Sam and Dean Winchester are constantly in trouble with the law. This started after a shape-shifter framed Dean for killing someone. The police and FBI agents hunted Sam and Dean down, only for them to escape.
The Hunt Is On.....Edit
In Season 2, Sam and Dean were arrested while on a hunt, but they saved Diana, and were set free. After that, while dealing with a shape-shifter at a bank robbery, an FBI agent known as Victor Henriksen caught them, and tried to capture them. They managed to escape by posing as SWAT officers. Later on in the second season, Sam and Dean went undercover in a prison, where a ghost was killing the inmates. They managed to escape later on.
In Season 3, Bela Talbot gave away their location to Henriksen. Henriksen planned to move them to a new facility, but had to believe Sam and Dean when demons take over the building, After the battle, Henriksen let Sam and Dean escape, but a little girl, later known as Lilith, blew up the building, killing Henriksen and everyone in it. Sam and Dean were later declared dead by the government officials.
In Season 6, Sam himself had problems with the law due to his Soulless self in Unforgiven. This caused Sam to have to hide out while Dean did the dirty work. Dean comments how it is like the good old days when the law used to chase them.
In Season 7, Sam and Dean were put on the FBI's Most Wanted list thanks to their Leviathan clones which killed people while wearing their faces. Sam and Dean managed to get rid of their clones, and the police officer there "killed" them.
Caught In The ActEditSam and Dean have been caught by the law a couple of times. The very first time was in Pilot, when Dean was leaving the motel. The police caught on when Dean kept insulting them. It's continued on in, Skin, Hook Man, The Benders, The Usual Suspects, Nightshifter, Folsom Prison Blues, Jus In Bello, Clap Your Hands If You Believe and Unforgiven. They were caught again after they were tricked by their Leviathan clones in Slash Fiction. Dean was also arrested in The Prisoner, but it was because the Styne Family ordered it to stop him from coming after them.
Arrested by the Secret ServiceEdit
In LOTUS, the Winchesters are arrested for attempting to assassinate the President of the United States, Jefferson Rooney. However, in reality they saved Rooney by exorcising Lucifer from him and sending him back to his Cage. In First Blood, they are taken to Site 94, a secret government black site by Secret Service agent Rick Sanchez who is able to identify them to his boss. Sanchez states that only himself, the arresting agents, the people at the black site and the President, who can't remember anything for the past three days, know about what happened. With the help of Billie, the Winchesters eventually manage to escape and defeat the soldiers sent after them.
After defeating Sanchez and Camp, Sam tells him the truth about what happened with the president before they walk away after threatening him. Afterwards, Mick Davies of the British Men of Letters has Arthur Ketch kill Sanchez and the people working at the black site to "tie up loose ends", preventing the government from chasing the Winchesters again as everyone who knew they were alive in the government was killed.
Other Criminal ActsEdit
- Credit card fraud
- Breaking and entering
- Impersonation (FBI, CIA, Homeland Security, CDC, etc.)
- Grave desecration
- Breaking out of Jail
- Assaulting An Officer
- Desecration of corpses
- Grand Theft Auto (stealing a car)
- Mass Murder
Notably there have been exceptions to the Winchesters bad experiences with the law. In The Benders, Dean worked with Deputy Kathleen Hudak to rescue Sam and capture the Bender family. While the deputy figured out Dean wasn't who he said he was, she continued to work with him in hopes of finding out what happened to her missing brother. The three captured the Benders and the deputy let them go afterwards despite knowing the authorities would want to talk to them. The biggest exception however is with Sheriff Jody Mills of Sioux Falls, South Dakota. While at first she arrested them and refused to let them deal with a zombie situation in Dead Men Don't Wear Plaid, Jody quickly became their friend and ally, helping them deal with the zombies and helping the Winchesters and Bobby on cases. In Rock and a Hard Place, Alex Annie Alexis Ann and Hibbing 911, Jody called the Winchesters in on cases she recognized was their kind of thing and helped them, even covering for them when faced with other law enforcement officers. Jody subsequently became a hunter in her own right and a prominent ally of the Winchesters, taking cases of her own without needing to call Sam and Dean every time. On multiple occasions, such as when Jack vanished, the Winchesters would call Jody to use her police connections to help them in the search. In Jack's case, this turned out to be extremely useful as Jody's APB found a witness Jack placing Jack at Derek Swan's death and led the Winchesters to him.
They also made an ally in Sherriff Donna Hanscum in Hibbing 911, another cop they'd worked a previous case with though she was unaware of their identity at the time. In the original case in The Purge, Donna had accidentally blown their cover while roofied and was given a cover story after the case was over. Donna decided to become a hunter after taking down a vampire on her own and becomes a frequent friend and ally of the Winchesters along with Jody Mills.
A strange exception was in Ask Jeeves when during a murder investigation, Sam and Dean were using their real names and the detective investigating called them by it and never seemed to realize who they really were despite "their" well-publicized murder spree a few years earlier.
In Tombstone, Dean teamed up with Sergeant Joe Phillips to take down a ghoul who killed the man's nephew. At the end of the hunt, Dean helped Phillips kill the ghoul and get his revenge. The next day, Phillips questioned him on the events and Dean told him a cover story that the ghoul killed the victims and the security guard that had been killed by Jack. Phillips agreed to the story and to the fact that the Winchesters would have officially never been there.
In Breakdown, the Winchesters are called by Sheriff Donna Hanscum to help her and her boyfriend, Officer Doug Stover find Donna's niece Wendy Hanscum who has been kidnapped. Though all signs point to a human villain, the Winchesters agree to help and work alongside FBI agent Terrance Clegg, Donna and Doug who is unaware of Donna's hunting activities. The Winchesters uncover an auction for monsters and are forced to tell Doug the truth, particularly after he gets turned into a vampire. Dean and Donna are able to cure Doug while Clegg turns out to be the bad guy and is killed by Dean to protect Sam. After the case is over, Doug is terrified by what he's seen and breaks up with Donna.
In Damaged Goods, after their mother is kidnapped by Nick, Donna has her deputies search for his stolen van. Once they find it via traffic cameras, Donna acts as a police escort for the Winchesters, leading the Impala with her lights and sirens to the storage facility where Mary has her lock-up. After Abraxas is killed, Donna arrests Nick for his murder spree which was revealed to her when she ran his fingerprints.
During Don't Go In The Woods, the brothers meet Mason Romero who orders to stay away from the woods after a mysterious death. Later on, they confront him and he reveals details of the Kohonta and they reveal the supernatural to him, as well as reasons not to expose its existence to the public. They also help him save his son from the monster and allow him to kill it.
On some occasions, the Winchesters have been able to use their law enforcement connections to their advantage such as having Jody Mills put out an APB on Jack to help search for him, something that was successful. On another occasion, as seen in The Gamblers, Dean used one of his FBI aliases to open an FBI file on Jack which helped to find him after Jack's resurrection.
- In Crossroad Blues, Sam discovers that while Dean is wanted following the incident in Baltimore in The Usual Suspects, Sam is apparently not wanted at all in connection to Dean's supposed crimes, not even as an accomplice.
- After Dean's arrest, running his fingerprints come back with over a dozen possible hits in at least three different states when run through the AFIS database. This means that Dean's fingerprints tie him to potentially a dozen different crimes at the time of The Usual Suspects. These crimes are likely what Detective Peter Sheridan was reciting to Dean during the initial interrogation in The Usual Suspects. It also suggests that Dean's never been fingerprinted before that episode as its only when he's arrested in Baltimore and his fingerprints are run there that he's tied to those crimes.
- Given the amount of time that has passed since much of the Winchesters crimes were committed, the statute of limitations has likely expired on them. This means that even if the Winchesters are caught, they can't be charged with many of their crimes as too long has passed. Only the charges with no statute of limitations such as murder would they actually be able to be charged with. The others, including likely the armed robbery from Nightshifter, have happened too long ago. The only charges that would definitely be chargeable are the murder the Serial Killer Shapeshifter committed in Skin that Dean is wanted for and the murder spree the Leviathan duplicates went on in Slash Fiction.