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He also appears in [[Series/Fallout2024 the TV series]], and ''spoilers from it will follow''.
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The villain of the ''Dead Money'' arc. He is the Brotherhood of Steel elder who was once Veronica's mentor and got most of the chapter killed at the Battle of HELIOS One. It is revealed that after that when he went missing he found the legendary long-lost Sierra Madre casino and has gone insane(er) trying to access its vault ever since.
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The villain of the ''Dead Money'' arc. He is the Brotherhood of Steel elder who was once Veronica's mentor and got most of the chapter killed at the Battle of HELIOS One. It is revealed that after that when he went missing he found the legendary long-lost Sierra Madre casino and has gone insane(er) insane(r) trying to access its vault ever since.
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[[Characters/FalloutNewVegasTheCourier The Courier]] | [[Characters/FalloutNewVegasCompanions Companions]] | [[Characters/FalloutNewVegasNewCalifornia New California Republic]] | [[Characters/FalloutNewVegasCaesarsLegion Caesar's Legion]] | [[Characters/FalloutNewVegasTheStrip The Strip]] ([[Characters/FalloutNewVegasRobertEdwinHouse Robert Edwin House]]) | [[Characters/FalloutNewVegasSettlements Settlements]] | [[Characters/FalloutNewVegasOtherFactions Other Factions]] | [[Characters/FalloutNewVegasOtherCharacters Other Characters]] | '''Dead Money Characters''' | [[Characters/FalloutNewVegasHonestHearts Honest Hearts Characters]] | [[Characters/FalloutNewVegasOldWorldBlues Old World Blues Characters]] | [[Characters/FalloutNewVegasLonesomeRoad Lonesome Road Characters]]-]]]]]
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* ALighterShadeOfGray: Somewhat. [[spoiler:While he was part of the conglomerate that kickstarted the Great War in the first place]], his characterization in ''Dead Money'' establishes at least he has [[EvenEvilHasLovedOnes loved ones]] and ''somewhat'' of a conscience, although one that by all accounts developed too late.
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* SameCharacterButDifferent: ''New Vegas'' and the TV series were released over a decade apart, and Sinclair's characterization and appearance are drastically different between them.
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* AdaptationalUgliness: [[spoiler:In contrast to the dashing image seen around the ruined Sierra Madre, the TV show portrays Sinclair as older and decidedly fatter.]]
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* TooCleverByHalf: [[spoiler:As it turns out, House's chiding in [[Series/Fallout2024 the TV show]] about Sinclair's inability to run a casino proved prophetic, given that nearly everything to do with the Sierra Madre comes back to haunt him.]]
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* OnlyKnownbyTheirNickname: Within the TV show, he's only addressed as Freddy-boy.
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* OnlyKnownbyTheirNickname: OnlyKnownByTheirNickname: Within the TV show, he's only addressed as Freddy-boy.
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* OnlyKnownbyTheirNickname: Within the TV show, he's only addressed as Freddy-boy.
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* YouDontLookLikeYou: The glass art in Dead Money depicts him as a slim suave type, but in the TV show he's shown as both much older and overweight.
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* MouthOfSauron: [[spoiler:He was Big MT's representative in the meeting between corporations where they were discussed how to set off the Great War, though it's not clear this meant that he was the actual head or merely their voice at the table]].
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* UnwittingPawn: Twice. Once by [[spoiler:Dean Domino and Vera Keyes]]. The second time by [[spoiler:the scientists of Big Mountain, who hid from him the extent of the experiments they would conduct on the Villa and have been observing the area for the whole period]].
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* UnwittingPawn: Twice. Once by [[spoiler:Dean Domino and Vera Keyes]]. The second time by [[spoiler:the scientists of Big Mountain, who hid from him the extent of the experiments they would conduct on the Villa and have been observing the area for the whole period]]. However, the TV series portrays him as Big MT's representative at a meeting between the various corporations of the time implying that he actually did have some level of authority over them.
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He also appears in ''Series/Fallout2024'', and ''spoilers from that show will follow.''
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* WalkingSpoiler: He's both an important figure in ''Dead Money'' and a part of [[Series/Fallout2024 the TV show's]] reveal, and it's nigh-impossible to discuss him without spoilers.
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* AffablyEvil: [[spoiler:What his characterization in ''Dead Money'' and the Amazon Prime series adds up to: the former depicts him as a nice guy that tried to keep up with everyone and paid well for the services, and the latter shows he was one of the men that orchestrated the Great War.]]
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* RedemptionEqualsDeath: Sort of, if you don't take the ''Series/Fallout2024'' reveal into consideration - [[spoiler:On the night the bombs hit, he realised he couldn't kill Vera, who confessed to her role, and went down to the vault to disable the trap. He died trying.]]
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* RedemptionEqualsDeath: Sort of, if you don't take within the ''Series/Fallout2024'' reveal into consideration context of ''Dead Money'' alone - [[spoiler:On the night the bombs hit, he realised he couldn't kill Vera, who confessed to her role, and went down to the vault to disable the trap. He died trying.]]
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He also appears in ''Series/Fallout2024'', and ''spoilers from that show will follow.''
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* AssholeVictim:[[The Prime series reveals that he was complicit with Vault-Tec in kickstarting the Great War. This makes Dean's plot against him oddly karmic and his death all the more deserving.]]
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* AssholeVictim:[[The AssholeVictim: [[spoiler:The Prime series reveals that he was complicit with Vault-Tec in kickstarting the Great War. This makes Dean's plot against him oddly karmic and his death all the more deserving.]]
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* RedemptionEqualsDeath: Sort of. [[spoiler:On the night the bombs hit, he realised he couldn't kill Vera, who confessed to her role, and went down to the vault to disable the trap. He died trying. Then subverted. His role in kickstarting the Great War ensures that his attempt to save Vera does nothing to erase his heinous actions.]]
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* RedemptionEqualsDeath: Sort of. of, if you don't take the ''Series/Fallout2024'' reveal into consideration - [[spoiler:On the night the bombs hit, he realised he couldn't kill Vera, who confessed to her role, and went down to the vault to disable the trap. He died trying. Then subverted. His role in kickstarting the Great War ensures that his attempt to save Vera does nothing to erase his heinous actions.]]]]
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* RightForTheWrongReasons: [[spoiler:As reveled in the Prime series, Sinclair was absolutely a bastard who was fine with scheming to kickstart the Great War with Vault-Tec without any remorse.]] Dean himself doesn't know this, however, and hates Sinclair purely because of his PsychologicalProjection and envy of Sinclair being a positive person.
* AssholeVictim:[[The Prime series reveals that he was complicit with Vault-Tec in kickstarting the Great War. This makes Dean's plot against him oddly karmic and his death all the more deserving.]]
* FatBastard: [[spoiler:Shown to be a fat old man in the Prime series when he was still alive and perfectly fine with scheming to kickstart the Great War with the rest of Vault-Tec.]]
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* NiceGuy: For all his faults with Dean and Vera, it was noted by many people who were serious about working for him that he was a really nice guy. He would often check on people, see how they were doing, and it was noted he paid really well. Even his refusal to allow contraband items came from a place of good intentions.
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* NiceGuy: For all his faults with Dean and Vera, it was noted by many people who were serious about working for him that he was a really nice guy. He would often check on people, see how they were doing, and it was noted he paid really well. Even his refusal to allow contraband items came from a place of good intentions. [[spoiler:Subverted with the reveal in the Prime series that he was well aware of the Great War due to being one of its architects.]]
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* RedemptionEqualsDeath: Sort of. [[spoiler:On the night the bombs hit, he realised he couldn't kill Vera, who confessed to her role, and went down to the vault to disable the trap. He died trying.]]
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* RedemptionEqualsDeath: Sort of. [[spoiler:On the night the bombs hit, he realised he couldn't kill Vera, who confessed to her role, and went down to the vault to disable the trap. He died trying. Then subverted. His role in kickstarting the Great War ensures that his attempt to save Vera does nothing to erase his heinous actions.]]
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* UnwittingInstigatorOfDoom: It's doubtful that he knew what [[spoiler: Big Mountain had in store for the Villa.]]
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* UnwittingInstigatorOfDoom: It's doubtful that he knew what [[spoiler: Big Mountain had in store for the Villa. Possibly subverted with the Prime series revealing he was far closer to Big MT than indicated.]]
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* GreaterScopeVillain: The Prime series reveals that [[spoiler:alongside House, Vault-Tec and other pre-war corporations he was one of the architects of the Great War]].
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That's just a case of the Big Bad being defeated
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* AssholeVictim: his defeat by being locked into vault is well earned.
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* AssholeVictim: his defeat by being locked into vault is well earned.
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* BerserkButton: He cannot stand anyone who acts like they're better than him and absolutely despises anyone who get the upper hand on him.
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* BerserkButton: He cannot stand anyone who acts like they're better than him and absolutely despises anyone who get the upper hand on him. This has interesting gameplay ramifications: [[spoiler:if you take a Speech check option during your first interaction with him, he ''notices'', thinks you're trying to play a fast one on him, and ''will'' betray you at a critical moment.]]
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* JerkWithAHeartOfJerk: If you inform him that you know of his name from Veronica, he will briefly seem overjoyed, but only because he's simply surprised she survived and not because he finally gets great news that his former daughter figure is still around. He quickly changes the topic to his bitterness over losing Helios One and hatred of the NCR.
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The likeness is much closer to Cab Calloway than Sammy Davis Jnr.
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* NoCelebritiesWereHarmed: According to a portrait, he looked much like Sammy Davis Jr. before becoming a ghoul.
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* NoCelebritiesWereHarmed: According to a portrait, he looked much like Sammy Davis Jr. [[Music/CabCalloway Cab Calloway]] before becoming a ghoul.
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* KickedUpstairs: The reason why he was selected to head the Mojave expedition, was because he was constantly butting heads with the other, more conservatives Elders over the Codex. Sending him to establish a new chapter in the far frontier was basically their way to get him out of their hair.
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* KickedUpstairs: The reason why he was selected to head the Mojave expedition, expedition in the first place, was because he was constantly butting heads with the other, more conservatives Elders over their orthodox adherence to the Codex. Sending him to establish a new chapter in the far frontier was basically their way to get him out of their hair.
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* KickedUpstairs: The reason why he was selected to head the Mojave expedition, was because he was constantly butting heads with the other, more conservatives Elders over the Codex. Sending him to establish a new chapter in the far frontier was basically their way to get him out of their hair.
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* AmbiguouslyBi: [[spoiler: It's implied that she is Veronica's ex-girlfriend]], but she may also show some affection (although not explicitly romantic) towards the courier, regardless of gender.
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* AmbiguouslyBi: [[spoiler: It's implied that she is Veronica's ex-girlfriend]], but she may also show some affection (although not explicitly romantic) towards the courier, Courier, regardless of gender.
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* DemolitionsExpert: The only follower in the entire game who's proficient with explosives. Unfortunately, since access to explosive weapons is limited during the DLC, the only time he'll display this proficiency is when he tricks the courier with a pressure sensitive mine, in order to gain the upper hand over them.
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* DemolitionsExpert: The only follower in the entire game who's proficient with explosives. Unfortunately, since access to explosive weapons is limited during the DLC, the only time he'll display this proficiency is when he tricks the courier Courier with a pressure sensitive mine, in order to gain the upper hand over them.
