Throughout the Series
In Chocolate Milk, the precinct is being assessed and Holt is happy as his old captain is conducting the assessment. However, this joy is tarnished when his arch-nemesis, Wuntch, arrives instead. Amy freaks out at the thought that Wuntch will fail them. After a disastrous assessment, Amy tells Holt that, in order to boost their score and prevent himself from being fired, he has to grovel to Wuntch. Holt states that he won't and reveals to Amy that he and Wuntch once got along very well in the past. However, at a time when he was up for big promotion, Wuntch tried to seduce him and was embarrassed when he revealed he was gay. For this, he believes that she sabotaged his chances of gaining the promotion. Amy would later discover that Wuntch's recommendation letter was actually positive. This confuses Holt, who had assumed that she sabotaged it because he was gay, but Wuntch explains that his sexuality is the only thing that she respects about him. However, she reveals that she remains furious about numerous other things and angrily leaves. Holt, following Amy's advice, grovels to Wuntch and she passes them (but only just).
In The Jimmy Jab Games, Holt and Terry approach Wuntch to get her approval for the money needed to tackle the drug "Giggle Pig". Wuntch rejects them as they used incorrect punctuation, so Holt goes behind her back to see the Chief. Wuntch argues against Holt and Terry, but they eventually succeed in obtaining their task force for the drug bust. However, Wuntch informs them that she did it on purpose: she had forced them to oversell "Giggle Pig", and now they had better get the task force to work.
In The Mole, Wuntch hears that internal affairs have been sent to find a mole. She mocks Raymond for it and also disparages his task force. However, Jake discovers that there is no mole. The inspector from Internal affairs is actually working as a spy for Wuntch to get access to the task force. Wuntch agrees to back off after Jake and Holt secretly record her.
In Stakeout, Holt, Rosa and Jake are getting commendations from Wuntch for their help stopping "Giggle Pig". Holt doesn't know whether to take the high horse or tell her his "burn", which is "Wuntch time is over". Holt takes the high horse, and Wuntch is surprised that he doesn't gloat at all. He solemnly thanks her and then walks away. As she does, Holt shouts his burn and laughs as he had it both ways.
In Defense Rests, Wuntch needs Holt's help for a promotion, but she is worried that he won't give her a good recommendation. Rosa advises Holt to give her the recommendation, and he does. However, she reveals that she negotiated another promotion, so she won't have to move. She then kisses Holt suddenly, saying that she knows he wouldn't have recommended her if he didn't think she deserved it. She leaves, leaving Holt confused.
In The Chopper, Wuntch comes into the precinct, and Holt expects her to take the case. Instead, she says she will give them anything they need to succeed. They eventually solve the case but Wuntch reveals that she wanted Holt to succeed so that she would have an excuse to promote him to a boring desk job.
In Johnny and Dora, Holt gets Gina and Terry to find a rude letter that Wuntch wrote about the Chief in hopes of overturning his promotion. When Holt meets with Wuntch, she pats him down to check he's not wearing a wire. He reveals he has the letter and tells her that she has to overturn his promotion. However, she later tells him that she will deny that she wrote it and in that time she can make some changes to the staff, effectively splitting up the 99th precinct if he doesn't leave. Holt is forced to comply and leave.
In New Captain, Wuntch refuses to let Holt make improvements to the PR department such as his eight-point plan on community engagement. Instead, she angrily forces him to name the community mascot, a pigeon, after they fight in front of the other employees. Holt tries to get her to put her pettiness aside and improve the department, and she agrees to let him "spread his wings". However, she instead makes him wear the pigeon mascot costume.
In The Oolong Slayer, after Holt's disaster with his posters, Wuntch humiliates him by assigning his employee, Bob, to keep an eye on him. Later, Wuntch is disappointed in Holt when he is discovered to be working on a case secretly.
In The Suicide Squad, Wuntch initially seems to accept her role in Jake's scheme to expose Commissioner John Kelly's illegal crime-solving tactics. However, she ends up sabotaging Jake's first plan involving C.J's fake kidnapping, stating that Holt would never trust her with the operation anyway. Jake manages to convince her to return and be involved in a new scheme. Holt is forced to pose as her 'lover' so that no one would question his presence beside her. However, Wuntch ends up betraying Holt and teaming up with Kelly. In the time she was out of the squad, she made a deal with The Vulture to make him Captain of the 69th Precinct (his dream job). With their hands 'clean' and C.J on their side, Kelly initially has the upper hand in the situation. However, when he opts to celebrate his victory with photos, Wuntch double-crosses him, revealing that Jake's actual plan was to make it appear that she had become a turncoat in order to access Kelly's phone. Securing the information they needed, the squad forces Kelly to step down as the Commissioner, which allows Wuntch to step in as Acting Commissioner. Disgruntled at Holt's claims that he became a detective within a month (something that was not allowed), Wuntch demotes Holt to traffic control. This allows the 99's budget to open up, preventing Terry's transfer to Staten Island.
In Ding Dong, Wuntch dies unexpectedly. After her death, Holt gets sent a video that Wuntch recorded before she died. In the video, Wuntch explains that she told everyone that Holt was planning her memorial service. Knowing that Holt would be unable to stop himself from badmouthing her at the service, this was Wuntch's final ploy to end Holt's career. It's revealed near the end of the episode that she also promised half her estate to her nephew, Adam, under the condition that he records Holt badmouthing her before the service as assurance for her plan.
Wuntch was intelligent and cunning. She could nurse a grudge and had a long-term fight with Holt until her death. However, she was not as vicious as to smear Holt because he rejected her romantic advances, as he wrongly assumed. In fact, her recommendation letter for him was actually positive. In addition, she knew when to admit defeat as she allowed Holt to gloat and also backs off of their feud if her career was at stake such as in The Mole.
Holt and Wuntch were enemies. They were constantly shown to be antagonistic toward one another, and Wuntch was one of the few people who truly angered Holt. However, strangely Wuntch retained unrequited feelings for Holt from their early days working together.
- Madeline blamed Holt for embarrassing her in front of Derek Jeter, although Holt claims she embarrassed herself.
- Holt admits to tripping Madeline into Michelle Obama, which she still remembered until her death.
- It is never revealed how Madeline died, however, it's strongly implied that she knew she was going to die well in advance.