This is one bit that I can't wrap my around with 90s and current Trek. Other than Ferengi, there really isn't any Mudd like characters. I've love to see a Neal Caffrey (White Collar) like character in Star Trek. I get the impression from current Trek that if you didn't make it into Starfleet, then you have to hustle. There should be a lot of con artists in the Trek universe. And there should be a ton of opportunities to take advantage of the Dunning-Kruger Effect, which should be ripe in the ranks of Starfleet.
The quarter-Betazoid guy from the Price? Those guys in VOY who scammed people in the Delta Quadrant by pretending to be Janeway and Tuvok (I think the Tuvok impersonator was played by the same actor who played Tuvix?) That guy from the...was it the 21st century?....who stole that time machine and pretended to be a time traveller from the future instead? Though...yeah I wouldn't mind a Neal Caffrey-like character in Trek...provided the actor is as hot as Matt Bomer ;-)
No money for humans in a free society. No money internally for the Federation. If you ask the Federation for anything with in reason, they'll probably just give it to you. Matt McCoy was not a con man. He was a business man with a secret, no worse than Picard who relied on Deanna's intuition on the bridge, without telling anyone that they were being probed hard and put away wet.
You're forgetting about the bit when he and the Ferengi come up with a scheme to trick the Barzan into going with Matt McCoy's team. He may not have been a con man every day, but he was that day.
Kivas Fajo. Guy from The Price. Other Elaurian in DS9. Rasmussen. Lorca. Peanut Hamper. If conmen are less frequent in Kurtzmantrek than Bermantrek it’s only cause it was more episodic.
I prefer the idea that most people are like Bashir's dad, just regular guys doing regular jobs. Maybe Starfleet is the military/police/NASA/etc all rolled into one but surely it's not so all encompassing that EVERY job belongs to them. There's those civilain mates of Picard who want to build underwater cities. There's a Federation Naval Patrol that Paris wanted to join. There's that Paul Mannheim guy who made that time experiment in the first season of TNG. Kasidy Yates flies around delivering stuff in her freighter. People like Leah Brahms and Carol Marcus work with Starfleet. But I love Bashir's dad, that he's done a bunch of jobs and nothing really stuck but he moves on and tries something else. Not everyone is going to be a Starfleet officer of even a savant like Rom designing cloaked mines and that's okay.
Seriously though, that's a good point: Con artists would have little need to operate within Federation territory, where all needs would already be provided for. So they would mainly be out in the uncharted territories. Which we rarely see! There is a Federation Security Agency (the guy in the bar in ST III) and also civilian police (the cop on the hoverbike in ST09). So Starfleet doesn't do absolutely everything.
Con men/women would have been more common in the AQ before the UFP was founded and in the 23rd century while the UFP was expanding and what would have become UFP space but isn't yet, and would have only begun to be 'regulated' when it did. The amount of scams would have likely dropped in the 24th century to smattering few occurrences (enough to make them something that USED to happen on a more frequent basis, but doesn't as much these days). The scams would probably be occurring at less frequent pace in the inner section of the Federation, and maybe a tad more near its borders where SF activity isn't too huge. Say for example the UFP/Romulan Neutral Zone... the Romulans may be more 'vigilant' in having more ships near the NZ on their side, however the UFP doesn't (probably as to not necessarily 'upset' the Romulans or needlesly appear as aggressive - we've seen how paranoid and trigger happy Romulans can get) apart from maybe a few patrol ships spread out - so SF activity would be lower in those regions. But we have seen some con artists in the 24th century too.
It's also worth noting that from several things said and presented in TNG and DS9 there's humans and whole human colonies that exist outside of the Federation for various (often unrevealed) reasons. And they don't seem to live in a Post-Scarcity society. Picard's fake son remembers going hungry as a child, Ezri's family worries about wealth and worker's rights on a colony that is called New Sydney (so likely of human origin). Tasha's planet is jut the most obvious example, but there seem to exist multiple such places and individuals.
There'll always be assholes looking to take best possible advantage of their situation at the expense of others. But in TNG, humans have "evolved" past all that. Halfway to Salamanders!
I mean TNG did have Shelby for example, who did use a few tricks in an attempt to get Riker's position whether he wanted to give it up or not. What Star Trek seems to propose (at least once Season 1-2 of TNG had passed) is that the removal of things like poverty through technology has stopped people existing in a struggle for survival against each other. So it leads to people being in competition for things they want (like being First Officer on the Flagship) rather than things they desperately need (food and shelter). And cultural shifts like most of humanity in the 24th century striving for self-improvement rather than money are always gonna happen, and with the miraculous technology seen in Star Trek cultural shifts would be inevitable.
Behavior is determined by environment. Change the environment and you change behavior. If the con artists grew up in an environment where they were distrustful of others and prompts them to 'earn a living' and resort to 'shady practices' in order to survive, then yeah, you'd get that kind of behavior. Sarcasm? Just because humans have moved past what is currently perceived as the 'norm' doesn't make it impossible or improbable. Its very much likely to occur in reality too if we got off our rear ends and used our science and technology to solve existing problems (which has been more than doable for decades). In fact, in reality, we don't have scarcity issues. What we do have are distinct lack in management of Earth's resources, using an outdated socio-economic system and 'forms of government' (filled with idiots who are not problem solvers) and a systems value disorder (which is a product of living in the said system). If you lived in an environment where you didn't have to worry about 'working for a living', 'paying bills' or earning money in general to survive, to go somewhere or DO anything, your outlook on things changes. You wouldn't be concerned (or obsessed) about acquiring material goods anymore because they would be accessible to you for use whenever you needed them. So at this point, you'd be concerned mostly with where would you like to travel to... study perhaps (fields of interest), how to possibly further improve the standard of living for everyone beyond what is already there and go actually DO stuff you find enjoyable and 'contribute' to society in that way (not through the notion of 'working a job'). In such a society, how one contributes is fundamentally redefined and has little or nothing to do with how we do things now. I know its a 'tough' concept for some to swallow, but that's a problem of living in the society we do because its filling people's heads with stupidity, detracts from the problems we have in the world, creating mindless 'diversions' all to keep the money game going (for the most part). And if you start delving into politics, you start realising just what a circus show it really is... filled with proverbial clowns who don't know jack about anything of actual relevance. Here's the thing... you don't need the 'miraculous technology of Trek' to do that in real life. All you need really is sufficiently advanced means to generate abundance for everyone... and we had those methods for a good part of the last 100 years now.... we area also already generating abundance, but we have massive inefficiency in regards to management and distribution of said resources (capitalism), Our methods of generating abundance are also heavily outdated (not in line with what could feasibly be done if we used state of the art methods) and as such require more land mass (even though we could easily reduce our footprint on Earth by 10 times at the very least).
Has anyone mentioned the drug dealing planet from TNG? So, basically we’ve all identified like…20 plots containing con artists of some variety.