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.....
In season 2, Sam and Dean were arrested while on a hunt (The Usual Suspects S2 E7), but they saved Diana, and were set free. After that, while dealing with a shape-shifter at a bank robbery (Nightshifter), 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 (Folsom Prison Blues), 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 office there "killed" them.
Caught In The Act
Dean handcuffed to a police car
Sam 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 him.
Arrested by the Secret Service
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, Sam tells him the truth about what happened before they walk away. 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 Acts
- 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
- Arson
- Grand Theft Auto (Stealing a car)
- Kidnapping
- Murder
- Mass Murder
Exceptions
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. 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.
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.