Season: 2-6, Episodes: 19, Faction: The Others/Himself
Charles Widmore was a former leader of the Others, a wealthy industrialist and the father of Penelope Widmore and Daniel Faraday. He had a long-running and mysterious rivalry with Benjamin Linus (also a former leader of the Others) over control of the Island. The expedition of the freighter Kahana failed to return the Island to his possession.
For unknown reasons, Ben claimed that he was unable to kill Widmore even when given the opportunity, and that they both knew it. This presumably relates to his previous citation of rules governing the two’s dispute, which he said Widmore changed upon his mercenary Keamy killing Ben’s daughter Alex. As a response to this, Ben told Charles that he would find and kill his daughter, Penny. Furthermore, Widmore was apparently plotting to kill Ben, a “common interest” he had with Sun-Hwa Kwon until she learned that Ben’s actions on the Island had not resulted in her husband’s death. It is unknown how either of these facts relates to the rules, or their being “changed”.
In 2007, Widmore finally returned to the Island in a submarine after claiming to have been invited by Jacob, who “convinced [him] of the error of [his] ways” not long after the freighter was destroyed and told him everything he needed to know to stop the Man in Black from leaving. He brought Desmond Hume back with him, as a last resort in case all of Jacob’s candidates died. Widmore was eventually shot to death by Ben in his secret room in front of the Man in Black.
After the rescue of the Oceanic Six
4×09 – The Shape of Things to Come
Sometime after the Oceanic Six were rescued, Widmore was confronted by Ben in his London penthouse. Widmore looked tired and unshaven, and when asked by Ben when he started “sleeping with a bottle of scotch by the bed”, he replied “When the nightmares started.” Widmore assumed that Ben had come to kill him, but Ben replied, “We both know I can’t do that.” The two argued about who was responsible for the death of Alex. Widmore claimed that everything Ben had he took from him. Ben threatened to kill Widmore’s daughter, Penelope, whom Widmore indicated would be never found. Widmore claimed the Island was his but Ben asserted that he would never find it. Widmore mused that the hunt was on for both of them. (“The Shape of Things to Come”)
It was shortly after this that Widmore’s surveillance in Tunisia caught John Locke lying in the desert after having been transported there. Widmore had cameras fixed on this spot because he somehow knew it to be “the exit” from the Island. Widmore’s associates found Locke and brought him to a field hospital. After he awoke, Locke found himself face-to-face with Widmore. Widmore reminded Locke of their meeting in 1954, which for Locke had only been 4 days ago. Widmore told Locke of an approaching war and agreed to help him in his quest to bring the Oceanic Six back to the Island.
He gave Locke his cover identity of Jeremy Bentham and provided Locke with the services of Matthew Abaddon, as well as dossiers on the whereabouts and status of the Oceanic Six. Before they parted Locke recalled that Widmore had previously wanted to kill everyone of the Island and was now helping him, but Widmore – likely recalling his conversation with Jacob – assured Locke this was no longer the case. (“The Life and Death of Jeremy Bentham”)
Some time later, Sun approached Widmore in London. At first he pretended to merely know her through his connection with her father. However, Sun confronted him, indicating that he knew she was part of the group that had been on the Island and that they were lying about it. Sun then offered to collaborate with Widmore. He asked her why she would want to help him, but she didn’t answer. (“There’s No Place Like Home, Part 2”)
5×01 – Because You Left
While Sun was checking in for her flight to Los Angeles, the attendant asked her to hold for a moment, then escorted her to a room where the door was locked behind her. Widmore appeared and scolded her for approaching him in broad daylight in front of his colleagues. He brought up her statement about their common interests, and asked what they are. She told him plainly, “To kill Benjamin Linus.” (“Because You Left”)
5×03 – Jughead
Shortly thereafter, in his office, Widmore was surprised by an unexpected visitor: Desmond Hume, whom he had not seen in around seven years. Desmond demanded to know where he could find Daniel Faraday’s mother. When Widmore appeared confused, Desmond revealed that he knew Widmore had subsidized Faraday’s research at Oxford for about ten years before he sent Daniel to the Island on the freighter, and also paid for Theresa’s medical support. Widmore attempted to find out whether Penny was safe, yet Desmond insisted on a location for Faraday’s mother.
Widmore eventually gave Desmond an address in Los Angeles, yet warned Desmond that he was “getting (himself) involved in something that goes back many many years.” and begged Desmond to keep himself and Penny out of it by hiding. (“Jughead”)
5×12 – Dead Is Dead
A few days later, as Widmore was walking out of Widmore Industries, Ben phoned him from a marina in Long Beach. He told Widmore that he was about to return to the Island, to which Widmore replied that the Island wouldn’t let him. The conversation ended with Ben reminding Widmore that he was going to murder his daughter Penelope, and that he was staring at Desmond’s boat. Widmore responded, “You wouldn’t dare,” as Ben hung up. Ben ended up shooting Desmond, but hesitated to kill Penny, giving the injured Desmond enough time to stop him. (“Dead Is Dead”)
5×14 – The Variable
After this, Charles traveled to Los Angeles and appeared at the Long Beach hospital where Desmond was being treated for his gunshot wound. Here, he met up with his old friend, Eloise Hawking, who informed him that Desmond was recovering, to which he indicated that he was pleased, and Penny was inside and that he should go see her. Charles stated that he had sacrificed his relationship with Penny. It is then revealed that Eloise knew that sending Daniel to the island would lead to his death, stating that it was she who had made a sacrifice. Charles interrupts her saying “He was my son too, Eloise.” Angered by this remark, Eloise slapped Charles in the face and walked off. (“The Variable”)