|“||You know, I really can't work out whether you're being sarcastic or if you're really, really dim.||„|
|~ Sinclair can't work it out if Hughes is being sarcastic or not|
Sinclair is the main antagonist of the 2012 film Home Alone: The Holiday Heist.
He was portrayed by Malcolm McDowell, who also played Alex DeLarge in A Clockwork Orange, Caligula in Caligula, Kesslee in Tank Girl, Lord Maliss in Happily Ever After, Tolian Soran in Star Trek: Generations, Daniel Linderman in Heroes, Andrej Evilenko in Evilenko, Gangster in Gangster No. 1, Captain Von Berkow in The Passage, The Shaman in the Aladdin TV series, Colonel F. E. Cochrane in Blue Thunder, Arnold Gundars in I Spy, Mad Mod in Teen Titans, Marcus Kane in Doomsday, Tower in Phineas and Ferb, and Geoffrey Tolwyn in the Wing Commander video game series.
Sinclair is an art thief who is in search of the lost Edvard Munch's painting The Widow because his great-grandmother and her family is painted on it. After spending decades to search it along with his henchwoman Jessica, he finally finds the painting in the former house of a legendary gangster named Jimmy "Dead Leg" Gravano. He hires the safecracker Hughes to burgle the house, which is currently occupied by the Baxter family.
While the family leaves their home to go shopping, Sinclair, Jessica and Hughes break into the house and begin to open the safe containing the painting. However, the Baxters return home before the thieves get it, forcing them to quickly flee.
The following day, Sinclair encounters Finn, the youngest child of the Baxter family, in the street and the boy decides to follow him. He overhears Sinclair and his two henchmen discussing of the plans to break into his house a second time, therefore Finn returns home and sets up numerous booby traps around the house. Afterwards, the trio comes to the house and triggers the traps one by one. However, the thieves finally manage to capture Finn and then they open the safe once again, but Sinclair has to fight with Hughes who wants to sale the painting instead of keeping it. Finn later manages to escape and triggers a trap that locks the thieves, and shortly after the police arrive to arrest them.
The three thieves are last seen having their mugshots at the police station.