* AlternativeCharacterInterpretation: Donald Love didn't have much CharacterDevelopment in ''III'' and ''Vice City'', but he's really weird in this game.
** Toni Cipriani a righteous man who delights only commit atrocities because just follow orders. Or he is a PsychoForHire? Toni is probably the protagonist who committed the greatest atrocities canonical, including killing a man with an ax and carrying his remains to a butcher shop, and this was done intentionally and not to follow an order, without mention several atrocities that go by Donald Love and Ned Burner's orders. While still repents of his sins in a confessional, he never sought redemption when he bombed the area of Fort Staunton.
* CompleteMonster: Donald Love somehow manages to reach a special level of evil despite living in a Crapsack World populated with gangsters, [[SerialKiller serial killers]], and [[AxCrazy psychopaths]]. Introduced in ''VideoGame/GrandTheftAutoIII'', Love at first seems fairly standard for the series, arranging a gang war between TheYakuza and TheCartel just to lower property values. Though, at the time it was hinted he had [[ImAHumanitarian more sinister appetites]]. This is eventually confirmed in this game, where he's shown feasting on corpses and sending Toni Cipriani to collect bodies for him to devour. Aligning himself with [[TheMafia the Leone crime family]], Love runs in the race for mayor, sending Toni Cipriani out to murder his rival's campaigners. Losing his fortune in his failed campaign, Love makes plans to regain his fortune, with his first step being to [[BastardUnderstudy murder his mentor]], real-estate tycoon Avery Carrington, in order to steal his city development plans. He then has Toni recover Carrington's body to cannibalize later. Love's worst crime, however, is masterminding the deaths of thousands of people through the bombing of the heavily-populated Fort Staunton city district, just so he can make money off of redeveloping the district. A thoroughly depraved man, Love would stoop to any low imaginable to fill his pockets or glorify his ego.
* MoralEventHorizon: Paulie Sindacco intersects with the attempted murder of Salvatore, sending his henchmen to take him to the crusher.
** Toni's mother has probably crossed with the attempted murder of her own son for not being a man.
* NightmareFuel: Several thing that makes Toni Cipriani is pure Nightmare Fuel. This is evident in the mission "Dead Meat", where he kills a man with an ax and dismembered him, and takes over his remains to a butcher for his remains to be sold.
* ThatOneLevel: The game ramps up the difficulty for obtaining some of the hidden packages to an almost insane level. A hidden package located on top of a gas station roof in Portland is considered particularly difficult to reach, and even GuideDangIt assistance if unhelpful.
* TheScrappy: Toni's mother is this to some fans.