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Till death do us part.
~ Ray and Syd
Sydney: I love you, Ray.
Ray: Love you too, Syd.
~ Ray and Syd

Ray Donovan and Sydney Manning are major antagonists in the crime-drama TV series Criminal Minds. They are a husband-and-wife killing duo that appear as the main antagonists of the Season 6 episode "The Thirteenth Step".

Ray was portrayed by Jonathan Tucker (who also portrayed Matthew Brown in Hannibal and Hodak in Charlie's Angels), while Sydney was portrayed by Adrianne Palicki, who portrayed Ms. Perkins in John Wick.

Biography

Ray Donovan was born in Devil's Lake, North Dakota, while Sydney Manning was born in Spokane, Washington. In childhood, both suffered sexual abuse at the hands of their fathers. As a result, both were put into foster homes. As teenagers, they began abusing drugs and alcohol to help them cope with the trauma, which would ultimately end up getting them in trouble with the law. Some time after, Raymond and Sydney met in Alcoholics Anonymous, where they were able to relate with one another. Ray was still not over his ex-girlfriend, Amy Wichowsky, so Sydney decided to poison her and make it look like she overdosed. Raymond began to date Sydney, but they had trouble with completing the last steps of the program, and this trouble and relapse would lead them to committing a spree of crimes.

The Thirteenth Step

In 2011, the duo, young and in love, stop at a gas station in Miles City, Montana. While inside, they start contemplating marriage, which a customer overhears, and tells them that marriage is a mistake. Offended at the man's remarks, Ray pulls out a gun and shoots him. Joining in with her lover, Sydney pulls out her gun and begins shooting various people. The duo claimed six victims in Miles City and then went on to claim more in Billings, Montana, afterwards blowing the gas station up.

In Helena, Montana, Ray stops at an Alcohol Support meeting where he tells his story to a group and tells them he's having trouble with the eighth and ninth step. While Ray is in the meeting, Sydney seduces and robs a man named Jason, pistol whipping him after they have sex. When Ray is told by the group leader Tim, that he needs to accept his shortcomings and make amends, Ray takes this to mean that Tim is blaming him for being molested. Offended, Ray begins shooting Tim, to which Sydney comes in and starts shooting as well. After the massacre, Ray and Syd flee in Jason's convertible.

While driving through Missoula, Sydney suggests that she and Ray should stop the senseless killing and go take revenge on their fathers. Agreeing with Syd, Ray drives to his old house and confronts his father, holding him at gunpoint. He torments his father by playing Russian roulette, but Sydney grows impatient and ends up shooting the father. After a brief fight and make-up session, the duo head to Spokane, Washington, to take revenge on Syd's father. Sydney confronts her father at his gas station and holds him at gunpoint.

Her father apologizes to her and claims that he's found God, but neither Syd nor Ray believe that what he did can be forgiven. Both Syd and Ray relentlessly beat the father, but his daughter walks in. Sydney, believing that her father was molesting the girl, too, tries comforting her, while Ray takes the father to the back room and kills him.

The duo attempt to leave the gas station, but the BAU pull in, and get into a gun fight. Agent Derek Morgan ends up wounding Sydney, so they flee back into the station. While acting as a hostage negotiator, Morgan tells Raymond that Sydney murdered Amy, which finally pushes Raymond over the edge. He tearfully strangles Sydney to death, and then gets in his car and drives at full speed toward the BAU, forcing them to shoot him dead.

Victims

Ray

  • 1: Unnamed Miles City man - Shot multiple times.
  • 2: Unnamed Billings man - Shot with shotgun.
  • 3: Unnamed Billings man - Shot three times with shotgun.
  • 4: Unnamed Billings school teacher - Shot with shotgun.
  • 5: Unnamed Billings man - Beaten with crowbar.
  • 6: Tim - Shot multiple times.
  • 7: Unnamed Alcohol Support group member - Shot in the back.
  • 8: Jason - Shot in the head.
  • 9: Gary Manning - Beaten and shot.
  • 10: Sydney Manning - Strangled.

Sydney

  • 1: Amy Wichowsky - Poisoned with alcohol and heroin.
  • 2: Unnamed Miles City man - Shot multiple times.
  • 3: Unnamed Miles City man - Shot three times.
  • 4: Unnamed Billings store clerk - Shot four times and sodomized with a tire iron.
  • 5: Unnamed Billings man - Beaten with a bat.
  • 6: Unnamed Billings adolescent - Shot with shotgun.
  • 7: Unnamed Billings man - Blown up in the explosion.
  • 8: Paul Donovan - Shot in the head.

Not Specified

  • N. Apu - Beaten, killed off-screen prior.
  • Bowman Store Clerk - Beaten, killed off-screen prior.
  • Unnamed Miles City woman - Killed off-screen.
  • Unnamed Miles City woman - Killed off-screen.
  • Unnamed Miles City man - Killed off-screen.
  • 7 nameless Alcohol Support group members - Killed off-screen, bodies seen.

Gallery

Trivia

Navigation

           Criminal Minds Logo.png'Mary MeadowsCategory:Criminal Minds Villains

Season 1
Adrian Bale | Bruno Hawks | Clara Hayes | Cory Bridges | David Walker | Donald Curtis | Eddie Mays | Edward Hill | Hassan Nadir | Jackson Cally & His Tribe | Jacob Dawes | L.D.S.K. | Maggie Lowe | Mark Gregory | Mary Mays | Pablo Vargas | Richard Slessman | Ted Bryar | The Fisher King | The Footpath Killer | The Fox | The Keystone Killer | The Seattle Strangler | The Tommy Killer | The Vigilante | Vincent Perotta | Vincent Shyer | Will Sykes


Season 2
Amber Canardo | Carl Buford | Charles Holcombe | Frank Breitkopf | Jamal Abaza | Jeffrey Charles | Kenneth Roberts | Lyov Lysowksy | Marcus Younger | Michael Earlson | Paul and Johnny Mulford | Ronald Weems | Roy Woodridge | Sarah Danlin | Terrance Wakeland | The Fisher King | The Hollow Man | The Mill Creek Killer | The Stripping Bandit | Tobias Hankel | Tony Canardo | Vincent Stiles | William Lee


Season 3
23rd Street Killers | Anna Begley | Brian Matloff | Charlie Wilkinson | Chester Hardwick | Francis Goehring | Gary and Ervin Robles | Glen Hill | Henry Frost | Jason Clark Battle | Jeremy Andrus | Joe Smith | Lucky | Mike Hicks | Owen Savage | Peter Redding | Richard Jacobs | Ryan Phillips | Stanley Howard | Steven Fitzgerald | Susan Jacobs | The Campus Killer | The Have-You-Seen-Me Murderer | True Night


Season 4
Adam Jackson | Animal | Armando Ruis Salinas | Ben Abner | Benjamin Cyrus | Chad Brown | Chloe Kelcher | Claire Bates | Danny Murphy | Eric Ryan Olson | Floyd Hansen | Gary Michaels | Henry Grace | Hugh Rollins | Ian Coakley | Leo Kane | Lucas Turner | Mason Turner | Megan Kane | New York Terrorist Cell | Paul Silvano | Robert Parker | Roderick Gless | Romani Family | Sam | Separatarian Sect | Steven Baleman | The Angel Maker | The Reaper | The Road Warrior | Tommy Wheeler | Vincent Rowlings | William Harris


Season 5
Anita Roycewood | Arthur Malcolm | Bill Hodges | Boyd Schuller | Connor O'Brien | Dale Schrader | Darrin Call | Earl Bulford | Gina King | Joe Belser | John Vincent Bell | Miranda Dracar | Owen Porter | Patrick Meyers | Prince of Darkness | Ray Campion | Robert Burke | Robert Johnson | Ronald Boyd | Samantha Malcolm | The Fox | The Hollow Creek Killer | The Reaper | The Reimanns | Tony Mecacci | Turner's Group | Wade Hatchett | William O'Brien | Will Summers


Season 6
Ben Foster | Bill Thomas | Blake Wells | Brandon Stiles | Drew Jacobs | Greg Phinney | Hollis Walker Jr. | Ian Doyle | James Barrett | James Stanworth | James Thomas | Jane Gould | Jeremy Sayer | Kaman Scott | Lucy (Criminal Minds) | Michael Kosina | Prince of Darkness | Ray Donovan | Rhett Walden | Robert Bremmer | Shane Wyland | Shelley Chamberlain | Steve | Sydney Manning | The Butcher


Season 7
Bill Rogers | Caleb Rossmore | Chase Whitaker | Chloe Donaghy | Chris Shelton | Clark Preston | Colonel Ron Massey | Curtis Banks | Ben Bradstone | Donald and Linda Collins | Dylan Kohler | George Kelling | Harvey Morell | Herman Scobie | Ian Doyle | Izzy Rogers | James Heathridge | J.B. Allen | Jeffrey Collins | Jimmy Hall | Lachlan McDermott | Lieutenant Tawes | Luke Dolan | Malcolm Ford | Margaret Hallman | Matthew Downs | Mike Janeczko | Randy Slade | Robert Adams | Rodney Garrett | The Face Cards | The Piano Man | The Womb Raider | Travis James | Trevor Mills


Season 8
Adam Rain | Arthur Rykov | Bryan Hughes | Carl Buford | Carl Finster | Chad Mills | David Roy Turner | Diane Turner | Donnie Bidwell | Ellen Russell | Emma Kerrigan | Jason Nelson | John Nelson | Jonathan Ray Covey | Larry Feretich | Mark Jackson | Matt and Josh Moore | Paul Westin | Peter Harper | Phillip Connor | Raoul Whalen | Rodney Harris | Sera Morrison | Tess Mynock | The Replicator | The Silencer | Toby Whitewood | Tory Chapman | Willie Kestler


Season 9
Alan and Judith Anderson | Anton Harris | Carla Hines | Charles Johnson | Clifford Walsh | Colin Bramwell Daniel Milworth | Daria Samsen | David Wade Cunningham | Eddie Lee Wilcox | Eric Carcani | Ian Little | Jesse Gentry | Joe Bachner | John Nichols | Justin Mills | Leland Duncan | Mecklinburg Rapists | Nicole Jones | Owen McGregor | Owen McGregor's Partners | Ronald Underwood | Sheila Harrison | Sue Walsh | Tanner Johnson | The Doctor | Wallace Hines | Wayne Gulino | William Harding | Woodsman Killer


Season 10
Alex Zorgen | Allen Archer | Andrew Ford | Benton Farland | Brian Stiller | Chad Griffith | Claire Dunbar | Colin Dupley | Dale Shavers | Danny Stokes | Dinah Troy | Don Black | Donna Mangold | Donnie Mallick | Ellen Connell | Frank Cosgrove | Hayman Vasher | Jack Westbrook | James Burke | Jerry Tidwell | John David Bidwell | Jon Kanak | Justin Leu | Kyle Zorgen | Leo Jenkins | Marc Clifford | Miles Hendrick | Mr. Scratch | Patrick Butler | Patrick Jon Murphy | Peter Folkmore | Randall Jefferson Jones | Steven Parkett | The Mirror Man | Weeks


Season 11
Al Eisenmund | Andrew Meeks | Antonia Slade | Betty Wilson | Brian Cochran | Chazz Montolo | Claude Barlow | Dana Seavers | Eric Rawdon | Flora Martin | Giuseppe Montolo | Jacob DuFour | John Bradley | Johnson | Joseph Berzon | Lester Turner | Matthew Franks | Michael Thompson | Michael Peterson | Cat Adams | Mitchell Crossford | Mr. Scratch | Patrick Sorenson | Randy Jacobs | Robert Boles | Sam Burnett | Skull Tattoo Man | The Beantown Beheader | The Bomber | The Chemist | The Sniper | Tommy Larson | William Cochran | William Duke Mason | William Taylor


Season 12
Alan Crawford | Ben Davis | Bryce Jarvis | Cormac Burton | John David Bates | John Malone | Jonathan Rhodes | Kevin Decker | Kyle Ecklund | Lindsey Vaughn | Lionel Wilkins | Mark Tolson | Miss .45 | Mr. Scratch | Sara McLean | Stuart Barker | The Bone Crusher | The Crimson King | The Day/Night Killer | The Henson Twins | The Womb Raider | Zeke's Gang


Season 13
Asclepius | Caleb Sands | Cheryl Kaline | Desi Gutierrez | Gabriel Merza | Irene Jacobs | Jake Logan | Jess Carney | Josh Martin | Josh's Partners | Justin Franco | Kevin Peck | Kevon Winters | Lawrence Coleman | Lucky | Marcus Manning | Mark Henshaw | Mary Meadows | Melissa Miller | Michelle Gorman | Mr. Scratch | Mr. X | Sal Capilano | The Believers | The Central Park Ripper | The Messiah | The Neon Terror | Tony Capilano | William Lynch


Season 14
Arthur Brodie | Casey Allen Pinkner | Douglas Knight | Dustin Eisworth | Edward Addison | Elgin Family | Emmanuel Rask | Grace Lynch | Jacob Wallace | James and Marcus Wells | Jeremy Grant | Jordan Halloran | Mary Meadows | Roberta Lynch | Stephanie Carter | The Believers | The Chameleon | The Messiah | The Tall Man | Varnville Unsub | Wayne Hollis


Season 15
Beaumont Unsub | George Kyle Peters | Grace Lynch | Hayes Cullinan | Juliette Weaver | Louie's Gang | Louis Chaycon | Miss .45 | Sebastian Hurst | Shelby Mattson | The Chameleon


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