MBTI TYPE: INTJ
Major spoilers below. Leonard really gives the impression of being an ISTJ for a huge section of the film, in that he has worked in one profession for a long time and become an expert at it, and has no great desire to do anything else with his life. He is exact, meticulous, and attentive to the finer details of his craft, patiently taking apart suits and making precise cuts. However… in the film’s twist, we learn most of this is a front. Leonard has been playing a ‘long game,’ in which he intuitively figured out that Mable, his secretary, was selling information about the mob to the FBI, and then figured out a long con in which he made up a rival agency called ‘The Outfit’ in order to ensure that she could get away with her life. He constructed most of the events of the film, including the death of Mable’s mob boyfriend, provoked violence between two rival gangs, and then helps them eliminate one another in a brutal shoot-out, so that Mable can get away with the money and flee to safety abroad (and take all the trips she has always wanted to take). He admits to having planned everything meticulously and most of it unfolds exactly the way he foresaw it… except that someone isn’t dead and attacks him, catching him off guard and forcing him to kill them. He is almost overpowered in this instance, because of his low Se inability to be attentive to his environment or react quickly to a threat; it’s only his assassin skills that saves his life. Elsewhere, Leonard shows a TJ tendency to look the other way, to state the facts, and to remain untouched emotionally by other people’s problems and their experiences. He is a successful businessman who minds his own, and who figures out how to strategically get rid of threats by thinking logically at each twist and turn of the plot, even when it comes to making up lies to convince gangsters to turn on each other and/or to pretend to be their friend long enough to get Mable off the hook. He admits that he is the mole quite early on to a gangster, who laughs in his face and says that’s stupid, he’s “just” a tailor (“cutter,” he corrects them). He does care deeply for Mable and does what he can to protect her; the loss of his family also caused him to abandon his career as a hit man/gangster, and create a new life for himself in Chicago.
Enneagram: 9w1 sp/so
Leonard has an almost unflappable sense of calm and can get anyone to quiet down and go along with him, simply by refusing to panic, get upset, or show any emotions beyond his basic instinct and desire to protect Mable. As the story unfolds, we learn that he was actually a hit man for the mob and spent most of his time killing people, but that he decided he wanted to be “good” and has given up that lifestyle. He has many conversations with Mable about being a “gentleman,” and wanting things to be perfect—including his little tics such as needing to fold handkerchiefs exactly and precisely in a square. He teases her mildly about doing it improperly and has a compulsive need to fix it, but has a 9ish ability to look the other way when dealing with bad behavior in others and going along with things to keep them calm and unruffled. He seems nonplussed about having to “start over” somewhere else, since he knows he can easily do it, and he has no real attachment to money, since he leaves Mable to take it all and escape.
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