"This is my spot, Kate, this is where I stand."
—Captain Montgomery in Knockout
Roy Montgomery
Vital Statistics
Title Former Captain
Gender Male
Status Deceased
Cause of death Shot by Hal Lockwood
Spouse(s) Evelyn Montgomery (Wife)
Children Rebecca Montgomery (Daughter)
Mary Montgomery (Daughter)
Evan Montgomery (Son)
Character Information
Appearances Roy Montgomery - List of Appearances
Portrayed by Ruben Santiago-Hudson

NYPD Captain Roy Montgomery was Kate Beckett's boss at the Twelfth Precinct's Homicide Division. He carried a .38 Colt Detective Special as his sidearm, which he pointed at Dick Coonan during the latter's aborted escape attempt from the Twelfth Precinct. ("Sucker Punch") In the two other instances where he is seen with a gun, however, he used different revolvers; in "Murder Most Fowl", he carried a large-caliber revolver in a stainless finish, but in "Knockout", during his last stand against Hal Lockwood and his forces, he carried some kind of large revolver in a gunmetal finish and had a two-barreled Derringer pistol as a holdout weapon held in his left sleeve.



Sixteen years before Castle started, during the glory days of the Italian Mafia in New York City, Roy Montgomery was a rookie cop who looked up to John Raglan and Gary McCallister. He was dissatisfied with the way the Five Families openly flaunted their activities and presence in the public spotlight, and how they had bribed everyone in a position of authority and influence, to the point where he joined Raglan and McCallister in their kidnapping scheme, to make the Five Families pay a large amount of money to get back whoever they ended up kidnapping. ("Knockdown")

One night, in a blind alley near the back entrance to a Mafia hangout called "Sons of Palermo," they attempted to snatch a mobster named Joe Pulgatti. What they didn't anticipate was the presence of undercover FBI Special Agent Bob Armen, who went for Montgomery's gun. During the resulting struggle, the gun went off and killed Armen. In their attempt to cover up the murder, Raglan arrested Pulgatti for Armen's murder. ("Knockdown")

Some time later, an unnamed man somehow learned of the cover-up. But instead of turning them in, this man demanded the ransom money, and used it to acquire his current position of power and influence, which is one of enormous reach and scope, as he is referred to as "the Dragon", and appears to be at the root of attorney Johanna Beckett's murder. ("Knockout") At some point, Montgomery recorded a conversation with the man, then-Assistant DA William Bracken in which he confessed to blackmailing the three officers, planning Johanna's murder if she didn't stop investigating and having had many other people killed. Montgomery gave the tape to Johanna. She hid it in an elephant figurine she kept on her desk, but she never got to use it before her murder. ("Veritas")

While Raglan and McCallister tried to drown their guilt in alcohol, Montgomery threw all of his guilt into his job as a police officer of the NYPD, to the point where he would continue to feel guilty about never following up his suspicions in the death of Olivia Debiasse, even after Brady Thompson confessed to the crime, and notwithstanding the fact that there was evidence that implicated someone else. ("Kill the Messenger")

Beckett onwards

When Johanna's daughter Kate Beckett showed up at the Twelfth Precinct years later, Montgomery thought the Hand of God was pushing him to redeem himself, even though he knew that her mother had been murdered in order to keep the specifics of Bob Armen's murder from ever being made public knowledge. In their first meeting, Montgomery attempted to point her in the direction of the proof she was looking for, but failed.

When the death of bike messenger Caleb Shimansky started a chain of events that lead to the reopening of the investigation into Olivia Debiasse's murder, Montgomery was forced to confront his guilt over the fact that if he'd just dug a little deeper, then both Caleb Shimansky and false confessor Brady Thompson wouldn't have died, just to conceal the fact that Olivia was killed in order to hide her true parentage and prevent political scandal. What made him most satisfied at the end of the case was that he could finally provide Olivia's surviving family with answers. ("Kill the Messenger")

When Beckett learns that Jack Coonan was killed by the same man who had killed her mother, Montgomery is the first to ask her if she's all right and recommends that she step back from the case. ("Sucker Punch")

When Coonan was discovered to have not only killed his own brother Jack ("Sucker Punch"), but also Johanna Beckett, two of her associates in the Justice Initiative (a fictional version of the real-life Innocence Project) that were working on Joe Pulgatti's case ("Deep in Death"), and a courthouse document clerk, Montgomery is the first to notice something wrong with the way Coonan is leaving the Twelfth Precinct. ("Sucker Punch")

When investigating the murder of juror Joe McUsic, Montgomery realised that his friend, D.A. Lou Karnacki, had been involved in concealing evidence identifying Joe's murderer, demonstrating his commitment to justice by ordering Lou to turn himself in before he revealed the truth himself, despite Karnacki attempting to offer him the position of Police Commissioner if he should succeed in his re-election campaign ("Law & Murder")

When Hal Lockwood, the killer of both John Raglan and Gary McCallister, escapes police custody, he makes his way to Montgomery's house and threatens his family, revealing that he (Montgomery) had made an agreement with the unknown man to keep Beckett from investigating her mother's murder in return for keeping her, and his family, alive. Unable to choose either option, he decides to make a stand. He takes out certain case files (that he had kept all this time), and mails them to Michael Smith before luring Lockwood and his associates out of hiding, by pretending to bring Beckett to her doom in the hangar where Lockwood had stashed his escape helicopter. Instead, he had Castle drag her out of the hangar before making his last stand, successfully killing all four of Lockwood's associates before being shot twice by Lockwood himself. ("Knockout")

With his last breath, he tells Lockwood that the two of them are done, revealing that he had seen to the silence of the man who had ordered Johanna Beckett's death, just before killing Lockwood and then dying of his wounds. He left behind a wife and two girls. While the squad and Castle were aware of the truth of his death, they decided to keep it to themselves so he would not be dishonored. ("Knockout")


Over a year after his death, Montgomery retained a strong reputation with the team, with his successor, Captain Victoria Gates, noting that she acknowledged Montgomery's reputation with the detectives under his command and could only hope to inspire that level of loyalty herself some day. While she had some apparent suspicions about Montgomery's role in the events that led to his death even before the team revealed the full truth, she has never questioned the team for more information, suggesting that she acknowledges the good he did and sees no need to jeopardise that.

Montgomery's incriminating files allowed Michael Smith to establish the same deal Montgomery had with Bracken to protect Beckett. Eventually the files were destroyed, but Beckett was able to put together enough of them to identify Bracken. She then pretended there was another copy of the files and forced Bracken to back off.

The existence of Montgomery's recorded conversation of himself and his former training officers had with Bracken was later revealed to Kate by Michael Smith, recalling from a dream how he had tried to clue her in on this when she was looking for evidence during their first meeting, but she didn't get it at the time. In "Veritas", after Bracken frames her for murder after learning from her pursuit of Vulcan Simmons that she has nothing on him, Smith tells Kate of the tape and she finally understands what Montgomery had tried to tell her.

Castle supposes that Johanna hid it in a family possession. Having kept the elephant figurine on her own desk just like her mother had, Kate realizes Montgomery's tape must be inside and uses it to finally arrest Bracken. However, the tape was played in front of Internal Affairs to clear Kate's name and thus Montgomery's own past was exposed. It's unknown how this affects his reputation.



  • Roy married Evelyn in 1981. He has two daughters, Rebecca and Mary. One of his family pictures shows him with a daughter, his wife, and a little boy ("Always"). This boy's relationship with Montgomery is never clarified. Hal Lockwood tried to coerce Montgomery into arranging Beckett's death; such was his love for his family that threats against them nearly caused Montgomery to comply ("Knockout").

Kate Beckett

  • Roy first met Kate when she was a rookie. She was going through the police archives on her mother's case (illegally) when walked in on her. It is later implied that he was in the archives office as part of his work in covering up his own (indirect) involvement in the murder. Whatever the case, he decided to take her under his wing. Montgomery often supported Beckett's decisions even when she acted improperly or behind his back, and took on the role of a father figure to her, partly to atone for his own sins. He made a deal with Senator Bracken, keeping Beckett from making progress on the case in exchange for Bracken letting her live. When this failed, he died to protect her from Hal Lockwood ("Knockout"). After death, he still continued to protect her in a way as his files were used by Michael Smith to force Bracken to back off. Kate also protected his reputation by getting Castle, Ryan and Esposito to keep quiet about his actions. In "Veritas", Kate realized that in their first meeting, Montgomery had attempted to help her solve her mother's murder by suggesting she look for cassette tapes as he had given Johanna Beckett a recording that implicated Bracken in several crimes, including plotting Johanna's death. She is able to find Montgomery's tape and use it to finally bring Bracken down. However, in the process, she exposed his role in the death of Bob Armen to Internal Affairs and possibly ruined his reputation.

Richard Castle

  • Roy liked Castle, for many reasons. He claims this is to keep the Mayor happy, but he also respects Castle's abilities as an investigator, noting the writer's natural knack for the role to the point of speculating that his unknown father had a history in law enforcement. While his first loyalties were to his detectives, he considered Castle a friend. The two play poker regularly with the Mayor and Judge Markway. Montgomery later admits that he could have gotten rid of Castle at any time, but kept him on because he had such a good effect on Beckett; while she was a brilliant and driven investigator, her time with Castle was the first time she really had any fun at her job. When he needed a partner to help him save Beckett once, Montgomery turned to Castle, even over his other detectives.

Kevin Ryan and Javier Esposito

  • Montgomery was a father figure to the other two detectives of the 12th, but not to the extent that he was with Beckett. However, he was very protective of the two, going out of his way to protect Esposito when Internal Affairs was investigating him, for example. In return, the two kept his secret when he died to protect his reputation.

Michael Smith

  • It is unknown how Montgomery knew the mysterious lawyer Mr. Smith; however, the two were close friends. Smith even attended Roy's wedding in 1981. Smith didn't care about Beckett and wasn't willing to take on Senator Bracken, but such was the magnitude of the debt he owed his old friend that he was willing to blackmail Bracken to protect Beckett, even enduring torture to avoid spilling what he knew.

John Raglan and Gary McCallister

  • When Roy was a rookie, he was trained by John Raglan and Gary McCallister. He looked up to them, and considered them to be heroes. Eventually, he became entangled in their vigilante kidnapping scheme against the mafia. The two officers protected their rookie accomplice when Montgomery accidentally killed an undercover FBI agent during a botched kidnapping attempt. The three were later blackmailed out of their accumulated ransom money by then-Assistant DA Bracken, and covered up their crimes and his. Over the years, Montgomery erased all official records connecting him to the two older cops, and there is no evidence that he maintained his relationship with them after the kidnapping.


He appreciated Beckett's determination and diligence, but maintained a close watch on her in order to make sure any murder investigation went as smoothly as possible. He was amused by how much Richard Castle annoys Beckett, but also appreciates how effectively the two of them solve cases when they work together, to the point that he once speculated that Castle may have some family ties to the police through his unknown father to account for his natural skill in solving crimes. Whether, given later revelations about Castle's father, this indicates some specific knowledge on Montgomery's part is, as of the end of season 4, unclear.

He also demonstrated a strong attachment and respect for Beckett, commenting to Castle that he had never known anyone who can comfort the victims of violent crimes better than her ("Kill the Messenger"), to the point where he argued with the Governor and District Attorney of New York in order to accept a deal that would have allowed a newly discovered heroin trafficker, Dick Coonan, to walk free when he offered information that would have allowed them to capture the man who murdered Beckett's mother (although the deal became null and void when it turned out that the drug trafficker, Dick Coonan, was the killer and Coonan ended up being killed at Beckett's hands). His conduct in this case also implies that Montgomery was not aware of Coonan's role as a murderer in the Beckett case. ("Sucker Punch")

He carried a lot of guilt over his role in Bob Armen's death, which would lead to Johanna Beckett's death as a result. When Beckett walked into his life, he saw a chance for personal redemption in her and became something of a father figure to her. ("Knockout") Though it wasn't revealed until much later, in their first meeting Montgomery attempted to point her in the direction of evidence that would solve her mother's murder at the cost of revealing his own crimes. She didn't understand what he was trying to do at the time however. He had a particular loathing for dirty cops ("Kill the Messenger", "Den of Thieves", Knockdown"), mainly due to his own role in the death of Bob Armen, and the snowballing consequences. Unlike his training officers, however, Montgomery chose to seek redemption for his accidental crimes by becoming the best cop he could. This became something of a double-edged sword for him: on the one hand he refused to allow law enforcement officials to get away with dirty actions (like his friend Lou Karnacki), but he'd also beat himself up when he found out he'd made a mistake in the past (like with Olivia Debiasse's and Brady Thompson's case).

Whatever his flaws, Roy Montgomery showed and inspired great loyalty, was devoted to protecting people from criminals and rightly, as Beckett said, "died a hero". ("Knockout")



  • In his final episode Knockout, Montgomery mentions that he was protecting Kate "the way he should have protected her," referring to Beckett's mother. This seemed to indicate that Montgomery knew Kate's mother. This was later proven true in Veritas, which revealed he'd given Johanna proof that Bracken was corrupt.
  • Montgomery stated in Lucky Stiff, if he won the lottery, he would purchase, in his own words, "a big-ass boat, 60 footer, monster spinnaker hanging off the bow, two deep sea rods hanging off the stern."
  • In the 5th season premiere episode After the Storm, it was revealed Montgomery married in May of 1981.


Cast Nathan FillionStana KaticJon HuertasSeamus DeverTamala JonesRuben Santiago-HudsonMolly C. QuinnSusan SullivanPenny Johnson Jerald
Characters Richard CastleKate BeckettJavier EspositoKevin RyanLanie ParishRoy MontgomeryAlexis CastleMartha RodgersVictoria Gates
Seasons 1   •   2   •   3   •   4   •   5   •   6   •   7   •   8