Fairly pleasant, TBH.

I worked for a summer camp specifically for kids from some particularly dicey neighborhoods. Every so often I had to go set up shop in those neighborhoods to meet with parents and whatnot. Some guys in a local gang came to talk to me, learned I was there to offer something helpful to their kids, and from then out made sure I and my car were safe whenever I had to be in the area.

Nice guys, at least in the capacity I knew them.

I grew up in a town where it was general knowledge that retired Italian mobsters retired to.

They made sure that town was clean, safe, and with very little crime. Chased out encroaching gangs and were generally an overall positive for the community.

Since they stopped retiring there a few years ago, the town has gone to shit.

I went on a ‘Business Enterprise’ programme back in the UK in the very early ‘90s. Basically it was how to run a business 101. Six sessions on different things: accounting, HR, etc. etc.

One of the other guys on the course turned out to be the son of the biggest coke dealer in the city.

He was a nice kid. By the end of the course a bunch of us had bonded and someone invited us all to a house party.

The son of the coke dealer turned up with a briefcase literally full of cocaine. That was a fucking awesome party, let me tell you.

Very pleasant for me, my girlfriend in the late 90s and early 2000s was a mildly upmarket dealer, and I got work through her contacts which was usually safe. I ended up doing a lot of work through her dealer, who was the big fish in a town of about 300K people.

I got nice presents, got paid to chaperone his daughter and her friends for a week (free holiday!), got better work contacts for myself, very cheap electrical goods, free drugs, and had a favour I never got around to calling in.

I did spend a day digging up his garden looking for a nine bar of resin that he’d buried while high, which was hard work (we didn’t find it), and there was a time I was interviewed by police while I was hiding enough speed in my house that it’s sale could have bought said house, but it was otherwise just an informal business relationship with occasional blowjobs.

10/10 would do again.

I was driving on I-70 and saw a member of an MC execute someone.

One of my dad’s friends is in a local chapter of the same MC.

When my girlfriend’s dad was a kid he was once paid very good money to help unload crates off a boat and not ask questions

Also, and even less directly relevant to my life, I live a couple blocks away from a very famous dead gangster’s old hideout. One of the members of the gang, who lived down the street from me, went on to have a fairly iconic role in a classic mob movie

Having been a young white dude in the US, ive had all of the various christofascist or conservative terrorism organizations make a pass at me at one point or another.

Turning Point USA was recruiting from my school when I was a senior (right when it was starting up), a couple of the kids at my school were fairly well known for being in the KKK, and they tried to get basically every white kid at the school to come to their events. My college was a fairly small STEM college, so unless the FBI or the CIA count as organized crime, we didnt have a lot. After college the job market was still awful from Bush’s recession, I ended up with a job in a small town where the KKK, the Proud Boys, and the Republican Party held a weekly rally at the towns main intersection and liked to block traffic and generally be a nuisance…but the police chief liked to show up to the rallies (all 3), so you just learned to avoid certain areas on certain days.

I knew someone who lived in the same block as a well known motorcycle appreciation society. It was an incredibly clean and safe area. And the local dive bar was fun without a hint of shadiness or trouble. They did not shit where they ate.

Alright, I’ll bite. I got a favor from the mafia once. I had bought a motorcycle and the seller gave me an unsigned title, un-notarized. There was a Curio shop on our street - these ancient men ran it, but never sold a Curio, they did sell cigarettes and ran card games in the back of the shop. I told one what happened and he says "ah, don’t worry baby, Sam is a notary! SAM! This young lady needs something notarized. " So they signed the guys name and notarized it.
“What do I owe you?” “Nothing, honey, we do this as a favor for you, yes?”

I’m sure they are long dead now, and the curio shop some hipster bar or something . In their heyday they ran numbers and took protection money but had settled down, but it was funny, their job was sort of - if they could do it for you, and you could pay for it in some way, they would. So of course Sam was their crooked notary. And technically I owe the Mafia a small favor still.

When I was in the military we sometimes had to work with the US. CIA, navy, that sort of stuff. When it comes to crime, they are very organized. Especially war crimes are their specialty.

Once in Somalia a US sailing yacht was captured by pirates. A US destroyer intercepted and opened fire without warning. The yacht was completely perforated, covered in blood. The US crew, of which they knew they were alive, well and on board, and the Somali pirates were splashed open by .50 cal fire. And because they killed the US crew on the boat, they bombed a village as retaliation, claiming they were pirates while there was clear evidence there were only fishermen.

This is just an example of the many war crimes I’ve seen them do.

I used to work in a prison (I was a civilian kitchen supervisor, not a guard), and I encountered a lot of gang members from a variety of gangs. Kitchen jobs are highly sought after by inmates, because not only are they among the highest paying jobs an inmate can get, but the job also comes with essentially unlimited food. Normal inmates walking down the chow line would get 2 pieces on fried chicken day, but some kitchen workers would down a dozen or more. I say that to say: The gang members I worked with were on their best behavior so they didn’t risk losing their sweet gig. All feuds were on pause in the kitchen. Gang members who would otherwise be at each other’s throats were laughing and joking with each other, playing Spades during breaks, and eating at the same table. They all treated me with respect, and I didn’t have any issues.

The ones who didn’t work with me, genpop inmates, well sometimes things got very violent. I saw more stabbings/slashings than I can count on both hands, and I didn’t even work there very long.

Never worked for the government so idk.

A friend from primary school and his dad were in a biker gang. I was pretty close for a while, and saw some shit.

Studied abroad, made some friends. One asked me to ride along to his work. His work wasn’t ahhh, ‘above board’ and he had pissed off his boss, so he took me along as insurance that he wouldn’t be treated badly as their govt would be very pissed to have a foreigner disappear as well. Holy smokes, that was an intensive language immersion experience.

I worked near a clubhouse which used to be a lot more publicly active, in a trade that used to skew a lot more “rough”.

I heard that they trafficked women and that they would come to the job site to “work”. There were people with serious drug problems who could not be let go because of their affiliation. This last one I find the hardest to believe for some reason but apparently people were pressured into buying t shirts? Like with the clubs name and logo. Seems strange.