Jake is reprimanded by Deputy Commissioner Podolski when Lucas Wint files a formal complaint against him. Wint claims that Jake has been harassing him, however, Jake tries to assure the deputy commissioner that he has only been trying to ask Wint some questions.
Through chatter from lowlifes, Jake has heard rumors that Wint is laundering money for drug dealers. Due to Wints high profile, Holt orders Jake to drop the investigation.
Later, Jake fools Amy into thinking they are staking out a burglary case. In fact, Jake is still tailing Wint. He tells Amy that he saw Wint with a drug dealer the previous day and is looking to get photographic evidence this time. While they are hiding in an unmarked police vehicle, Wint discovers them, and Jake is once again reprimanded by Holt.
Against her usual nature, Amy stands up to Holt and admits that she believes Jake is on to something with this investigation. Holt tells her to mind her own business and informs Jake that he is being put on administrative leave. Jake will later have to appear in a hearing where he is facing a six month suspension.
On a later date, Jake asks Holt to meet him in an alley in Bensonhurst at 9:00 in the morning. There, Jake reveals that Amy, against Holt's wishes, discovered an informant with incriminating information on Lucas Wint.
The informant is Isaac, a drug pusher for the Bay Ridge Boys. He informs Holt that every Friday he puts cash into a duffel bag and brings it to the Wint Community Center. There, he marks the transaction down as a charitable donation in their account books. This proves that Lucas Wint is laundering money. With this information, Holt agrees to assist the detectives with their case.
Together they go to the courthouse to request a warrant from Judge Mindel. Once they are granted the warrant, the detectives devise a plan to sneak into Wint's community center undetected. At that time, there is an amateur ballroom dancing competition taking place. The detectives head to a thrift store to retrieve costumes and then enter themselves into the competition.
In the community center, Jake is able to sneak into the accounts office and take photos of the incriminating evidence in the books. Before he can state his case against Wint, Holt informs Jake is informed of a larger investigation being conducted by the FBI.
Lucas Wint is suspected of being involved with the Ianucci crime family. Jake gets himself purposely fired from the NYPD in order to take part in an undercover investigation to find moles within the NYPD that are helping the Ianucci's.