"Long in the Tooth"
Season 1, Episode 4
Air date April 6, 2010
Written by Chris Provenzano
Directed by Adam Arkin
U.S. Viewers 2.10 million
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"Long in the Tooth" is the fourth episode of the first season, and the fourth episode in the series overall. It was written by executive story editor Chris Provenzano and directed by Adam Arkin. It first aired on April 6, 2010.

Raylan pursues an old target Roland Pike, now living as a dentist named Dr. Peter Oldman, after he appears on television. Raylan is competing with a Miami crime boss to locate the fugitive. Roland attempts to escape across the border into Mexico with his girlfriend, Mindy. They sell a stash of dental gold to raise funds and pay a coyote to guide them. Raylan faces off with the cartel gun thugs who have been hired to track Roland. They draw their weapons and he kills them both. The coyote attempts to rape Mindy during the crossing and Roland kills him, immediately regretting the violence. Raylan tracks the pair into the desert but when he arrives they are attacked by a sniper laying in wait. Roland stands up and is shot and killed before Raylan can get him to safety.



Raylan and the mob compete to capture a fugitive, Roland Pike, racing to the Mexican border.


The episode begins in Los Angeles, showing the dentist office of Dr. Peter Oldman, who is taking care of a young child's teeth.

The child's mother, Mrs. Peña, pays Dr. Oldman in the form of homemade tamales since she doesn't have the money. As Mrs. Peña goes to leave, another client, Mr. Ferguson, comes in and launches a tirade against Oldman's receptionist, Mindy Springer, because his insurance company doesn't cover the elective procedures he has been receiving. Mr. Ferguson then insults Mindy as well as his building that he works in, telling him to get some Pine Sol.

In a fit of rage, Dr. Oldman traps Mr. Ferguson in his car, threatening him with a needle full of drain cleaner fluid if he doesn't comply. Dr. Oldman says he is going to claim what is his, and proceeds to rip out two of Mr. Ferguson's back molars minus anesthesia, leaving Mr. Ferguson screaming in pain as Oldman walks away from the car.

Meanwhile, at the Kentucky marshals' office, Raylan quickly identifies Dr. Oldman as Roland Pike, a criminal Raylan has been pursuing for years. Raylan had arrested him in Brownsville, Texas, and planned to put him in witness protection for informing on the mob, but he managed to escape. Roland had said he wanted to finish watching a children's Christmas special on TV and Raylan, mistakenly trusting him, went next door to buy some ice cream while Roland fled. Much to Raylan's displeasure, Art says that Rachel is not only going to California with him, she is taking lead on the case.

In Los Angeles, Roland watches from a distance as news vans and law enforcement converge outside his office, and spots Raylan arriving. Mindy leaves the dentist office with the tray of tamales, offering some to the marshals, who decline. After she leaves, they discover that dental gold is missing.

Roland and Mindy, who is also his girlfriend, plan to flee to Mexico in order to get away from the cops. Roland lies to Mindy telling her that the cops are after him because of unpaid parking tickets, and they are going to trade in gold to get cash in order to have the money to cross the Mexican border to head into Belize to start a new life and a new dentist company.

At a store, Roland hatches a plan for Mindy to trade the gold in for cash while he goes to look for a car to steal. Mindy confronts Roland, knowing that he wouldn't have federal agents after him for unpaid parking tickets. Roland then confesses that his real name is not Peter Oldman and that the federal agents are after him because he used to be a money launderer for a drug cartel, but he stole some of their money and ran with it. Mindy tells him to never lie to her anymore.

Roland goes into a parking lot to steal a car, but just as he is about to steal one, a war veteran named Mr. Jones spots him and tells him he knows he is going to steal the car because he saw the real car that he drove up in. Jones manages to fluke Roland by telling him to say his plate number without looking. Jones then calls Roland's car "a sweet ride" and they swap cars, which gets Roland's car off of his back.

Meanwhile, one of Mindy's friends, Shawni Burnett, tells the marshals that she saw Roland on the news and is concerned about Mindy. Raylan then calls Mindy using Shawni's phone and talks to Roland. Roland then tells Raylan that he suspects that the call is being traced, but not before Raylan tells him that he saw him on TV as well as the whole Marshal Service, Shawni, and his friends in Miami, and asks him if he knows what the bad guys will do to him if they reach him before Raylan does. Roland then tosses the cell phone into a truck that's passing by. Rachel offers to track Roland, but Raylan tells her that he's already dumped the phone. In the meantime, Roland is furious because Mindy got ripped off of the gold she pawned, only getting $4,700 for it when there was at least $10,000 of gold.

Joe and Frank have been watching Raylan, who they recognize as killing Tommy Bucks, as he talks to the police. Joe calls his associates in Miami to let them know Raylan is there, and saying that he must be looking for Roland just like they are, and tells them to call him back and make a deal.

The police pull over Jones, who is driving Roland's car. Jones proceeds to insult the two officers in the process. Meanwhile, Roland and Mindy go up to a taco stand worker named Hector in order to get fake passports from him, but they learn that Hector has "retired" because of changes after 9/11. Hector tells them that they need to find a "coyote," someone who helps smuggle people across the border. Meanwhile, Raylan and Rachel are still trying to get answers out of Jones, but Jones still refuses to say anything.

Mindy and Roland then show up at Mrs. Peña's house to ask for her help getting to Mexico, but she has seen what he did on the news and refuses to help. She is insulted that he would assume she knows a coyote because she is Mexican. However, Mrs. Peña's father, Don Jaime, offers to help them because they have been so good to their family over the years. Mrs. Peña, however, goes into a back room to call the police to tell them that Roland is in their house.

Don tells the cops that he sent them to meet up with a coyote near the Home Depot off Highway 805. Raylan talks to Don and tells him he suspects Don lied out of loyalty to Roland. He tells Don that bad men will certainly find Roland and Mindy and kill them, but that the marshals will make sure that doesn't happen if they find them first.

Roland and Mindy then meet up with their coyote, who hands them the stuff they will need, and tells them they will go halfway, rest and then cross at night. Raylan manages to find their car, but Frank and Joe show up as well. Raylan tells them if they walk any further that he will shoot them both. Joe tells him that he has something important to tell him but doesn't drop his gun, and Raylan shoots him in the stomach. Frank tries to fake out Raylan by acting as if he's going to throw his gun away, but tries to aim at Raylan and is quickly shot. The dying Joe tells Raylan that he called out a hit on Roland in Mexico and if he's not dead now, he will be soon.

Roland, Mindy and the coyote end up reaching their resting spot. The coyote demands his pay or else Roland and Mindy have to walk the rest of the way themselves. However, the coyote ups his price to $2,500 each ($5,000), but Roland only has $2,500. To make up for the loss, the coyote attempts to rape Mindy but Roland tells him not to touch her. Roland grabs the coyote, but he pulls out a knife and stabs Roland in the stomach.

The coyote continues his attempt to rape Mindy, but Roland picks up a huge rock and hits the coyote in the back of the head with it several times, killing him. Roland, after seeing what he did, gets upset and says that he never was a bad person, he just worked for bad people, but knew he was capable of doing wrong to people. Roland tells Mindy to stay away from him and says that Mindy doesn't know who he is, but she says she's watched him for five years as a dentist and they continue on to Belize.

Raylan manages to locate Mindy and Roland, but during the talk, Roland is shot at by a sniper. Roland then tells him what inspired him to be a dentist was Hermey the Misfit Elf from the Rudolph, the Red-Nosed Reindeer special that he was watching when Raylan first arrested him. As a child, Roland had been inspired by Hermey, who makes toys but wants to be a dentist, and got books and little tools about dentistry. Roland forgot about it, but when he saw it again in Brownsville, he was sure it was God telling him he was meant to be a dentist.

Roland eventually accepts his fate and stands up, getting shot and killed by the sniper. The sniper then flees the scene, while Mindy runs up to the body crying.

At the end of the episode, Raylan is shown sleeping in the car with Rachel, who proceeds to take his cowboy hat to try it on (A reference to earlier in the episode when Raylan offered Rachel to try on his cowboy hat). Raylan asks her if it fits, to which she simply replies, "No." Raylan reaches out his hand for the hat, then puts it back over his eyes, and goes back to sleep.


First AppearancesEdit

  1. Roland Pike - Former money launderer for the Miami drug cartel, who stole their money and ran with it. 
  2. Mindy Springer - Pike's receptionist and lover who agrees to run away with him.
  3. Mr. Jones - Ornery war veteran who exchanges cars with Pike.


  1. Frank - Assassin for the Miami drug cartel sent to look for Pike. Shot by Raylan Givens.
  2. Joe - Assassin for the Miami drug cartel sent to look for Pike. Shot by Raylan.
  3. Coyote - Bludgeoned to death with a rock by Pike.
  4. Roland Pike - Shot by a cartel sniper.



Starring cast

Guest starring



External linksEdit