How to Become a Criminal Mastermind

Raymond Reddington is a fictional character and the central figure in the American television series The Blacklist, which aired on NBC from 2013 to 2023. Portrayed by James Spader, Reddington is a former US Naval Intelligence officer who became a high-profile criminal and later an FBI confidential informant. Once listed as number four on the FBI's Ten Most Wanted Fugitives, he voluntarily surrenders to Assistant Director Harold Cooper at the J. Edgar Hoover Building in Washington, D.C. Following his arrest and transfer to an FBI black site, Reddington offers to assist in capturing individuals he describes as particularly dangerous criminals and terrorists, many of whom are unknown to law enforcement. His cooperation is conditional on working exclusively with newly appointed FBI profiler Elizabeth Keen. A recurring narrative in the series is the development of the relationship between Reddington and Elizabeth Keen (portrayed by Megan Boone), which shifts from a professional collaboration to a more complex and emotionally layered association. Their connection, shaped by secrecy and ambiguity, contributes to the character development across the series. The character of Reddington has been the subject of critical analysis, with particular focus on James Spader’s interpretation. His performance has received several award nominations, including from the Golden Globe Awards, and has been identified as a significant element in the series' reception. The character is based on "Whitey" Bulger, an American organized crime boss who led the Winter Hill Gang, an Irish mob group.