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There's a simple way, it's said, to gauge whether your life has been a fulfilling one - that being that if it were made into a book, would anyone want to read it? By that criteria, Lee Jordan has definitely led a fulfilling life - as one of the more prolific members of the ACME Detective Agency, he solved over one hundred cases in the span of four years; he's seen more of the world in the last few years than most see in their entire lifetimes, and at some point in the past, he was assigned to the Carmen Sandiego case - culminating in an incident in Morocco that resulted in Lee becoming the only ACME agent to officially capture her (that is, until local authorities botched the arrest, to hear him tell it). Intelligent and highly efficient, Lee Jordan is a hell of a detective, and he can be said to have lived an exceedingly fulfilling life - one that would certainly make for an interesting book, if nothing else.
Shame that he doesn't necessarily see it that way, because the title of that book might as well be Why Won't Senpai Notice Me?: A Memoir.
Lee is a highly motivated individual naturally, driven by a desire to be the best at anything and everything he does; while not a bad thing on its own, with Lee it's more or less a compulsion, more of a need than a want at its core, and as a need it's almost completely insatiable. As far as he's concerned, nothing is ever going to be "good enough"; there's always something else, another achievement to gain or another prize to win, and because nothing he does is ever going to be good enough in his own eyes, he has a tendency to doubt whether the people above him are going to see him as being good enough, either. At one point during his debut episodes, he's seen talking to himself when he's alone, muttering about how he needs to prove that he's "indispensable"; he also gets extremely angry at implications that he isn't valuable, such as being referred to as an "errand boy" - after all, errand boys are a dime a dozen. This leads to a tendency toward overcompensation (after all, if he's doing more than anyone else, better than anyone else, then he can't possibly be disposed of or replaced) and an utter refusal to accept help from others, even when he could probably use it.
Fortunately enough, however, Lee is incredibly talented, enough so that outside help isn't often required: outside of the general intellectual gifts that led him to become such a good detective in the first place, he can be inferred to speak several languages, he knows how to fly a plane, and he's good with creating and building various mechanical devices and weapons; physically speaking, he's powerfully athletic, the result of physical training and his incredibly active lifestyle. Most of his life has been such that true failure just isn't something that happens to him - something that he's never hesitated to point out, because modesty isn't among his many talents.
In fact, there are a lot of basic social skills that aren't; Lee has no sense of personal space or boundaries once he's decided he finds someone interesting, often standing far too close for comfort, reaching out to touch their hair or their face and generally just coming across as a tremendous creeper. He flirts quite a bit, but the flirting has about all the subtlety of a sack of bricks to the face and about as much finesse, and even when he isn't creeping on a girl somehow, normal conversations just aren't something he does well - he always seems like he would rather be just about anywhere else or just generally doing something more important than just standing around talking, and he becomes easily frustrated and agitated when things stop going his way conversationally.
But if it's just a matter of dealing with a temporary issue, interpersonal or otherwise, Lee is generally able to handle it; true, he usually requires a cooldown period where he can just skulk off to be alone, and he may take out his frustration on an inanimate object or six, but he can usually calm himself down well enough to get back to work. If it's a matter of serious failure or shortcomings, however, especially in front of a supervisor or someone he looks up to...well...
While one could say that Lee Jordan has anger issues and be entirely correct, saying that would also put one in the running for Understatement of the Century; the abovementioned compulsion toward being the best and proving himself indispensable flares up with a vengeance, and the tendency toward overcompensation drives him to regain control over his situation by any means possible. To his credit, he usually starts out by exhibiting behaviors that he thinks will be considered "acceptable" to the person he's trying to impress or get back in the favor of; however, he goes about it in ways that are excessive, fail to address or fix the initial problem, or otherwise are just downright bizarre - and then when this inevitably fails to meet with approval, he lashes out. The results of this latter behavior aren't minor issues, either: it tends to result in property damage (he has a particular fondness for literally crashing gates with his car), flagrant disregard for human life (he's nearly killed the protagonists - who are for all intents and purposes a pair of children - on several occasions), hostage-taking, threatening with weapons, incidents that may or may not result in massive explosions...and absolutely none of it is his fault. After all, being the best means that he can't afford to be wrong, and any massive failures and shortcomings are always, always someone else's fault.
It's interesting to note that this seems to be the case with his capture of Carmen - what happened in Morocco is never explained in detail, but he explicitly says that he caught her; he then goes on to explain that the local authorities screwed it up somehow. However, when he discusses it later, he can't seem to keep his story straight: sometimes he caught her once but she got away from him; sometimes he's never caught her but he'll catch her this time; sometimes he's caught her multiple times...it seems to fluctuate based on his mood at the moment, and as such it's hard to tell whether that capture was something that was legitimately unfairly botched for him, or if he's simply trying to cover (albeit a bit badly) for something that may have been his own mistake.
At any rate, the point is that no one likes Lee when he's angry, and with good reason; he becomes incredibly violent and willing to utterly throw any caution and care he may have had to the wind, and he becomes a tremendous winner to deal with overall. With all of that in mind, though, it quickly becomes rather clear that the horrendous interpersonal skills is due in some part at least to a massive lack of empathy; said lack of empathy is also why his attempts at rectifying his failures are so strange. He understands that he's seen as having failed, but he doesn't always understand why, especially when the reason why is more abstract or deals with moral standings rather than purely objective situations. This results in massive amounts of frustration with his situation; over the course of his career with ACME, he seems to have at least had some sort of outlet for it in that he could throw himself into his work. However, after a while that failed to be properly fulfilling, for many reasons - he was no longer working on the Carmen Sandiego case following whatever happened in Morocco, and his other successes had dulled the challenge for him, rendering him arrogant, bitter and more than a bit bored. The only thing that interested him was catching Carmen; she'd always provided a sense of personal intrigue for him, and once he was given a chance to get back on the case involving her, he leapt at it with a vengeance.
What no one at ACME was predicting was the fact that Lee had apparently grown tired of doing things their way, and would take the opportunity to join Carmen instead of securing a second capture.
At his current canonpoint, that's more or less where Lee stands; he's working with Carmen now, for the side of...uh, thievery, rather than good. While he does enjoy the challenge, this arrangement also has the unfortunate effect of removing any support network or proper guidance that he may have had back in the detective agency - he has nowhere to channel any anger or frustration that he experiences, leaving him to either attempt to contain it (which tends to end in hideous amounts of failure and, well, more anger and frustration) or overcompensating in order to get rid of it. No longer explicitly being one of the "good guys" also means that Lee is no longer restrained by things like expected morality or any sort of proper protocol, making his fits of violence all the more potentially explosive and destructive. Carmen took him on under the impression that she was getting a protégé; what she got was an intensely unstable wreck that strives for validation through his accomplishments and has no idea how to not be a complete psychopath about it.
For the time being, however, he's still trying to get senpai to notice him, if you will - to prove himself completely indispensable, to be the very best. The issue is that no one has noticed that they're making a supervillain in the process.
Shame that he doesn't necessarily see it that way, because the title of that book might as well be Why Won't Senpai Notice Me?: A Memoir.
Lee is a highly motivated individual naturally, driven by a desire to be the best at anything and everything he does; while not a bad thing on its own, with Lee it's more or less a compulsion, more of a need than a want at its core, and as a need it's almost completely insatiable. As far as he's concerned, nothing is ever going to be "good enough"; there's always something else, another achievement to gain or another prize to win, and because nothing he does is ever going to be good enough in his own eyes, he has a tendency to doubt whether the people above him are going to see him as being good enough, either. At one point during his debut episodes, he's seen talking to himself when he's alone, muttering about how he needs to prove that he's "indispensable"; he also gets extremely angry at implications that he isn't valuable, such as being referred to as an "errand boy" - after all, errand boys are a dime a dozen. This leads to a tendency toward overcompensation (after all, if he's doing more than anyone else, better than anyone else, then he can't possibly be disposed of or replaced) and an utter refusal to accept help from others, even when he could probably use it.
Fortunately enough, however, Lee is incredibly talented, enough so that outside help isn't often required: outside of the general intellectual gifts that led him to become such a good detective in the first place, he can be inferred to speak several languages, he knows how to fly a plane, and he's good with creating and building various mechanical devices and weapons; physically speaking, he's powerfully athletic, the result of physical training and his incredibly active lifestyle. Most of his life has been such that true failure just isn't something that happens to him - something that he's never hesitated to point out, because modesty isn't among his many talents.
In fact, there are a lot of basic social skills that aren't; Lee has no sense of personal space or boundaries once he's decided he finds someone interesting, often standing far too close for comfort, reaching out to touch their hair or their face and generally just coming across as a tremendous creeper. He flirts quite a bit, but the flirting has about all the subtlety of a sack of bricks to the face and about as much finesse, and even when he isn't creeping on a girl somehow, normal conversations just aren't something he does well - he always seems like he would rather be just about anywhere else or just generally doing something more important than just standing around talking, and he becomes easily frustrated and agitated when things stop going his way conversationally.
But if it's just a matter of dealing with a temporary issue, interpersonal or otherwise, Lee is generally able to handle it; true, he usually requires a cooldown period where he can just skulk off to be alone, and he may take out his frustration on an inanimate object or six, but he can usually calm himself down well enough to get back to work. If it's a matter of serious failure or shortcomings, however, especially in front of a supervisor or someone he looks up to...well...
While one could say that Lee Jordan has anger issues and be entirely correct, saying that would also put one in the running for Understatement of the Century; the abovementioned compulsion toward being the best and proving himself indispensable flares up with a vengeance, and the tendency toward overcompensation drives him to regain control over his situation by any means possible. To his credit, he usually starts out by exhibiting behaviors that he thinks will be considered "acceptable" to the person he's trying to impress or get back in the favor of; however, he goes about it in ways that are excessive, fail to address or fix the initial problem, or otherwise are just downright bizarre - and then when this inevitably fails to meet with approval, he lashes out. The results of this latter behavior aren't minor issues, either: it tends to result in property damage (he has a particular fondness for literally crashing gates with his car), flagrant disregard for human life (he's nearly killed the protagonists - who are for all intents and purposes a pair of children - on several occasions), hostage-taking, threatening with weapons, incidents that may or may not result in massive explosions...and absolutely none of it is his fault. After all, being the best means that he can't afford to be wrong, and any massive failures and shortcomings are always, always someone else's fault.
It's interesting to note that this seems to be the case with his capture of Carmen - what happened in Morocco is never explained in detail, but he explicitly says that he caught her; he then goes on to explain that the local authorities screwed it up somehow. However, when he discusses it later, he can't seem to keep his story straight: sometimes he caught her once but she got away from him; sometimes he's never caught her but he'll catch her this time; sometimes he's caught her multiple times...it seems to fluctuate based on his mood at the moment, and as such it's hard to tell whether that capture was something that was legitimately unfairly botched for him, or if he's simply trying to cover (albeit a bit badly) for something that may have been his own mistake.
At any rate, the point is that no one likes Lee when he's angry, and with good reason; he becomes incredibly violent and willing to utterly throw any caution and care he may have had to the wind, and he becomes a tremendous winner to deal with overall. With all of that in mind, though, it quickly becomes rather clear that the horrendous interpersonal skills is due in some part at least to a massive lack of empathy; said lack of empathy is also why his attempts at rectifying his failures are so strange. He understands that he's seen as having failed, but he doesn't always understand why, especially when the reason why is more abstract or deals with moral standings rather than purely objective situations. This results in massive amounts of frustration with his situation; over the course of his career with ACME, he seems to have at least had some sort of outlet for it in that he could throw himself into his work. However, after a while that failed to be properly fulfilling, for many reasons - he was no longer working on the Carmen Sandiego case following whatever happened in Morocco, and his other successes had dulled the challenge for him, rendering him arrogant, bitter and more than a bit bored. The only thing that interested him was catching Carmen; she'd always provided a sense of personal intrigue for him, and once he was given a chance to get back on the case involving her, he leapt at it with a vengeance.
What no one at ACME was predicting was the fact that Lee had apparently grown tired of doing things their way, and would take the opportunity to join Carmen instead of securing a second capture.
At his current canonpoint, that's more or less where Lee stands; he's working with Carmen now, for the side of...uh, thievery, rather than good. While he does enjoy the challenge, this arrangement also has the unfortunate effect of removing any support network or proper guidance that he may have had back in the detective agency - he has nowhere to channel any anger or frustration that he experiences, leaving him to either attempt to contain it (which tends to end in hideous amounts of failure and, well, more anger and frustration) or overcompensating in order to get rid of it. No longer explicitly being one of the "good guys" also means that Lee is no longer restrained by things like expected morality or any sort of proper protocol, making his fits of violence all the more potentially explosive and destructive. Carmen took him on under the impression that she was getting a protégé; what she got was an intensely unstable wreck that strives for validation through his accomplishments and has no idea how to not be a complete psychopath about it.
For the time being, however, he's still trying to get senpai to notice him, if you will - to prove himself completely indispensable, to be the very best. The issue is that no one has noticed that they're making a supervillain in the process.