65 pages • 2-hour read
Midnight Black
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Background
Content Warning: This section of the guide includes discussion of death.
Series Context: The Gray Man Saga
Midnight Black is the 14th novel in the Gray Man series, with the first installment, The Gray Man, published in 2009. Informed by author Mark Greaney’s academic background in international relations, the espionage saga focuses heavily on global politics, its landscape stretching from the US to Russia to Pakistan and beyond. The specific focus of the novel is covert espionage operations, often carried out by CIA members in tandem with non-official covers (NOCs) or deniable assets, agents whom a government can deny knowing if they are captured. Deniability allows governments to conduct sabotage missions in other countries, which would otherwise be seen as a breach of international law. Court, the eponymous Gray Man, is a former CIA agent who once worked as an NOC; however, after being betrayed by the agency, Court works as a freelance international assassin, only accepting jobs he deems morally righteous in the larger scheme of things.
The plot of Midnight Black continues from developments in which Court meets Zoya Zakharova (in Gunmetal Gray, published 2017), an SVR (Russian intelligence) agent who becomes a CIA asset. Zoya’s father was the head of the GRU, another Russian intelligence agency. Over the course of the next few novels, Zoya and Court’s relationship develops. In The Chaos Agent (2024), Zoya is captured in Cuba by an undercover Chinese spy and extradited to Russia in a spy swap—Zoya is wanted in Russia because she defected from the SVR.
Court immediately begins working on a plan to rescue Zoya as The Chaos Agent ends, meeting Hanely, his former handler, in Bogota, Columbia. In addition to Court, Zoya, and Hanley, Midnight Black brings back other well-known characters from the series, including Zack Hightower. Zack, a former CIA paramilitary and SEAL officer, is highly skilled in war operations. A close friend of Court’s, the older man headed Sierra Six, the elite team from which Court gets his code name “Six.” The term “gray man” itself refers to a spy who is an expert at blending into the background or going unnoticed.
Geopolitical Context: The Russo-Ukrainian War
Greaney is known for using ongoing political issues and crises to frame the action of his novels. The plot of Midnight Black revolves around the continuing repercussions of the Russo-Ukrainian War, widely regarded as the largest war in Europe since World War II. Though conflict between the two neighbors had been escalating since 2014, Russia’s 2022 invasion of Ukraine triggered full-scale war. As of 2025, the war has claimed over a million Russian and Ukrainian lives. Russian troops occupy almost 20% of Ukrainian territory, including Crimea (since 2014) and parts of the districts of Zaporizhzhia and Kherson (since 2022; “The Russia-Ukraine War Report Card, Feb 26, 2025.” Russia Matters).
Most major world powers and international organizations, such as the North Atlantic Treaty Organization (NATO), are critical of Russia’s onslaught against Ukraine. According to Amnesty International reports, Russia continues to commit human-rights violations in Ukraine, a view supported by the United Nations (“Ukraine 2024.” Amnesty International). Rights groups have also raised concerns about repressed civil liberties under President Vladimir Putin, and countries like the US, Canada, and the European Union have imposed economic sanctions against Russia. While Russia continues to wage war on the Ukrainian borders, Ukraine has retaliated with long-range missile and drone attacks on Russian military installations.
In Midnight Black, Greaney is sympathetic to the Ukrainian cause and presents contemporary Russia as a heavily surveilled, punitive state, a throwback to the between-world-wars era and the Cold War. For instance, Zoya is held in a penal colony based on a gulag, the Soviet-era forced labor camps where dissidents were incarcerated. Further, Russia is shown to be rife with internal division, polarized between pro-war nationalists and anti-war dissidents.
The novel also draws attention to the price that ordinary Russian citizens have paid for the war, with a character telling Court that many families in his buildings have lost a child on the front. The fictional observation is based on real-life reports: A feature from The Guardian notes, “[T]he war in Ukraine has proved far deadlier for the Kremlin than other recent conflicts: Russia’s losses are roughly 15 times greater than those suffered during the Soviet Union’s decade-long war in Afghanistan” (Sauer, Pjotr. “One Million and Counting: Russian Casualties Hit Milestone in Ukraine War.” The Guardian, 22 June 2025).
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