"Rupert" redirects here. For the businessman, see Rupert Snow. For the member of British royalty, see Prince Rupert.
Rupert Winchester
Biographical information
Full name Rupert Winchester
Gender Male
Status Alive
Birth 1957
Nationality Flag of United Kingdom British
Residence Grimsborough, U.S.
Oxford, England, United Kingdom (formerly)
Affiliation(s) Grimsborough Police Department
Oxford University (formerly)
Grimsborough Police Department
Rank Lab Chief
Game information
Appears in Criminal Case
First appeared Case #1: Snake in the Grass (s5)
Wiki-what? Oh yes, that dreadful thing! Why people stopped using encyclopedias, I'll never know.
—Rupert Winchester

Rupert Winchester is a main character featured in Season 5 of Criminal Case, where he serves as the Lab Chief of the Grimsborough Police Department.


Hailing from England and 61 years of age, Rupert wears glasses over his green eyes and has gray hair that is combed towards the left. He wears a white lab coat over his brown vest with two front pockets, the left one holding a pencil and a pen. The lab coat is over a white collared shirt and black necktie.

Rupert studied at Oxford University, attributing to his lack of assimilation with American customs. He values proper manners and scientific accuracy and likes a cup of tea and a good book. Per his suspect appearance in Game Over, it is known that Rupert uses a Rolington typewriter.

Height 6'1"
Age 61
Weight 159 lbs
Eyes green
Blood O+

Events of Criminal Case

Gone Pear-Shaped

After Amir and the player got a ticket to DreamLife's launch party for their new VR system, they went to Rupert in order to convince him to join them in attending the party. At first, Rupert resisted, saying that he did not understand the appeal to virtual reality but conceded in order to see what VR was all about. He joined Amir and the player in the launch party, where DreamLife launched DreamLife VR, a game where players could discover a world tailored to their very dreams. After the launch, Rupert said that people could do impressive things with computers.

Murder on the Dance Floor

After the player arrested Robyn Ash for the murder of Kalua Kaboom, Amir told them that Rupert had not shown up for their meeting at the Riverside Market. The two found Rupert's to-do list in the market, which (per Gabriel) proved that Rupert was busy playing DreamLife's virtual reality game. With Ziggy Sparks's help, the two traced Rupert back to the lab. When they talked to him, Rupert apologized, saying that he forgot that they had a meeting. The two also returned some change to him for a record he had to buy for the game. Rupert said that he was rather taken by the virtual reality game and that he was particularly keen to complete the latest challenge that would allow him to have afternoon tea with the Queen. Amir told him that playing the game was fine, as long as he remembered that it was just a fantasy and that people in real life could be worried about him.

Downward-Facing Dead

Rupert did not appear at all during the investigation into Scott Morris's murder, which Amir attributed to his playing the VR game. After Scott's killer was arrested, Amir and the player tracked Rupert down, eventually finding his headset. Per Cathy's analysis of the headset, the game had a feature wherein playing it for 4 hours would unlock a special game mode that freezes the light at a particular level, making the player unaware of the passage of time.

Rupert eventually turned up at the station, furious about losing his headset. After the team told him of the light feature, he denied that the game would have any bugs and angrily insisted that he could quit the game anytime before leaving the station.

Game Over

Jones and the player found Rupert's ticket to the tech convention where Juniper was murdered, prompting them to treat him as a suspect. Rupert told the team that he was distraught over Juniper's death, as he had gotten to know her from playing the VR game. He then said that Juniper was not virtual to him and that he had to leave for a tea date with her in the VR game.

Later, the team found out Rupert sent texts to the real-life Juniper inviting her to a tea date, but Juniper rejected the date. Rupert told the team that given his connection with the virtual Juniper, he thought that he would get along with the real Juniper. However, upon receiving Juniper's message, he realized that she was not a sophisticated woman at all, so he stopped pursuing her.

Rupert was found to be innocent when Juniper's brother, Tim Cooper, was found guilty of the murder. The team talked to Rupert afterward, however, to try to get him to quit the game using the game ending that DreamLife had created and Gabriel's five-step program in quitting the game. After Rupert tried it out, he told Amir that he was going to wean himself out of the game.


As the Lab Chief of the Grimsborough Police Department, Rupert has the responsibility of taking care of all the necessary physical, biological, and/or clinical analyses, and to inform the team of such results after a certain amount of time or a speed-up process using Criminal Case Cash. His task-wait rates vary depending on the difficulty of the task, but they all cost 1 Criminal Case Cash per 30 minutes.

Case #1: Snake in the Grass

  • Sleeping Snake (12:00:00)
  • Strange Flakes (09:00:00)

Case #2: Hell is Other People

  • Bloody Sunglasses (12:00:00)
  • Bloody Handkerchief (09:00:00)
  • Beige Fibers (15:00:00)

Case #3: The Saddest of All Keys

  • Bloody Blister Pack (03:00:00)
  • Toothbrush (09:00:00)
  • Blood (09:00:00)

Case #4: Cross My Heart

  • Strange Bracelet (09:00:00)

Case #5: Too Cruel for School

  • Acid Bottle (09:00:00)
  • Grass Sample (03:00:00)
  • Computer Cable (09:00:00)

Case #6: Hear My Cry

  • Saliva (12:00:00)
  • Gritty Liquid (09:00:00)
  • Amlodipine Box (06:00:00)

Case #7: Flatline

  • Blue Liquid (03:00:00)
  • Clear Liquid (12:00:00)
  • Unknown Device (09:00:00)

Case #8: Stonewalled

  • White Substance (03:00:00)
  • Yellow Fibers (15:00:00)
  • Bloody Powder (09:00:00)

Case #9: Shooting Star

  • White Liquid (12:00:00)
  • White Powder (09:00:00)
  • Gunpowder (09:00:00)

Case #10: The Bloom of Doom

  • Hair (03:00:00)
  • Goop (06:00:00)

Case #11: Hot Mess

  • Pink Crystals (03:00:00)
  • Cocktail Glasses (09:00:00)

Case #12: The Art of Murder

  • White Powder (03:00:00)
  • Cage Key (12:00:00)
  • Wrench (09:00:00)

Case #13: Gone Pear-Shaped

  • Fibers (09:00:00)

Case #14: Byte the Dust

  • Bloody Razor (03:00:00)
  • Ticket Strip (12:00:00)
  • Cremation Urn (12:00:00)
  • Gold Object (15:00:00)

Case #15: Murder on the Dance Floor

  • Yellow Goo (09:00:00)

Case #16: Buzz Kill

  • Bloody Brush (06:00:00)
  • Bottle of Kombucha (09:00:00)

Case #19: The Lost City

  • Hand Pump (15:00:00)

Case #20: No Mercy for Old Men

  • Purple Liquid (03:00:00)
  • Translucent Substance (09:00:00)

Case #21: Writer's Blocked

  • Bloody Ribbon (12:00:00)
  • Black Fibers (09:00:00)

Case #22: Color Me Murdered

  • Blood (03:00:00)
  • Blue Substance (12:00:00)
  • Translucent Substance (09:00:00)

Case #23: I Lost My Heart in Xerda

  • Chloroform-Soaked Cloth (06:00:00)
  • Human Heart (09:00:00)
  • Glowing Bug (09:00:00)


  • Rupert is one of the main characters to be flagged as a suspect in a case.
  • Rupert is one of the characters to appear as a quasi-suspect twice.

Case appearances



Promotional images


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