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Simon Peter Gruber is a fictional character created by John McTiernan and Jonathan Hensleigh and is the main antagonist from the 1995 action film Die Hard With a Vengeance portrayed by Jeremy Irons. The character is depicted as the younger brother of Hans Gruber, the primary antagonist of the first Die Hard film. Simon seeks revenge on John McClane for the death of his brother and puts McClane through different tasks around New York City as Simon enacts different terrorist plots.

Fictional character biography
Simon Peter Gruber is the younger brother of famed East-German terrorist Hans Gruber. Hans was killed by John McClane at the Nakatomi Plaza in Los Angeles during Gruber's attempts to steal $640 million in bearer bonds. Fuelled with rage from his brother's death, Simon developed a plan to steal $140 million in gold bullion from the New York Federal Reserve Bank. Inspired by his brother's efforts of deception, Gruber formulated a wild goose chase for the NYPD to distract them from the heist by citing revenge against McClane as his primary motivation.

Simon's plan began with bombing a department store in New York City. Simon calls NYPD Inspector Walter Cobb claiming responsibility, and requesting to play a game of "Simon Says" with McClane, who has relocated back to New York after separating from his wife - Holly Gennaro. Gruber states that if McClane doesn't participate, another bomb will be detonated. Gruber makes McClane wear a racially charged hate sign in Harlem. McClane is noticed by electric store owner, Zeus Carver, who intervenes before McClane can be attacked by a street gang. Irritated that Carver interfered with his plan, Gruber quickly forces Zeus to partner with McClane and participate in Simon's game. Simon continues to send McClane and Carver on a wild goose chase throughout New York whilst he empties the gold into dump trucks and flees to Canada. Simon informs the NYPD that the gold is located on a ship off of the coast of Long Island which he intends to detonate. However, it is uncovered that the boat simply contains scrap metal. McClane and Carver attempted to attack the boat, but were instead kidnapped by Gruber and handcuffed to a pole next to the bomb. Simon reveals that he never actually liked his brother, but will kill McClane anyways for interfering with his plans before leaving for Canada with his henchmen.

Simon's celebration is cut short when he is interrupted by McClane, Carver and multiple police officers. McClane was able to locate Gruber due to him leaving behind a bottle of asprin for his migraines on the boat, which had the location Simon intended to flee to on it. Simon and his girlfriend Katya activate a helicopter in another attempt to kill McClane. McClane shoots a transformer on a power line, which sends a wire into the helicopter blades, killing Simon.

Comparisons to The Riddler
Due to the nature of Simon's plan for revenge against McClane, many fans have noted the similarities between Simon and Edward Nygma / The Riddler.