The Man in the High Castle Wikia
The Man in the High Castle Wikia

Hauptsturmführer Connolly was an American SS officer serving under Obergruppenführer John Smith, but was secretly an agent for Reinhard Heydrich.

Biography[]

Early Life[]

Born in the United States sometime before World War II, Connolly likely came of age during the Nazi occupation of the country. An early supporter of Nazism, he joined the Schutzstaffel (SS) and, by 1962, had attained the rank of Hauptsturmführer. Stationed in New York City, he served directly under Obergruppenführer John Smith.

Ambitious and calculating, Connolly’s aspirations drew the attention of Reinhard Heydrich, who ordered him to eliminate Smith—a staunch Hitler loyalist and potential obstacle to the Heusmann faction. Connolly secretly collaborated with a New York City Resistance cell, leaking Smith’s travel route in an effort to facilitate an assassination. However, his confidence wavered as he grew increasingly fearful of Heydrich’s notorious ruthlessness and the dire consequences of failure.

Season One[]

The assassination attempt ultimately failed, leaving a single resistance member alive and in custody. Connolly was present during the prisoner’s initial interrogation, where he witnessed Smith chastising the interrogator for insufficient brutality and demanding sustained beatings until the captive broke. Despite enduring several days of torture, the prisoner eventually revealed Connolly’s involvement.

Smith, uncertain of the confession’s credibility, decided to test Connolly. He confronted him with an unloaded gun, simulating a life-threatening scenario to gauge his reaction. Despite evident distress, Connolly steadfastly denied any wrongdoing, ultimately convincing Smith of his supposed innocence. Seizing the opportunity to prove his loyalty, Connolly personally beat the prisoner—covertly slipping him a silver spoon to facilitate suicide. Shortly after, Smith tasked Connolly with reviewing phone logs to identify a potential security breach.

Days later, Connolly reported the results of his investigation, asserting that no evidence of a breach had been found. Though reprimanded by Smith for his failure, Connolly offered information about the prisoner’s family connections, prompting Smith to escalate the interrogation. Together, they discovered the prisoner’s corpse, sparking suspicion about how he had obtained the spoon. Acting on Smith’s orders, Connolly detained the prison guard responsible, pending further investigation.

Tensions rose when Heydrich arrived in New York, ostensibly to retrieve Wegner but secretly to evaluate Smith’s loyalty. Connolly, attempting to ingratiate himself with the SS general, provided Heydrich with tea—a small but revealing act that Smith later uncovered. This discovery, combined with Connolly’s access to both Smith’s and Lautz’s travel records, confirmed his betrayal.

Smith summoned Connolly to the rooftop of the SS headquarters for a private confrontation. He questioned Connolly about failing to inform him of Heydrich’s arrival and noted his access to sensitive travel information. Though Connolly vehemently denied any wrongdoing, Smith feigned reassurance, suggesting Connolly had simply misunderstood Heydrich’s assassination plan. When Connolly admitted ignorance, Smith pushed him off the rooftop. His screams echoed as he fell to his death, staged as a suicide.

Connolly’s death served to mislead Heydrich, who overconfidently believed Smith was unaware of his schemes. Upon returning to his office, Smith instructed his interim aide, Major Klemm, to notify the authorities of Connolly’s “suicide.”

Appearance & Personality[]

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Relationships[]

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Appearances[]

Season One
"The New World"
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"Sunrise"
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"The Illustrated Woman"
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"Revelations"
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"The New Normal"
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"Three Monkeys"
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"Truth"
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"End of the World"
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"Kindness"
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"A Way Out"
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Gallery[]

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Notes & Trivia[]

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References[]