This post contains spoilers from Only Murders in the Building season 5 episode 2 from this point forward.
Even though Only Murders in the Building season 5 opened with some real shockers — Lester's connection to Nicky Caccimelio, the underground casino at the Arconia, and Nicky's dead body falling on Oliver — the second episode takes an immediate step back from the story at large to given some insight into Lester's life and work as a doorman. The second episode begins with what's seemingly a documentary film about doormen working in New York City.
Before his death, Lester had been the Arconia doorman for 32 years, but he didn't plan on making this job his career. He wanted to be a movie star. The episode flashes back to Lester's first day on the job, with Emory Cohen playing the younger version of Lester. The building's then-doorman George (Tony Plana) mentored him from day one on all the tenants, the inner workings of the building, the iconic elevator crank, and saying "After you."
Interspersed throughout the flashback episode are brief black-and-white clips of the night Lester died (and episode 3!). We even get to see Mabel as a baby the first time she met Lester and all of the first encounters Lester had with Oliver, Charles, Howard, and more residents. George instructs him to remove a "homeless woman causing a racket" in the courtyard, but that's how he met Lorraine, who was singing to her babies in their stroller. Before long, the pair are married.
How Lester became involved with Nicky Caccimelio
The flashback flashes forward to Christmas in 1999. Mabel gets in trouble from George for hiding in the closet in the lobby (yes, the one where they found the hidden door to the underground casino in episode 1), but Lester befriends her and allows her to shadow him while he works. George gifts Lester with the official ledger with all of the building's secrets. George was working closely with Nicky Caccimelio, who gives him envelopes of cash. Lester wants in.
Once the automatic elevator is added to the Arconia and the crank isn't necessary, Lester fears he will lose his job. George introduces Lester to Nicky Caccimelio. They relate to each other over Lester being from Flatbush. George plans to retire and he's grooming Lester to take over for him to work with Nicky. He would work late on Saturday nights to let people in the building for Nicky. He agrees to the terms without knowing exactly what everything entails.
As the years go by, Lester falls right into order with his new position as the main doorman at the Arconia. The flashback catches up to just before present day as Mabel heads up to her place with her friends Tim and Althea (Beanie Feldstein). After hours, Lester meets with Nicky at the dry cleaner asking for Saturday night off for his anniversary. Nicky says no, and he doesn't react kindly to Lester suggesting that he will retire. He's beholden to Nicky.
Even though he was stuck with Nicky, Lester still gave his job his all, offering words of wisdom to Oliver and some spare cash to Charles when they needed it most. Lester questions his job as murders continue to happen in the building under his watch. He hired Randall as an extra doorman for some help. Just as George did, he mentors Randall, but he doesn't allow Randall to get involved with Nicky. On the night he died, Lester's shown dropping his crank and hitting his head on the fountain. Someone wearing gloves picks up the crank off the ground.