Pike was a former money launderer for a Miami drug cartel. Pike stole the money and ran with it, causing the cartel to want him dead. Raylan also pursued him actually having him captured at a bar in Brownsville, Raylan said that Pike could either spend a short life on the run from bad guys like Tommy Bucks, or he could get him into WitSec and get him a new identity. Pike gave him his word, and Raylan left him watching "Rudolph the Red-Nosed Reindeer" to get ice cream, and ended up letting Pike run off again. It's also because of watching that program he was inspired to be a dentist. Pike got his dentist license from Panama while on the run from the cops and the cartel, and ended up relocating to Los Angeles, California where he began doing dental work as "Peter Oldman" in an attempt to start at a new life. Pike managed to lay low in Los Angeles until an unruly client named Mr. Ferguson launched in a tirade against Pike's receptionist, Mindy, causing Pike to assault him in a parking lot and the event being caught by a security camera and aired on TV, easily helping the Marshals, police, and the mob get back on the pursuit of Pike.
Pike is first seen in the episode Long in the Tooth. He is seen working on the teeth of a little girl, who is Mrs. Pena's daughter. Mrs. Pena pays Pike in tamales since she doesn't have to money to pay for the operation. After she leaves, Mr. Ferguson soon comes in complaining about Mindy due to the fact his insurance company doesn't cover the dental procedures he had been receiving. Ferguson insults Pike's staff as well as his office being dirty, saying for him to "get some Pine Sol". Pike, in a fit of anger, assaults the man in a parking lot, cornering him in his car and rips out two of his back molars. Pike is no longer laying low because the assault was caught on a security camera and aired on TV as mentioned before, so now Raylan as well as the cartel know where Pike is located.
Roland and Mindy then decide to flee to Mexico together, from there they will go to Belize and start a new life, as well as open up a new dental business. Roland initially lies to Mindy and tells her that the police are after him cause of "unpaid parking tickets", but ends up telling her the truth in a supermarket. Roland then decidees to steal a car while Mindy trades the gold in for money, but gets busted by an old war veteran named Mr. Jones, who calls him out for it, but ends up swapping cars with Roland after seeing how "sweet" of a ride Roland had, which easily gets Roland's car off their hands. Raylan calls Roland and tells him, "You know what's going to happen to you and Ms. Springer if the bad guys find you before I do?" Roland knows this and ditches the phone in the window of a passing by truck.
Meanwhile, two of the cartel members, Joe and Frank are spying on Raylan, and end up calling a hit down in Miami on Roland and Raylan both, but also they have a hired sniper to wait down in Mexico to kill Roland if they reach the border.
Roland learns that his old associate, Hector, no longer makes fake passports and has retired to run a taco stand. Hector does tell them that they can hire a "coyote", someone that they can pay to get them through into Mexico. Roland goes to his loyal clients over the years, the Penas and says "Mindy and me need to get into Mexico." Mrs. Pena is offended by the comments, taking them as racist, and refuses to help them due to the fact Roland is all over the news and is a fugitive now, she leaves to go in a back room to call 911. Her father, Don Jaime, agrees to set them up with a "coyote". The old man does entrust in Raylan the location of where Roland and Mindy are going to meet with the "coyote" after realizing that their beloved dentist could end up killed.
Roland and Mindy manage to make it to the meeting with their "coyote", who gives them the supplies they need and walks them to a rest point. The "coyote" demands TWICE their pay now, which they don't have. To compensate, the "coyote" attempts to rape Mindy, but Roland intervenes. Roland goes to grab the "coyote", but ends up stabbed with a knife in the stomach. Roland then grabs a huge rock from the ground, hitting the "coyote" in the back of the head with it, and in his head several times before killing him. Roland freaks out over this saying that he was a good person, but was involved with bad people, and knew he was capable of doing bad things (such as killing the "coyote" and assaulting Mr. Ferguson).
Raylan catches up to Mindy and Roland, but immediately after doing so, they are shot at by the hired sniper. Mindy and Raylan take refuge behind a van, while Roland ducks behind a sand pile he is on. Roland tells Raylan that dentistry is his calling, and knows if he turns himself into the Marshals for witness protection, that he will NO longer be able to do that. Roland stands up despite protest from Raylan not to, and ends up being shot and killed by the sniper.
- Mindy Springer: Receptionist, girlfriend
- Mrs. Pena: Client
- Mr. Ferguson: Client, Assault Victim
- Coyote: Guide, Murder Victim
- Joe: Would be assassin (Killed by Raylan)
- Frank: Would be assassin (Killed by Raylan)
- Unknown Sniper: Murderer
- "I love you Mindy!" - Final words before being killed ("Long in the Tooth").
- "Consider me the repo man!" - ("Long in the Tooth")
|Season one appearances|
|Fire in the Hole||Riverbrook||Fixer||Long in the Tooth||The Lord of War and Thunder|
|The Collection||Blind Spot||Blowback||Hatless||The Hammer|
|Veterans||Fathers and Sons||Bulletville|