Sara is looking at her sunburned back in her bedroom mirror. Drew enters in good spirits and offers to rub lotion on her back for the pain. Sara seems quiet and distant and Drew asks her what's wrong. Suddenly, there's a flash to Thatcher trying to strategize with Jack and another man about how to get Drew off his family's back. The guy says Drew is pretty clean, but there is something they could use on his wife: she's sleeping with someone else. He looks right at Jack. There's another flashback to Sara and Drew in their bedroom. Drew whispers into Sara's ear that he knows she's been seeing someone.
One day earlier
Jack goes to see Sara at her studio, but they are quickly interrupted by Sara's co-worker, Alissa. After Jack leaves, Alissa asks her if that's the guy she's been seeing and wants to know if she's considered going to see the therapist she mentioned earlier. Sara says she's thinking about it, but may not end up going. Alissa recommends at least giving it a try as a way to help Sara figure things out. She says it's cheaper than a divorce lawyer.
It turns out that Thatcher is involved in a romantic on-again, off-again relationship with the judge presiding over TJ's court case. As Monica gets around for work, Thatcher explains to her that he needs her help with TJ's case—something she's apparently done multiple times in the past for various things. But this time is different. She tells Thatcher that times are changing and she just can't help him out on this one, though she'll call him the next time she feels like hooking up.
In light of Connie's disappearance, TJ is up for another bail hearing. Judge Monica decides to set bail at one million dollars, though it's hard to tell if she did it for Thatcher or because Jack made a side deal with her as well. Either way, TJ gets temporarily released.
Back at the office, Jack asks his go-to IT, Jules, to destroy some files for him. She happily agrees, but informs him that she asked his daughter Val out on a date. He's well aware that she's gay, but he thinks Jules may be a little too old for her. Eventually he does agree to them going on one date together, to which Jules is extremely grateful.
Things aren't going well for Thatcher, however. In light of this whole scandal on his family, banks aren't backing him like they usually do and the people working for banks aren't paying him the respect he thinks he deserves. Thatcher tells Jack that he seems distracted and he needs to get his head in the game if they plan on making it out of this mess in one piece.
Jack has other things on his mind these days—like finding a way to hang out with Sara without getting interrupted. He asks her to spend the night with him on his boat since they're both supposed to be away on business anyway, even though hers got recently cancelled. She agrees and goes to meet him shortly thereafter. Unknown to them, they get photographed kissing at the docks.
Drew gets his hands on a bug, so he can listen in on all of Thatcher's secret meetings in his office. Now he just needs a person to plant the bug, which is where TJ's semi-girlfriend Brandy comes in. After threatening to deport her from the country if she didn't cooperate, Brandy placed the bug behind a picture frame of Jack and Elaine right in Thatcher's office during TJ's "congratulations for getting out on bail" party later that evening.
TJ goes to see a guy named Roger who works at a car repair shop. He says that the guy's brother, Omar, was nice to him while he was in jail and wanted him to pass along a message to Roger when he got out, which was simply "91J." Roger thanks him for the message and TJ introduces himself as a Karsten. He lets TJ hang out at the shop, telling his friend that he enjoys having the guy around. He doesn't plan on being a part of any criminal activity his brother is trying to get him involved in regarding the whole "91J" message. But when he's cleaning out the trunk of TJ's car for repairs, he stumbles across a gun stashed away, though it's unclear what he plans on doing with it.
Thatcher meets Drew outside his son's elementary school and basically informs Drew that he appreciates his tenacity, but he needs to stop coming after him if he knows what's good for him. "There are a lot of ways to get lost in Chicago." Make sure you've got a map," Thatcher warns.
After a night on the boat, Jack and Sara are about to go their separate ways when Jack notices someone photographing them a little ways away. Without telling Sara, he goes to investigate and discovers that it's Derek, a guy who works for Thatcher. He was assigned to do some digging on Drew and it led him to Sara's little affair. Derek makes Jack a deal: he won't tell Thatcher about Jack's role in all this if he gets to be a full-fledged member of Thatcher's inner circle.
Later that night, Derek, Jack, and Thatcher meet up with Bernard, a member of the zoning board who's now refusing to back Thatcher in light of the whole TJ scandal. This makes Thatcher revert to ways of torture via a nail gun to the guy's hands. Afterwards, conversation turns to Drew and what Derek's been able to dig up on him, bringing the episode back to where we started at the beginning.
Thatcher is happy to learn that Drew's wife is having an affair and wants to find out who the guy is, so they can work with him to help bring Drew down. Due to their agreement, Derek hasn't blown the whistle on Jack yet, but it feels like it's only a matter of time before the truth comes out. Thatcher heads into his office with Jack, where the FBI are now listening thanks to the planted bug, where he officially declares war on Drew. Jack looks nervous.
Meanwhile, Drew is back to informing Sara that he knows she's been seeing someone. Sara immediately looks terrified, but it's not what she thinks. The therapist Alissa had set her up with had called Drew's office to confirm their upcoming appointment. Drew informs her that he thinks it's a good idea for her to see someone if she's feeling stressed. Sara looks both relieved and guilty.