65 pages • 2-hour read
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Content Warning: This section of the guide includes discussion of death, graphic violence, physical abuse, emotional abuse, and cursing.
Courtland “Court” Gentry, a former Central Intelligence Agency (CIA) officer who now works as an assassin for hire, is on a personal assignment in the Ferentari neighborhood of Bucharest, Romania. Court has to kill five armed men from the Italian ‘Ndrangheta mafia, who are pretending to fit into their surroundings. Though Court has a phantom headache, a response to the trauma he has endured in his line of work, he cannot allow the pain to distract him. He must complete this assignment to rescue his lover, former SVR (Russian foreign intelligence) officer Zoya Zakharova, who disappeared in Russia months ago. Zoya is thought to have been executed, but Court refuses to believe the rumor.
Although the armed men outnumber him five to one, Court is undaunted. He gets up from his chair, prompting the men—scattered around the bar and watching Court—to converge on him. Court pulls out a subcompact pistol and swings around to face them.
Dorin Balan, the leader of the group who hired Court, is on the roof of a multistoried parking garage near the bar, awaiting news from Court. It was supposed to have been carried out at midnight, but Balan and his men have only heard a single gunshot. Balan is the Nasul, or godfather, of a Romanian mafia called the Balan Brigazi. Finishing off the ‘Ndrangheta is important for Balan since they’ve been taking away his business.
Before Russia declared war on Ukraine, Balan’s chief income came from sex-trafficking Russian and Eastern European women to the rest of the world. Though business dwindled after the war, Balan pivoted and began smuggling luxury goods into Russia (which is facing import sanctions because of the war) at a high mark-up. The new business made Balan millions of dollars until the Italian ‘Ndrangheta emerged as competition, smuggling expensive perfumes, wines, and cheeses into Russia.
Balan had been debating how to get rid of his Italian rivals when he received a call from an unknown American assassin (Court), offering to do any job for Balan in exchange for passage to Russia. Balan agreed, but he did not tell the American that he had another job for him—killing a capo, or Italian mafia leader—before sending him to Russia.
Meanwhile, Balan’s nephew Christofer brings news of Court’s hit: He killed all five Italian gang members before they had time to react. He used a silencer, explaining why most of the gunshots couldn’t be heard. Court was supposed to come to the rooftop with Christofer, but instead, he left the bar.
As the men talk, Court arrives at the rooftop. He asks Balan to hold up his end of their deal and put Court into a Turkish ship leaving for Russia tomorrow. Balan replies that Court needs to do another job for him, after which he can leave on another ship, departing from Constanta four days later. Court refuses, telling Balan that he does not have time to lose.
Court engages Balan in a conversation so that he can take stock of his surroundings and Balan’s men. He had expected to be double-crossed since he is dealing with the Brigazi, and he prepared accordingly. When Court left the bar, instead of going to the parking garage with Christofer, he got two satchels of Semtex (an explosive) from a weapons truck he stole a couple of days ago, and he has placed one satchel in a parked car on the roof.
As Court promises to carry on Balan’s additional task after he returns from Russia, Balan tells him that there’s no “after”; Court is bound to be killed in Russia. Court must agree to kill the capo or prepare to die.
Court tells Balan that killing him will be tough, as they are in Court’s territory. He lifts his hand to show the Brigazi men the tiny remote he holds and tells them that it’s linked to explosives hidden in a car on the roof. If Balan doesn’t let him leave, Court will detonate the Semtex.
Balan thinks that Court is bluffing and orders his men to search the rooftop for the Semtex. As the men spot something in a parked car, Court backs toward the garage’s gate and pushes the button. An explosion rings out, and Court scrambles down the stairwell, aware that the blast could not have killed too many men since he himself is unharmed.
However, Court retraces his steps when he realizes that he does not have the name of the ship from Turkey. Hoping that Balan is still alive, he runs up the stairs.
As Court gets to the doorway, he hears racing footsteps. He emerges onto the rooftop, shooting blindly and taking down the men closest to him. He continues to shoot indiscriminately until he has killed everyone except Balan. The badly injured Balan is propped up against a car. Begging Court for mercy, Balan tells him that the ship is the Mygan and that it calls at Constanta the next day at four o’clock in the afternoon. If Court lets him live, Balan will put in a call to Istanbul ensuring that Court gets on the ship. Court tells Balan that he can handle matters from there and shoots him.
Court makes his way down to a lower floor of the parking lot, where he has stowed the second satchel of Semtex in an old Mercedes. He gets into the Mercedes and drives as more cars emerge on his level, possibly carrying Balan Brigazi members, out for revenge. Court reverses his car at high speed as the other vehicles speed toward him, intending to crash out of the lot into the air. Just before the Mercedes breaks through the cables at the end of the lot, Court throws the satchel out the window and leans back in his seat.
The Romanians watch the Mercedes fly out and crash to the ground, its grill facing upward. They assume that Court is still trapped in the car and aim their guns at it. Just then, Court clicks the remote and detonates the satchel, still in the parking garage. It explodes, and Court waits for the debris to stop falling and scrambles out of the car. Though he is injured, he is still alive. The only thought in his mind is to get to the Mygan and, from there, to Zoya.
The narrative flashes back to a month earlier than the present timeline. Zack Hightower (Court’s friend and a recurring character in the Gray Man series) is under house arrest in a mansion in Charlottesville, Virginia, for going rogue on a previous operation. Zack is being guarded by nine CIA staffers. Though the staffers are supposed to keep Zack at an arm’s length, they have struck up a friendship with the charismatic older man, a former SEAL who has worked with Court in many operations.
CIA executive Angela Lacy arrives at the mansion with a fresh assignment for Zack. Zack has to kill a GRU (Russian foreign intelligence) lieutenant colonel, Karol Dvorak, who is harming Western interests in Eastern Europe and Russia. In the assignment, Zack will be working for Russian iron baron Mikhail Sorkin.
Sorkin started a political movement called the New Russia Council (NRC) that positions itself as an alternative to the Russian government and trains Russian dissidents. Sorkin is aligned with American interests in checking Russia’s power. Zack accepts the assignment and asks Lacy if she has heard from the freelancer known as the “Violator” or “Six” (Court’s aliases).
Lacy tells Zack that Court has gone dark since the news of Zoya’s execution. She promises to find more intel on Court, whom she has worked with and likes. Meanwhile, Zack must leave for Czechia, where Karol Dvorak is located, straightaway.
In the present timeline, CIA Deputy Chief of Station Matthew Hanley is at his new office in Bogota, Colombia, worrying about his friends and employees, Court and Zoya. Hanley thinks it is likely that Zoya is dead—intel says that a female former SVR officer was recently executed in Moscow’s Lefortovo Prison, the same jail where Zoya was taken.
Hanley gets a call from the embassy in Bulgaria about the hit on the mafia in Bucharest. As his contact describes the massacre, Hanley understands that the killing was carried out in Court’s characteristic style. Since Court seems to be acting recklessly, Hanley fears for his future and calls Court on an encrypted line.
Court is at the port of Constanta and wondering how to enter the Mygan—a heavily surveilled oil tanker—undetected when he gets Hanley’s call. When Hanley asks Court what he plans to do once he gets into Russia, Court tells Hanley that he will kidnap a senior Russian politician and hold them hostage in exchange for information about Zoya. Hanley says that he has a better lead for Court: a former CIA contact who lives in Riga, Latvia. Instead of taking the Mygan, Court must meet the older woman before he heads to Russia. Court agrees.
Zoya is alive and housed in the Women’s Correctional Colony IK-2 Yavas in Mordovia, Russia. Mordovia is home to 15 prisons, making it a penal colony of labor camps. Natan Yarovoy, the most high-profile critic of Russian president Vitaly Peskov, is being held at one of the all-male prisons. Yarovoy defeated Peskov in the last election, but the election was declared invalid, and Yarovoy was imprisoned. His wife, Nadia Yarovaya, is incarcerated in nearby Yavas, like Zoya, but the husband and wife are not allowed to see each other.
Zoya is at work in a Yavas sewing shop, where prisoners sew military garments in 12-hour shifts, overseen by guards. Zoya has already stitched 220 pairs of trousers that day when a guard appears at her workstation to summon her outside.
Two male guards escort Zoya down the building’s basement. Fearing that she is about to be tortured for information, Zoya begins to disassociate from herself. However, she is pushed into a meeting room, where an unknown Russian official waits for her. When Zoya introduces herself by her prison serial number, the man makes it clear that he knows Zoya’s true identity, telling her that, though she doesn’t remember it, they have met before.
Introducing himself as Major Colonel Eriks Leonidovich Baronov, the man shows Zoya his comprehensive file on her. Baronov tells Zoya that her case caught his attention because his specialty is hunting for internal enemies. The fact that Zoya is alive, despite being under an Odessa order (capture or kill) from the Kremlin, indicates that she has a secret benefactor within the Russian administration. Inna Sorokina, a former SVR defector under the same order, was executed recently.
Zoya assures Baronov that she doesn’t have a patron within the Russian services. He may think that she’s been treated favorably in prison, but she has been starved and locked in a refrigerated cell. Baronov refuses to believe Zoya. He promises her that he will soon crack her network and have her executed. Zoya calmly tells Baronov that the impending execution means that soon she will be resting, like Inna.
After Zoya is led out, Baronov asks the guards about her. The guards tell Baronov that Zoya is extremely reserved, even keeping her eyes shut when she is led from her living facilities to the labor stations. Baronov reprimands the guards for underestimating Zoya: She keeps her eyes closed so that she can memorize the prison’s layout in case she has an opportunity to break out in the dark. He urges the guards to keep a close watch on Zoya.
Meanwhile, back in her bunk, Zoya wonders why the intelligence agencies are bothering with her after months of incarceration. As she dreams once again of escape, she is wracked by the persistent cough that has plagued her since she was imprisoned.
Denis Maskaev, a retired Russian special-ops commander and military hero, is on the day’s last commuter train from Moscow to Obninsk. As the train reaches Obninsk, Denis watches certain disembarking passengers; like him, they are members of a Russian resistance movement called the Freedom of Russia Legion. Though ex-military, Denis opposes President Vitaly Peskov’s regime and conducts raids against government machinery and infrastructure. Denis was badly injured in the last operation he carried out for the Russian military. Though he has largely healed, he is left with a persistent, excruciating headache, the result of both physical and emotional trauma.
Today’s plan is to rob an incoming freight train packed with military gear. Denis’s team of 11 people, including their cell leader, Leonid, disembarks at the station in pairs, refusing to look at each other. They gather in the woods bordering the far end of the station. While five people keep watch, Denis, Leonid, and the others head back to the station.
However, a team of police officers arrives at the station around the same time, scanning the tracks. Before Denis and the others can duck, the officers open fire, killing Leonid instantly. Denis detonates an explosive device that they’d attached to a track earlier. The explosion kills four police officers and topples the military-cargo car, creating cover for the rebels, who run back to the forest. Just as they’re about to reach the line of trees, the police shoot again, killing Denis’s colleague Kostya. Another colleague, Tatyana, has her palm slashed in the attack.
The survivors manage to escape in a minivan driven by 19-year-old Vera, the youngest team member. As they mourn their losses, the group decides that Denis must be their next leader. Denis reluctantly accepts. He thinks that their next assignment should be to assassinate a high-profile Russian leader.
Dr. Milda Berzina is the Latvian contact to whom Hanley directed Court. Seventy-six-year-old Milda is an expert on the politics of Eastern Europe and Russia, and she hosts a well-known podcast called Flash Focus on the Baltic. Widowed, Milda lives by herself in an apartment in the beautiful old quarters of Riga. Court watches Milda’s apartment and learns that she is being surveilled, perhaps by one of Russia’s intelligence agencies.
Court shares the information with Hanley. Hanley is surprised that Milda is being surveilled since she is no longer an active CIA contact. Milda helped political dissidents out of Russia during the Cold War but has been quiet since. From Court’s description of the agents watching Milda, Hanley can tell that they’re non-Russian nationals, possibly working for Russia’s GRU, which Karol Dvorak heads. Hanley asks Court to approach Milda carefully and hangs up. He calls someone else (later revealed to be Zack) to update him about the new situation.
Baronov has been following Court’s movements; because of Court’s assassinations across the Baltics and in Bucharest, he has caught the Russian agencies’ attention. The Russians have given him a code name, “Chayka,” after the site of his first attack. It is clear to them that Chayka wants to get into Russia at all costs. Baronov does not want to block Chayka because he wants the American on his turf.
In Riga, Milda is woken up in the middle of the night by the sound of running water in her bathroom. She sees a note on her bedside table telling her to come to her bathroom because her apartment is being audio-surveilled. Mila finds Court, whom she has never met, in the bathroom. Court tells Mila not to be scared of him because he has been sent by her old contacts in the CIA. He’s turned on the shower so that their voices don’t get picked up by surveillance.
As Court explains that he needs to get into Russia, Mila offers to make him tea. Court tells her that making tea in the middle of the night would be a bad idea because any unusual activity would be picked up by surveillance. Milda reminds Court that running a shower at one o’clock in the morning is also an unusual activity. Court realizes that he’s made a mistake.
This fast-paced novel is told from a limited third-person point of view that shifts between multiple characters, such as Court, Zoya, Hanley, and Baronov. The choice of point of view helps immediately immerse readers in parallel storylines spread over a vast geography, from Zack’s safehouse in Charlottesville to Zoya’s prison in Yavas. Following a largely linear chronology, the novel uses devices such as flashbacks and circle-backs to provide backstory and add urgency to the plot, as in the case of Zack’s chapter, which unfolds a month prior to the main timeline. The prior timeline tells readers that the gears of the plot are already moving, with various actors and factions in play before Court even gets into Russia.
A sense of urgency permeates the plot from the beginning, with Court racing against time to get to Zoya, an urgency heightened by the possibility of Zoya’s execution. To emphasize the importance of conserving time, the plot is filled with time stamps, such as Court making sure that he carries out the Bucharest hit at midnight. Contrary to the propulsive role that time plays in Court’s sections, in Zoya’s section, time is reduced to being regimented and repetitive, mirroring her sense of despair and confinement. An example of this different manifestation of time in the narrative can be seen in the description of Zoya’s workday, wherein she notes that “other than fifteen minutes for lunch, plus two strictly enforced five-minute bathroom breaks, and an hour in the afternoon doing mandatory calisthenics in the prison yard, the woman at station 46 ha[ve] not stopped working all day” (66). The juxtaposition of the strict, portioned-out breaks with the endlessness of the workday evokes the hopelessness that Zoya experiences in the penal colony. The penal colony itself becomes an important symbol of oppression and despair in the novel.
These opening chapters highlight author Mark Greaney’s use of detail and nomenclature in lending authenticity to his universe. For instance, during the Freedom of Russia Legion’s attack on the train, Greaney names not just the guns that the Legion members carry but also the size of the bullets: “As the car doors opened, both Denis and Kostya shouldered their Vityazes and opened fire on the windshields, tearing through the glass with dozens of 9-millimeter rounds” (93). The use of detail evokes the meticulous, precise work that goes into planning covert operations and espionage, as in the case of the attack on the train, hewing closely to the conventions of espionage fiction.
Graphic violence is ubiquitous in these chapters, illustrating the text’s themes of The Human Cost of War and Espionage. For instance, during Denis’s operation, his cell leader, Leonid, is killed by a bullet, the “top of the […] skull […] gone, and brain ooze[s] through his blond hair” (92). Denis does not have the time to mourn Leonid; instead, he grabs the remote from the dead man’s hand and activates the explosives in the train car. The juxtaposition of violence with cold efficiency showcases how extreme situations do not even allow participants to experience grief or sorrow, adding tension to their depiction as caring, three-dimensional characters.
Since this is a fast-paced espionage thriller, the plot skews toward action rather than the interior lives of the characters, using gesture, nuance, and carefully selected dialogue to flesh out characters. Court’s mantra that insists that Zoya is “not dead” is an example of such a nuance, illustrating his desperation and determination in a few words. Another is Hanley’s use of “kid” to refer to Court, showcasing the warm, paternal feelings that the older man has for his protégé. Though characters in the novel are involved in a high-body-count game of espionage, their interpersonal relationships run deep, illustrating the theme of The Power of Love and Loyalty.
These early chapters also provide vital backstory to Midnight Black, revealing that Zoya was traded by China to Moscow in exchange for a spy they wanted and that Court and Hanley spent several months trying to track Zoya before Court decided to go freelance to save her. Additionally, they showcase Greaney’s characteristic use of humor and sharp dialogue to enliven his plot. For example, in Court’s exchanges with Balan, he tells the man that after having “successfully completed stage ‘fuck around,’ […] [he] now [is] entering stage ‘find out’” (28). Greaney balances this dry humor with graphic violence and action to exacerbate the plot’s tension.



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