For decades, dating back to the Prohibition Era, The Bennetts and the Givens have been feuding and now Dickie's family are pot dealers. Dickie still limps because of a teenage altercation involving Raylan.
They were playing high school baseball; Dickie (pitching for the opposition) knocked Raylan down with a brushback pitch after Raylan hit successfully in his first two at-bats. In the ensuing melee Dickie was about to put his cleats in Raylan's face, so Raylan struck Dickie with his bat on the side of the kneecap, making it "my third hit of the day". Ironically enough, Raylan also shot Dickie in his good leg in "Coalition", when he attempted to draw his gun on Raylan. Dickie is also the last remaining member of the Bennett family who is still alive following the death of his brothers Coover and Doyle and his mother Mags.
At the start of season 2, Dickie and his brother Coover run their family's marijuana distribution, while often smoking their own product. It becomes apparent that neither are held in high regard by their mother, Mags. Throughout the season they are perpetually in trouble with Mags for their mistakes, like hiring a sex offender whose capture brings them under the Marshals' attention, and for having a bus full of drugs hijacked, leading to their brother Doyle having to kill the two thugs they sent to hijack it to cover up their mistake. Dickie's role does not become bigger until Coover is killed by Raylan, an event that his family blames him for. As a result, Dickie is given control over the pot trade by his mother, but is told he will not receive anything from their deal with Black Pike. He is also told to allow Boyd Crowder to extend into any other criminal activity, an order he decides not to follow.
Dickie ends up being robbed of his weed and all his money by Boyd Crower, Arlo, and Devil in the episode "Full Commitment". However, Dickie notices that one of the men is Arlo based on the fact that he was limping. Dickie then decides, along with Jed, that they are going to kill Arlo, but when they get there, they meet Helen with a shotgun (Arlo was out with Boyd, Johnny, and Devil when this was all going on.) Helen manages to shoot Jed, but ends up being killed by Dickie. A furious Raylan has Dickie handcuffed and on his knees in the woods, holding a gun to his head. However, he remembers that Helen did not want him to be a cold blooded killer and even paid him to leave Harlan so that he didn't end up like Arlo. Raylan simply knocks him unconscious with his gun and Dickie ends up arrested. Dickie winds up being released from jail in the same episode Reckoning due to the fact an old lady visited him in prison and Jed recanted everything that he confessed to Raylan.
In the season 2 finale, Bloody Harlan, Dickie goes into Mags's store, furious that she would negotiate with a Crowder. All of the money that had been stolen from Dickie, Boyd now offered to Mags. Later on that day, Dickie and some of his boys show up at Ava's place and begin to open fire. Dickie pops up in the kitchen and shoots Ava in the chest before she can shoot him and leaves. Furious, Boyd makes a call which now puts the price on Dickie's head even higher because of this. Dickie then manages to show up at Wade's place, knocking Raylan unconscious. Whenever Raylan wakes up, Dickie proceeds to hit Raylan twice with the bat, the first in his torso and the second in his shouler. Before he can hit him a third time, Boyd shows up with a gun and forces Dickie to untie Raylan. Raylan goes to leave, but Dickie, knowing that he is going to be killed by Boyd, pleads with Raylan to take him along because he knows Loretta's whereabouts and because Doyle has his men in that area. Dickie then finds himself with a gun to his head by Raylan, demanding that he see Loretta. After Loretta shoots Mags in the leg, the goons outside get scared and open fire on Raylan and Dickie, hitting Raylan in the leg and causing Dickie to jump into the front seat panicking. Raylan reveals to Mags at the end of the episode that Doyle is dead and Dickie has been placed under arrest.
Dickie's first appearance in this season is at the end of the Season 3 premiere, "The Gunfighter". Dickie and Dewey Crowe are discussing tattoos while waiting in line in order to make a phone call while in prison. However, their conversation ends up interrupted when they both see Boyd entering the prison. Dewey simply asks, "What the hell's he doing here?". Boyd looks at them both by walking by, and Dickie and Dewey both watch Boyd leave to go to his cell.
In "Cut Ties", Dickie is moved to solitary confinement (possibly at Raylan's request in order to keep Boyd away from him). Unbeknownst to Raylan, Boyd has bribed a guard named Ash Murphy to get to Dickie in solitary confinement. Boyd pins Dickie against the wall of his cell and holds a razorblade to his neck. He demands to know where all of Mags' stashed money is. Dickie reveals that Ellstin Limehouse is holding the money and claims that he will not give it to anyone but Dickie. Boyd is released soon afterwards.
Dickie is confronted by Murphy in "Harlan Roulette". Murphy informs Dickie that he overheard his admission to Boyd and demands the money. Dickie laughs it off and says that there was no money, claiming that it was a ruse to keep Boyd from killing him. Murphy doesn't believe him and threatens to make Dickie's life in prison disastrous. Dickie tells him if there was any money, which there isn't, that he cannot access it while in prison.
In "The Devil You Know", Dickie and Dewey are badly assaulted in a large prison fight organized by Murphy. Murphy brings the two to Lance to treat them. Murphy is furious that Dewey got in on the plan (Dewey had jumped in to back up Dickie), but now he is a liability. The two are transported in a coroner's van by Edward Fowler, where is to meet up with Murphy. Murphy kills Fowler due to the fact the Marshals have a lead on him. Murphy wakes up Dickie, and tells him that they are going to head to Limehouse's place, while Lance takes Dewey to a motel. However, the cops have a checkpoint at the bridge into Limehouse's place, so the two are unable to go through to get the money. Murphy takes the two back to the hotel, where Murphy forces Dickie to call Limehouse and organize a meeting where they will get the money. Dickie, Dewey, Lance. Combs, and Junior head out to Mags's old store after witness Ash being run over by Raylan. Combs and Junior hold Dickie at gunpoint as they walk through the store. Junior rushes Dickie to find the money, despite the persistence by Dickie. Eventually, Dickie pulls out a cooler from the wall, surprising Junior. However, Dickie hestitates from opening the box in order to stall time for Limehouse to arrive, and Combs suggests the possibility that Dickie could have a gun in the cooler. Dickie eventually does open it and says "holy shit". Junior asks what, and he is shot and killed by Limehouse who was hiding out in the room. Combs makes a run for it, and Errol shoots and kills him. Dickie realizes there is only $46,313 in the cooler, despite the $3,000,000 he expected. Limehouse tells him that Mags spent most of it buying the Black Pike properties. Dickie refuses to accept the cash, but asks Limehouse for a shotgun instead. Limehouse orders the henchman to unload his gun and give it to him. Limehouse asks Dickie if he is good with this deal, and Dickie laughs it off in disbelief. Raylan soon comes up to find Dickie firing off random shots from the gun, and sees the dead bodies of Combs and Junior on the ground. Dickie tells Raylan that he surrenders, and to be very clear that he was the victim.
In "Guy Walks Into a Bar", Dickie is on the verge of being pardoned, much to the displeasure of Raylan (who still holds hostility towards him for his unjust killing of Helen). Raylan ultimately has no choice but to testify against Dickie himself since the people that know of Dickie's crimes are either dead, incarcerated, or less than responsive with him. Dickie starts by pleaing to the courts that he is a changed man, but nobody believes him. Raylan stands up and says "We all know what's going to happen if Dickie Bennett is released," "More blood will be spilled. Either his or someone else's." Givens then calls Dickie a "thug" before having a change of course and deciding to give Dickie pardon. Raylan believes that freeing Dickie keeps the AUSA from receiving a lawsuit plus it gives them a lead on Mags's stashed money.
In "Measures", Errol meets up with him shortly after his release from Trumbull. Errol once again offers him the cooler full of money, but Dickie learns it contains the same amount of money from Limehouse's previous offer. Dickie then calls Limehouse's character into question for stealing Mag Bennett's money, and Dickie's inheritance. That talk earns a slap from Erroll, who nevertheless offers Dickie a ride. Dickie refuses and takes a cab instead. Later, he meets up with Rodney Dunham at Mags's old store. Dickie proposes getting back his family's $3 million from Limehouse. Rodney likes the idea, but Dickie has to locate the cash first. Not long after their conversation, Rodney and his henchman are busted by Rachel Brooks and Tim Gutterson. Dickie soon visits Ellen May, who warns him that Ava is now running the place. Dickie doesn't care and asks Ellen May, who has spent time hiding out at Limehouse's compound, where Limehouse hides his money. The prostitute tells Dickie that the money is buried under the church. Dickie disbelieves her until she says that Trixie, a fellow prostitute, also witnessed the same thing. She asks Dickie to promise to make her queen if he ends up running things. Dickie returns to Rodney with good news: Limehouse hides his money underneath his church. Outside, Gutterson and Brooks listen in on the conversation via Dunham's cell' 'phone. Dickie, in the dark as usual, is shocked when Rodney declares that he has changed his mind and won't be helping Dickie reclaim his money from Limehouse, after all. Dunham picks up his cell' 'phone and as he exits the store, tells the listening Deputy Marshals that what they've overhead should be enough for their purposes. Errol soon meets up with Dickie at the store, as per requested by Dickie to deliver the money in the cooler. However, the transaction is interrupted by Rachel and Tim. Back at the Bennett store, Dickie and Errol strike a deal to have Errol betray Limehouse in exchange cut of Dickie's money, which isn't buried under the church at all. The two men need back up but Errol reveals it cannot be anyone from Noble's Holler because they are too intimidated to turn against Limehouse. Errol suggests someone with particular skills and suggests that they partner up with Boyd Crowder.
In "Coalition", a reluctant Dickie and Errol visit Boyd at Johnny Crowder's bar in order to recruit Boyd's services in locating Mags's money. Boyd (who holds a grudge against Dickie for shooting Ava) grabs him and drags him in the back room towards his office, putting a plastic bag over his head and punching him several times. Errol begs Boyd to stop, because there is more than $3,000,000 and the only people that can help Boyd locate the money are Dickie and Errol. Boyd reluctantly stops after Ava begs him to let them hear out the plan. Dickie very unwisely starts to demand a 70-30 split in his favor when Boyd pulls a pair of guns. Boyd knows that Errol and Limehouse are trying to set him up and isn't concerned with Dickie just yet. Boyd leaves and orders Johnny to watch over Dickie and Errol. Dickie tosses a cue ball at Johnny and while he is distracted trying to pick it up, Dickie knocks Johnny unconscious before pulling a gun on Errol demanding to know where Mags's money is stashed. As it turns out, Loretta had been the holder of Mags's money. Dickie and Errol take off to go to Loretta's foster home and Dickie forces Errol at gunpoint to shut himself up in the trunk. Dickie walks in the door to find Raylan sitting in a chair waiting for him (Raylan received a lead on the money from Limehouse himself). But he doesn't order Dickie to drop his lowered weapon. "I'm coming to pay my respects to my baby adopted sister!" Dickie says. Explains Givens: "The problem is you keep thinking you're tough... but you're just stupid." Dickie refuses to go back to prison and realizing his hopeless situation and goaded by Givens' stream of insults, tries to pull on the Marshal, who fires a single round, sending Dickie to the ground in pain where Limehouse unknowingly is sitting in the backyard.
In "Weight", Dewey visits Dickie (who is now bound to a wheelchair following being shot in his good leg by Raylan) at Trumbull, asking for a dealer to go to with his stolen heroin. Raylan shows up at Trumbull to talk to Dickie, who knows Dewey's whereabouts, but wants a prison transfer in exchange for the info, but Raylan says no. Dickie and Raylan exchange barbs, until Raylan realizes he doesn't need Dickie's help to track Dewey after all because whoever Dewey visits will just tip off Boyd and the Crowes.
- Mags Bennett: Mother, deceased
- Pervis Bennett: Father, deceased
- Doyle Bennett: Older brother, deceased
- Coover Bennett: Younger brother, deceased
- Loretta McCready: Associate, unofficial "sister"
- Jed Berwind: Criminal associate
- Ellstin Limehouse: Associate
- Dewey Crowe: Associate, fellow hostage
- Wade Messer: Criminal associate, deceased
- Errol: Criminal associate
- Rodney Dunham: Business associate, deceased
- Ava Crowder: Shooting victim
- Ash Murphy: Prison guard, deceaed
- Lance: Prison medic, deceased
- Combs: Captor, deceased
- Junior: Captor, deceased
- Baz: Criminal associate
- Logan: Criminal associate
- Helen Givens: Wife of Arlo Givens and step-mother of Raylan Givens
- "For what it's worth, never knew he was a molester."
- "Now am I right or am I damn right?"
- "DON'T YOU HURT MY BROTHER, RAYLAN!"
- "To be very clear, I am the victim here."
|Season two appearances|
|The Moonshine War||The Life Inside||The I of the Storm||For Blood or Money||Cottonmouth|
|Blaze of Glory||Save My Love||The Spoil||Brother's Keeper||Debts and Accounts|
|Full Commitment||Reckoning||Bloody Harlan|
|Season three appearances|
|The Gunfighter||Cut Ties||Harlan Roulette||The Devil You Know||Thick as Mud|
|When the Guns Come Out||The Man Behind The Curtain||Watching the Detectives||Loose Ends||Guy Walks Into a Bar|
|Season five appearances|
|A Murder of Crowes||The Kids Aren't All Right||Good Intentions||Over the Mountain||Shot All to Hell|
|Kill the Messenger||Raw Deal||Whistle Past the Graveyard||Wrong Roads||Weight|