|“||Once you're in, you're never out.||”|
Simmons is introduced as an old friend of Detective Fusco and a high-level enforcer for HR. He works as a street cop. Fusco first contacts him, on instruction by Reese, as a way to infiltrate HR. After Reese kills corrupt IAB Detective Ian Davidson to save Fusco's life, he tells Fusco to call Simmons to help him cover up Davidson's death. Simmons agrees to help Fusco, but warns Fusco that he (Fusco) now belongs to HR. (“Blue Code”)
Simmons and HR are in collusion with up-and-coming mob boss Carl Elias. When Elias kidnaps his father, mob boss Gianni Moretti, Simmons tasks Fusco with finding out where Detectives Joss Carter and Bill Szymanski have hidden Moretti. Although Fusco discovers Moretti's location he doesn't divulge it to Simmons. (“Baby Blue”)
Simmons and HR ally themselves with Elias in his war to take out the Mafia dons. Simmons asks Fusco for anything he can find on "the Man in the Suit" and warns him to take the next few days off as Homicide will be backed up. While surveilling Elias' men, Reese finds one watching Simmons with his family and realizes that Elias is positioning himself to have leverage over HR. Finch later brings this proof to Simmons and convinces him to sever HR's ties with Elias and locate Taylor Carter for rescue. As a result of the meeting, Elias' HR reinforcements abandon him, enabling Carter to arrest Elias with the help of Fusco and some clean cops. (“Flesh and Blood”)
When HR receives a contract to kill Caroline Turing, Simmons enlists Fusco's aid after introducing him to city councilman and leading HR member Seth Larsson. Simmons and his men corner Reese, who is protecting Turing, in a parking lot and a shootout ensues. Fusco and Carter arrive and rescue Reese as Simmons's men close in. Simmons walks away from the shootout unscathed. (“Firewall”)
As a result of a sweep by FBI Special Agent Nicholas Donnelly, over 75 members of HR are arrested by the FBI. Simmons confronts Fusco and forces him at gunpoint to help them find an HR ledger recording bribes paid to HR members. When Fusco finds the ledger, he tears off the pages containing Simmons and his own name, thus preventing them from being arrested. Simmons then meets the previously unseen head of HR, Alonzo Quinn, and they decide to rebuild HR. After the arrests of the leading HR members, Simmons is now the number two man in the organization and handles their activities on the streets, while Quinn operates in the shadows. (“Bury the Lede”)
Simmons later meets with Quinn and tells him that he made sure that arrested members of HR will keep silent about him and Quinn. When Quinn decides that they need to renew their friendship with Elias, Simmons contacts Elias' right hand man Scarface. However, Elias betrays them and has one of their men killed. Fusco also severs his ties with HR and walks away. As a result, Simmons gives an anonymous tip to Carter that another cop murdered Davidson. (“C.O.D.”)
Simmons arranges for Peter Yogorov to meet Quinn, who proposes that they forge a new partnership. Yogorov agrees, on the condition that HR guarantees that he and his brother will not be prosecuted. HR then frames Detective Bill Szymanski, painting him as a dirty cop in an effort to stop him from testifying against the Yogorovs. When Carter clears Szymanski's name, Yogorov's faith in HR is shaken, but Simmons tells him to trust his boss. Quinn murders both Detective Szymanski and the ADA Melinda Wright, effectively ending the prosecution of the Yogorovs. (“All In”)
Simmons meets with Quinn after Cal Beecher questions Quinn about Detective Szymanski's murder and the information Quinn supplies him about cops and dirty money. Simmons asks if Beecher is going to be a problem and Quinn says he hopes he won't be. When Beecher meets with Elias to verify what Quinn has told him, Simmons learns about the meeting and tells Quinn. He suggests that Quinn could give Beecher a promotion or transfer him out of the city. Instead, Quinn orders Beecher's murder. Later on duty that night, Beecher is set up by his CI and killed in a shootout by the Yogorovs. (“Trojan Horse”)
Simmons is present at Detective Beecher's funeral, where Quinn delivers a stirring eulogy. After the service, Simmons is confronted by Fusco, who claims he knows that he had something to do with Beecher's death. Simmons tells him that he doesn't have HR's protection anymore and hints of what would happen when his former friends talk to Internal Affairs. Fusco threatens Simmons with what he knows, but Simmons is not intimidated.
Later, in Oyster Bay, Simmons is present while IAB detective Joseph Soriano leads the search for Detective Stills' body. He taunts Fusco, whispering "It's only a matter of time". However, he is soon proven wrong, and is shocked when the grave is found to be empty. (“In Extremis”)
When Carter looks into HR after Beecher's death, Simmons calls Detective Terney, telling him that Quinn wants Carter eliminated. Although the original plot to kill her was foiled, HR manages to frame Carter for shooting an unarmed suspect. (“Zero Day”)
When HR finds out that a young hobby spy recorded their meetings with the Russians about the manufacture of a new drug, they abduct the girl and Simmons keeps her in in their drug lab. After unknowingly getting false intel from Mike Laskey, Simmons believes he can recover the recordings and also take down Reese in exchange for the girl. At the meeting location, Reese disables two men who were working with Simmons, and he fights Simmons in a brutal fistfight with Simmons holding his own before Reese finally takes him down. Simmons tells Reese that there are hundreds of them but Reese assures him that HR will be brought down and disappears just as the police arrive. (“Razgovor”)
Simmons later shows up to scold Laskey when he doesn't realize that his neighborhood friend is skimming from HR. He then reveals that he killed the man and stuffed his body in a trunk of a car. He orders Laskey to bury the body where no one will find it. (“Mors Praematura”)
Simmons monitors a meeting between Quinn and an unsuspecting Carter. Later, Simmons gives orders to Laskey for the killing of a sports memorabilia store owner who has been working to launder HR's dirty money. He meets with Terney and angrily instructs him to locate the store owner and a signed baseball that the man purchased at an auction with HR funds. (“The Perfect Mark”)
Simmons later meets up with Peter Yogorov at an abandoned brewery in Redhook to try to renegotiate the terms that HR wants for their services protecting the Russians' drug deliveries. Yogorov complains to Simmons that the Russians are doing HR's dirty work and considers cutting ties. Simmons warns Yogorov that HR will no longer protect his drug shipments if he refuses to agree to the terms, but Yogorov says he'll take his chances. Unbeknownst to them, Carter captures the entire incriminating conversation from across the river using a parabolic microphone.
Carter, who has now deduced Quinn's identity as the head of HR, orchestrates an elaborate plan to turn HR against the Yogorov family. She attacks a drug shipment, stealing a delivery truck and all its contents. Yogorov suspects that HR stole the shipment in retaliation for his refusal to accept their new terms. Carter then takes several sniper shots at Quinn's office while he's on the phone with Simmons. Both Quinn and Simmons suspect Yogorov, and Quinn orders Simmons to round up all the Russians.
Simmons is present along with Quinn and two other HR members when corrupt judge Andrew Monahan lures Carter to his house and betrays her to HR. Simmons and the other men hold Carter at gunpoint, but Reese stages a surprise attack and quickly disables most of the HR members. Carter apprehends Quinn after Reese fires a carefully aimed bullet into his shoulder to prevent him from escaping. Following a distress call from Simmons, another HR officer arrives in his police car, but Reese quickly fires at him, forcing him to take cover. Meanwhile, Reese disables the police car by shooting key components of the engine and then disappears with Carter and Quinn. Simmons walks out of the house and accesses the car's still-intact camera system. He sees that it has captured a picture of Reese, and orders the officer to send it to every cop and criminal in the city. Simmons vows that "the man in the suit dies tonight". (“Endgame”)
When Monahan warns Simmons that HR will be charged and asks what their cover-up story will be, Simmons concocts a cover story that "armed robbers broke into the house, looted the place and shot him". Before Monahan can react, Simmons shoots him dead with his own gun. He orders another HR officer to bring him Carter and Quinn alive.
Simmons and a large group of other HR cops set up a roadblock at the entrance to the only bridge to Manhattan where the federal building is located. Simmons notices a bloody hand print on the side of an ambulance and orders it stopped. Reese, who is in the ambulance along with Carter and Quinn, forcefully drives through the roadblock while the HR cops fire furiously at the ambulance. Fusco, who is hiding nearby, provides covering fire allowing them to escape. However, he is discovered and knocked out by Simmons.
Simmons takes Fusco to a fortune cookie factory where he brutally interrogates him, beating him and breaking his fingers. Detective William Petersen continues to interrogate Fusco for the location of a set of files which incriminate HR and are hidden in a safe deposit box. Simmons threatens to kill Fusco's son Lee if he does not cooperate. Fusco gives Simmons a fake address for the bank and when Simmons discovers that he has been deceived, Simmons orders Lee and Fusco killed while he continues to search for the right bank. However, Shaw saves Lee while Fusco kills Petersen and escapes.
After Carter delivers Quinn to the FBI and turns over her collected evidence, the FBI arrests HR with the Machine calculating that with all but Simmons in custody, HR is 98% neutralized. Carter is promoted back to detective, and Finch asks her to help release Reese, who was arrested under an alias. She meets Reese at the police precinct, reenacting the first time they met. As they reminiscence on the sidewalk outside the station house about their history together, Simmons suddenly steps from the shadows and shoots Reese and Carter. Carter fires back and wounds Simmons in the shoulder, forcing him to retreat, but she is fatally wounded. As Finch watches in horror, Reese embraces a dying Carter while a payphone, called by the Machine, continues to ring. (“The Crossing”)
Having become the most wanted man in the city following his murder of Carter, Simmons visits Seamus Yorke for a fake passport. Due to the number of people who want Simmons dead, including the Russians and Reese, the Machine generates his number while both Reese and Shaw embark on a brutal manhunt across the city for him. Reese forces Alonzo Quinn to give up Simmons escape route, but has to be taken for treatment of his injuries, rendering both Reese and Shaw unable to track down Simmons. However, Fusco finds the paper and tracks Simmons to an airfield where he cancels Simmons escape flight. Though Simmons challenges Fusco to shoot him in cold blood, Fusco instead engages in a brutal brawl with Simmons who initially has the upper hand. Fusco eventually manages to overpower Simmons, brutally breaking his arm and subduing him. Simmons orders Fusco to kill him, but Fusco tells Simmons that Carter made him a better man and he won't dishonor her memory by murdering Simmons. Instead, Fusco places Simmons under arrest and leads him into the 8th precinct to the shock of the cops stationed there.
After his arrest, Simmons is hospitalized for his injuries where he is visited by Elias. Simmons believes Elias is there to gloat about the death of HR, but Elias explains instead that he owes a debt to Carter who he liked "very much." Elias calls himself and Simmons "outliers" to civilized people and, as a result, they can do things civilized people can't. After Elias tells Simmons he sees it as his responsibility to deal with Simmons due to his murder of Carter, Simmons asks if Elias think he will be the one to kill him. Elias merely laughs and tells Simmons that he's just going to watch as his friend kills Simmons. As Elias looks on, Scarface approaches Simmons and strangles him to death with a garrote wire. (“The Devil's Share”)
- Simmons has been referred to as a detective erroneously in “Liberty”, “Razgovor”, and “Endgame”.
- His shield number on his uniform hat was 1687 until Season 2, when it was changed to 44768. Some photographs used in the show still display the old shield number.
- Simmons has worn several different precinct pins on his shirt collar; it was the 51st precinct (where Fusco originally worked) in Season 1, the 8th precinct in “Bury the Lede”, and the 20th precinct since “C.O.D.”.
- He wears 2 service ribbons: one for Meritorious Police Duty and the Liberty Breast Bar, indicating that Simmons was on the force during July 4, 1976, the American Bicentennial. However, according to his birth date, 1961, he would have only been 15 at the time, much too young to be on the force.
- Simmons has a wife and two children (one girl, one boy), as seen in “Flesh and Blood”.
- Simmons has shown himself to be skilled at close quarter combat; holding off Reese for some time in “Razgovor”. He later nearly beats Fusco before he is overpowered. (“The Devil's Share”)
- According to the file that Carl Elias gave Peter Yogorov, Simmons is from the 20th precinct, was born on 8/11/61, and weighs 210 pounds. (“Endgame”)
- Caroline Turing: Root hired HR to kill her; failed (“Firewall”)
- Cal Beecher: arranged to be killed by the Russian Mafia in a shootout under Quinn's orders (“Trojan Horse”)
- Donnie: Beecher's CI, arranged to be killed by the Russian Mafia in a shootout on Quinn's orders (“Trojan Horse”)
- Elias' lieutenant (unnamed, possibly Anthony Marconi): gunned down on Quinn's orders; survived (“God Mode”)
- Carl Elias: targeted under Quinn's orders; failed (“God Mode”)
- Genrika Zhirova: kidnapped and targeted to die; rescued by Shaw (“Razgovor”)
- John Reese: attacked during fistfight (“Razgovor”) Shot in the shoulder and leg (“The Crossing”); survived both times
- Morozov: killed because he was skimming money from HR (“Mors Praematura”)
- Sven Vanger: targeted under Quinn's orders; failed (“The Perfect Mark”)
- Natalie Boal: targeted under Quinn's orders; failed (“The Perfect Mark”)
- Hayden Price: targeted under Quinn's orders; failed (“The Perfect Mark”)
- Peter Yogorov and the entire Russian Mafia loyal to him: targeted under Quinn's orders; failed due to intervention of the FBI and Carter. (“Endgame”)
- Judge Andrew Monahan: shot once in the chest (“The Crossing”)
- Lionel Fusco - Blackmailed several times with the death of Ian Davidson, attempted to set up for the death of James Stills; foiled by Carter, (“In Extremis”) pistol-whipped unconscious and tortured for information on Carter's safe deposit box, ordered executed; failed, (“The Crossing”) engaged in a brutal brawl with. (“The Devil's Share”)
- Lee Fusco - Threatened the life of to get information, ordered executed by Lin; foiled by Shaw. (“The Crossing”)
- Joss Carter - Shot fatally in the chest in revenge for the fall of HR. (“The Crossing”)