Bolingbroke Penitentiary

Bolingbroke Penitentiary is the state prison of San Andreas in Grand Theft Auto V and Grand Theft Auto Online, located in Los Santos County.

Description
It is governed by the San Andreas State Prison Authority. The prison is located on the Los Santos County side of Route 68, just down the road from Harmony. The prison's shape is that of an octagon.

The perimeter of the prison is patrolled by the Los Santos County Sheriff and the Los Santos Police Department. There are armed San Andreas State Prison Authority officers standing near the entrances, making sure that no one attempts to break in or out.

The penitentiary seems to be inspired by the real-life Victorville Federal Prison in Victorville, California.

A speaker system is heard commonly around the prison, often insulting the prisoners. There are 41 quotes.

Events of GTA Online
In the Heists Update, during The Prison Break, the crew must storm into the prison to release a Russian prisoner named Maxim Rashkovsky. Some missions and races also take place in the prison in GTA Online.

Events of GTA V
In 2013, a prisoner has his jaw broken by "Stretch" after snitching on a fellow inmate, which lands Stretch in isolation for five days, which he completes. Stretch also gets tattoos, one of them starts with leakin' real nasty according to Stretch on his Lifeinvader page. It is during his time in Bolingbroke that Stretch forms an alliance with the Ballas and plans to sell out Franklin Clinton and Lamar Davis.

A random encounter can occur around the prison where an escaped prisoner pulls the protagonist over and then points a gun at them, and forces them to get out of their vehicle.

Demarcus Bradley, another inmate, states on his Lifeinvader page that a number of Davis High School students in the 2005 graduating class are in the prison and that he had received a friend request from the guard on his wing. He later goes blind, although it may only be temporary, after drinking prison made wine, watches his cellmate using a toothbrush he had used for other purposes and visited the prisons 'total psycho' dentist. Prison food, judging by Demarcus' comments, is of poor quality in Bolingbroke.

Events of GTA Online: The Diamond Casino Heist
During the "Prison Guard" variant of the Heist Prep: Vault Keycards mission for The Diamond Casino Heist, the player must enter the prison and kill a security guard to steal the Diamond Casino vault keycards. The player hijacks a prison bus and disguises themselves as a prison guard to gain entry without raising suspicion.

Events of GTA Online: Los Santos Tuners
During The Prison Contract, the player has to break into the prison and kill multiple sets of targets identified by Lil' Dee for double-crossing their respective gangs before rescuing Lil' Dee and taking him back to Sessanta.

Grand Theft Auto V

 * Surveying the Score

Grand Theft Auto Online

 * Bust Out
 * Criminal Records
 * Cops Capacity
 * Prison Thugz Fight

Heists

 * The Prison Break

The Diamond Casino Heist

 * Heist Prep: Vault Keycards - Prison Guard

Los Santos Tuners

 * The Prison Contract
 * Planning Work: Access Point
 * The Prison Contract

Vehicles

 * Vapid Interceptor
 * Sheriff's Cruiser
 * Park Ranger
 * Police Maverick/Air Ambulance (sometimes flying around the prison)
 * Prison Bus (Center courtyard of the prison. Extremely hard to reach and even harder to drive out)

Warning signs

 * Warning: Cameras operate in this area
 * Authorized personnel only
 * Notice: This area is protected by electronic surveillance
 * Danger: Guard dog on duty

Known Inmates

 * Merle Abrahams (Deceased)
 * Demarcus Bradley
 * Franklin Clinton (Released)
 * Unknown friend of a The Lost MC member
 * Jack Howitzer (Released)
 * Harold "Stretch" Joseph (Released/deceased)
 * Ralph Ostrowski (Determinant)
 * Maxim Rashkovsky (Escaped)
 * Many of the former students of class 2005 of Davis High School
 * Glenn Scoville (Determinant)
 * Larry Tupper (Determinant)
 * Curtis Weaver (Determinant)
 * Unnamed escapees (Escaped, can be killed).

Trivia

 * The airspace above the prison is a no-fly zone in Story Mode.
 * Shooting a firearm anywhere near the prison will cause an automatic three-star wanted level.
 * If the player is near the penitentiary while being wanted, the prison alarm will go off and guards will be warned of the player's presence, causing them to attack. This can be remedied by using the "Cops Turn Blind Eye" feature from Lester as to safely gain access inside the prison for a limited time.
 * LSPD patrol cars can be found patrolling inside the prison, despite being city police. They can also be seen patrolling outside of its borders alongside San Andreas Park Ranger.
 * Shooting a guard with a sniper rifle from the front or back will give the player a two star wanted level. If the player approaches from the back with two stars and goes up the prison's west side they will receive four stars, which is also received for punching the guard who occasionally spawns next to the barriers.
 * Inside the recreation yard, there is writing on a wall that reads, "Where water meets land and fire once spewed forth, there the infinite 8 shall stay until I return." The message is left by Merle Abrahams, who was obsessed with the number eight and had killed eight people in 1999.
 * If the player manages to get in without a wanted level (such as entering the prison in a mission where wanted levels are disabled) and get close to building 9A, they can hear blood-curdling screams coming from it.
 * When playing as Franklin or Michael, an encounter with a member of The Lost will reveal that a friend of his will be incarcerated in this prison for 5 years.
 * In Maude's Bail Bond missions, if Trevor captures any of the targets Ralph Ostrowski, Larry Tupper, Glenn Scoville or Curtis Weaver, they will be incarcerated in this prison. Since an achievement requires you to bring at least one of them alive, a gameplay trailer shows Trevor putting Ralph in Maude's trailer, and bringing them will reward the player $10,000 and killing them only gives $5,000, bringing all 4 of them alive are the canon choices.
 * Inside the guard booth at the entrance to the prison is a Burger Shot bag and cup.
 * Inside the top of the guard tower are pictures of strippers, an emergency procedure guide, a fire hydrant, a security camera and more.
 * Sometimes an Air Ambulance can be seen flying around the prison. This is most likely a glitch as the Air Ambulance is actually a re-skinned Police Maverick. Though it might be reference to prison and the fact that Air Ambulances are often used to lift wounded or seriously injured inmates to hospitals which might be a distance away.
 * Prison Guards in the towers are equipped with a default Sniper Rifle.
 * Many of the prisoners' face models are also used for models that spawn in south central Los Santos; face models extracted from default male pedestrians, and a few face models from the Original Covenant Ballas.
 * A few prisoners also use the same voice and sound files as the Families gang members, as well as the Ballas gang members, referencing the notoriety both gangs hold in crime.
 * If the player takes a taxi to the prison and skips the whole trip, the following scene will have the player killed on the spot by a sniper.
 * The prison's watertower has text on one of the sides that read "La Mesa." This is because the watertower is a reused model of the La Mesa watertower that the developers forgot to remove the text from.
 * According to Lester Crest, the company that Bolingbroke contracted to make their security keycards also contracts with the Diamond Casino.

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