Midnight Black

Midnight Black (2025) by Mark Greaney is the 14th book in the Gray Man espionage thriller series, which features Court Gentry, an assassin known as the Gray Man. In this installment, Court embarks on a perilous mission to rescue his lover, Zoya Zakharova, who is imprisoned in a Russian gulag. Filled with high-stakes action, geopolitical intrigue, and a personal quest that tests Court’s limits, the narrative explores themes such as The Importance of Courage and Resilience to Survival, The Human Cost of War and Espionage, and The Power of Love and Loyalty. The Gray Man, a movie based on the series, was released in 2022, starring Ryan Gosling.

This guide refers to the 2025 Sphere, Little, Brown Book Group Kindle edition.

Content Warning: The source material and guide feature depictions of death, graphic violence, sexual violence and harassment, physical abuse, emotional abuse, and cursing.

Plot Summary

Courtland “Court” Gentry (code names “Gray Man,” “Six,” and “Violator”) is on his most personal, desperate mission yet. Six months ago, Court’s lover and former Russian intelligence officer Zoya Zakharova was traded by China to Russia in a spy swap. Zoya’s whereabouts are unknown, but there are whispers that she may have been executed. Refusing to believe that Zoya is dead, Court has just one objective: getting into Russia and liberating Zoya. Court, a former Central Intelligence Agency (CIA) officer turned assassin for hire, has little American support in his perilous quest as he performs hits and strikes in exchange for intel on getting into Russia.

As the novel opens, Court kills Italian mafia members in Bucharest, Romania, for a rival gang, hoping to learn the name of a ship that will take him to Russia. He also ends up killing the men who hired him after discovering that they planned to double-cross him. He is on his way to the port of Constanta when he gets a call from Matthew Hanley, the head of the CIA’s Colombia operations, to head to Riga, Lithuania, instead, where he can find a more reliable conduit to Russia through his old CIA associate, Dr. Milda Berzina.

Meanwhile, an urgent web of espionage is unfolding on the world stage, raising the stakes for Court. As the Russian war with Ukraine continues, Russia is focusing on pro-Ukraine targets across Europe through a secret unit of the GRU, its foreign military intelligence agency. The CIA hires Zack Hightower, a friend of Court and Hanley, to take down Karol Dvorak, the head of the GRU’s covert unit. For the operation, Zack will receive help from the New Russia Council (NRC), a Russian government in exile formed by the billionaire Mikhail Sorkin. At the same time, there is infighting between the intelligence agencies of Russia, with the Federal Security Service (FSB) and GRU at constant loggerheads, while anti-war rebels carry out hits across Russia.

Zoya is still alive and is incarcerated at Yavas, a penal colony in Mordovia, deep in the Russian woods. After she was traded by China, Zoya was taken to the Lefortovo prison in Moscow, where she was tortured for information, starved, and confined to a refrigerated cell. In Yavas, a labor camp, she spends her days stitching military uniforms.

Natan Yarovoy, a highly popular dissident Russian politician, and his wife, Nadia Yarovaya, are also being held at Yavas, in separate prisons. Their presence makes the Yavas penal colony a site of interest for both the NRC and a rebel organization, the Freedom of Russia Legion. When CIA surveillance from hacked prison systems in Russia identifies Zoya at Yavas, they put a plan into motion.

Hanley hatches an elaborate mission in which Zack, who was a SEAL officer before he went under non-official cover for the CIA, will help the NRC and the Ukrainians break Yarovoy out of prison with an aerial strike. Yarovoy is a powerful symbol of resistance against Russia because he defeated incumbent prime minister Peskov in a popular election before Peskov declared the election rigged and imprisoned Yarovoy.

In Riga, Milda provides Court with information on a ship to Russia and connects him to a contact in Moscow. Since her house is surveilled by the GRU, Court’s presence is detected. Court figures out that Milda is in trouble and drives with her to a forest with GRU members in pursuit. Zack meets them there and kills the GRU team. Court and Zack head to Finland; Court plans to take a cargo ship to a port near St. Petersburg, Russia.

Dvorak receives intel from an FSB officer named Eriks Leonidovich Baronov that the man who killed his team in Riga is now in Finland. Baronov gives Zack’s coordinates to Dvorak, and in the ensuing gunfight, Zack captures Dvorak. Dvorak reveals that the FSB has an insider on the NRC who leaked Zack’s location. The FSB mole is eliminated, and the NRC speeds up its operations, as it is now known that an American asset is working for them.

The plot threads converge as Court arrives in Russia and Zoya strikes up a friendship with Nadia Yarovaya. Court’s contact introduces him to the Legion fighters. They agree to help him break Zoya out of Yavas, as long as he also rescues Nadia. As Court and the Legion members drive to Yavas, Zack and the Ukrainians launch an aerial attack on Russia via drones and missiles.

Since the missiles are aimed initially at the city of Voronezh, Russian intelligence is confused into believing that Voronezh is the target and directs all nearby troops to the airbase. However, the missiles are only clearing the path for aircraft to head to Yavas.

Meanwhile, Baronov steps up security in Yavas because he believes that Court will be arriving there soon. Baronov’s uncanny knowledge of Court’s actions is explained in the novel’s biggest twist: He tells Zoya that he was one of her interrogating officers in Moscow and drugged her into a semiconscious state. Under the influence of sedatives and psychotropic drugs, Zoya told Baronov about Court and how he would stop at nothing to get to her.

Zoya is crushed by the realization that she inadvertently compromised Court. However, she does not allow herself to despair for long; she plans a prison escape so that she can tell Court that Yavas is a trap. Just as Zoya manages to break out of her cell, explosives are dropped on the prison. Zack and his team join them via helicopter, fast-roping to the roof to rescue Yarovoy. Court kills all the guards.

Court and Zoya reunite, the Yarovoy and Nadia are rescued, and Zack manages to fly everyone, including a captured Baronov, out of Yavas. As the novel ends, Hanley is ostensibly fired from the CIA for his off-the-grid support of the Ukrainian operation. However, the firing is a cover, with the CIA deputy director of operations asking Hanley to run a covert agency that deploys assets like Zack and Court. Court and Zoya barely get an hour together before Court leaves on an urgent operation with Hanley.