the last man who tried to sneak into the compound, and he's buried somewhere in the ground. Ilsa refuses to be scared off. In the trunk, Ames asks Chance if he's seeing anyone romantically. She offers to set him up with a friend, Melanie. Chance tells her to focus but Ames persists.
When Guerrero pulls up, security chief Vaughn and his men search the trunk but fail to find the hidden compartment. They send Guerrero to the kitchen, park the limo, and escort Ilsa to see Claypool. The manager tells Guerrero to stay in the kitchen and fold napkins. He complains to Winston over the earbud, and Winston tells him to wire into the system. Guerrero activates the system and Winston gains access to the cameras.
Chance and Ames emerge from the limo and sneak inside while Winston directs them past the security guards. Meanwhile, Ilsa meets Claypool on the outside balcony and gives him the wine as a gift. They notice Sarah riding and Ilsa admires the horse. Claypool doesn't see the appeal.
Ames and Chance get to Claypool's office and Ames crawls across the shelves to the temperature sensors. She uses a small fan to cool the sensor, while Chance spots the lasers with an aerosol spray. He then crosses over the tables and staircases, only to discover that someone has moved the table he needs to get to the computer desk. Winston tells him to stay put until Ilsa gets the password.
Claypool summons Sarah to his study and pours Ilsa's wine. She offers to hire his services to protect the foundation's aid camps. Claypool considers it and then invites her to drink the wine with him. Ilsa claims that her doctor advised against it, and Claypool puts his wine down. Winston tells her to be calm, while Guerrero figures that she blew it and starts to head out. Winston and Chance tell him to stay put rather than blow his cover. Ilsa finally comes up with a plan: she offers a toast and drinks the wine. Once he's satisfied, Claypool drinks his glass of wine. The team realizes that she just dosed herself with the sodium thiopental.
Harry returns from the restroom and hands Chance one of his sock and the toothpick from the martini. Chance tells him to buy a specific bottle of Scotch from the bar shelf, and Harry obliges. Harry then notes that Chance never let him come on a mission, and wonders why he let Ilsa go on the mission. Chance insists that it was her plan, but Harry says that she wasn't thinking straight. He tells Chance to continue with the story.
Both Ilsa and Claypool feel ill. Ilsa immediately tells the truth and admits that she gave him a dose of sodium thiopental to get the password. Chance tells Guerrero to wait, while Ilsa and Sarah team up to tie Claypool to his chair. Winston tells Chance to get to the computer, and Guerrero to help Ilsa. Guerrero uses a steamer to block the security camera. Meanwhile, Chance tries to jump to the distance table. Distracted, he loses his balance and falls. He ends up suspended between the table and the computer desk, hanging on for dear life.
Guerrero gets to the study, punching out the manager in the process. He goes to the study and interrogates Claypool, getting the password and transmitting it to chance. Chance enters it and starts downloading the file, which will take three minutes.
Vaughn finds the streamer in the kitchen and realizes that something is wrong.
Guerrero starts to take Ilsa and Susan out, but Vaughn knocks on the door. Sarah warns that once they realize Claypool is tied up, they'll look up the compound. Ilsa opens the door and blocks Vaughn, and stalls by complaining about his face. Meanwhile, Guerrero gets Sarah to the car and briefs the others, admitting that Ilsa has stones. The files finish downloading and Ames wonders what they're going to do.
Claypool manages to knock over some books, alerting Vaughn. He has his men grab Ilsa when she tries to run. Chance hears the entire thing on the earbud, throws the flash drive to Ames, and tells Winston that he's going to rescue Ilsa. He insists that he's got it under control and then drops to the floor, setting off the alarms.
The troopers start searching the grounds, and Vaughn warns Ilsa that her friends won't escape. Ames gest to the limo just as Guerrero pulls out. He drives for the gate, evading enemy fire, and Winston blows the gate so they can make good their escape.
Chance heads for the study and Vaughn realizes that he's coming when his men warn him over the radio. They open fire when a man comes in the door, but it's one of their troopers. Chance slides beneath him and down underneath the table, takes out Vaughn's men, and rescues the dazed Ilsa. They head out onto the grounds and Ilsa tries to apologize. She admits that she is upset because she found out about Marshall's mistress. Chance interrupts to say that he smells crap: horse manure from the nearby barn. He and Ilsa ride out and a trooper on a motorcycle chases after them. They lose that trooper, but Chance warns that they can't overrun all of them. He temporarily loses the other pursuing guards and gets off, telling Ilsa that they can bargain for his release later. Chance explains that he knew something might happen if he let her come along, but refuses to say why he did bring her along. As she rides off, Chance fires two shoots to attract the troopers.
At the bar, Chance explains that Ilsa will arrive with the information and trade it for Chance. Harry tells Chance that he's off his game because his judgment is clouded due to Ilsa's involvement, and he has feelings for his boss. Ilsa arrives and meets with Vaughn, who takes the flash drive and verifies that the information hasn't been copied. Chance tells Harry to buy him some time, while Claypool arrives and tells Ilsa to sit at the bar with Chance. Harry offers to tie a cherry stem with his tongue to distract Vaughn and Claypool, and Vaughn punches him. One of Vaughn's thugs punches him unconscious. Meanwhile, Chance opens the handcuffs using the toothpick as a lockpick, wedges the bottle between the bar and the chair to hold it down, and gets clear before breaking the bottle with a thrown shot glass.
In the chaos, Chance knocks out one of Vaughn's men, takes his gun, and gets Ilsa to cover. They exchange fire and Chance complains that Ilsa didn't anticipate a double-cross. Chance runs out of ammo and Vaughn moves in for the kill... and Guerrero kills him with his belt blades. Winston captures Claypool as he tries to escape. Harry claims that he handled himself amazingly well.
Ilsa gets out and Winston uses his connections with the police to cover up her presence. Chance insists that he and Harry could have handled it, but Guerrero and Winston explain that they set up the blind date with Harry to get him there. They figured that Vaughn's men would never suspect him, but Harry would still manage to mess things up for the bad guy. Before they go, Ames tells Chance that she knows why he doesn't go on dates: he has a crush on her. The rest of the team leaves in disgust, and Ames fails to notice Harry trying to pick her up.
Back at the agency, Ilsa is in her office drinking and looking at the photo of her husband with the mystery woman. Chance comes in and tells her that they covered up her involvement with the authorities. Ilsa admits that she shouldn't be tearing herself up about Marshall's affair, but can't control what the knowledge is doing to her. She wants to remember Marshall like he was with her. Chance tells her that if Marshall cheated on her, he was an idiot, and she deserves a lot better. Ilsa looks up at him for a minute and then kisses him.