I did a few times when I was either desperate or wanted to take off the cocky college guy.
I use to shoot pool at the Bus Stop Bar on Union Street in San Francisco a bunch. They had 2 nice 8 foot bar tables and I always played for fun and laid down most of the time to get free drinks and very cheap action from time to time. Well one day I lost my job (down the street) and I knew the owner of this Italian place liked to bet with me was at the ol Bus stop doing his thing. I came in and asked if he wanted to play. He smiled his crooked smile and says "Sure 5 bucks a game.."
I told him, "NO... I want to play best out of 5 (like most nits say instead of race to X) 8 ball for $50. "Im in the mood to gamble and I know you like to bet it up so...."
He looked at me with a sharp glare for about a solid 5 to 7 second and then said, "Sure!! Why not?? Im a rich guy and Its lika the black jack eh??"
I only had $40 bucks in my pocket and I knew I had to win so I held nothing back and smoked him 3 straight with him getting 4 turns at best. Afterwards he looked at me with some pretty very heavy distain because I was playing on the lemon with him for months!!! He knew he was scammed and when I asked him to play again he put his cue on the rack and walked out without saying a word.
I never did go back there after that. For one I didn't work down the street anymore and for two It was his watering hole and I felt pretty bad about hustling him and didnt want to see him again. If I wasn't so desperate for money I would have never done it. Luigi was a pretty cool guy and always offered me a warm friendly game. I did forget to mention that he could play a little but he was nowhere near my top gear.
Pic of the place:
Last hustle I ever pulled was, again, On Union Street in San Francisco at the Mauna Loa bar next to my old work. lol
Went in one night after work to have a beer or two and heard a racket of noise coming from the pool table. The bartender knew how good I was and told me this guy is gambling with people and was pissing people off. I told her not to say anything about my skill set and if I win some ill tip her out a percentage. She smiled and let out a little giggle that got me amped up.
When he called my quarter he asked me to play for $20 bucks... I smiled and said.. "I usually play for $50 a game not $20.."
At first I thought for sure he wouldn't bite and then he said... "Well if you are willing to play for $50 why not make it a $100 a game??"
I was so excited I was jumping out of my skin because ive been watching this guy play for about an hour and he couldn't hold a candle to a B player!!
I then said "Standard Bar rules but the 8 ball doesnt have to go in clean ok?"
"Why not??" He asked..
"Well this table is filthy and the balls slide on some shots. Also its not exactly level in certain spots so the ball can drift at the end of your roll."
"Do you think that you should lose because of the table and its bad conditions??"
He answered, "No..."
"Well good then put your hundred on top of mine..."
He posts his hundred and he breaks dry. I play soft on him and let him make a few shots as he is high fiving his drinking buds and winks at the chicks in skirts. I just laugh on the inside as I cooly slides the last 3 balls of my set and pocket the 8 ball clean in the corner.
He smiled and said good game you wanna make it double or nothing?? Why not right??
I break and make a few solids and dog a 4 ball in the side and do this ---->

LOL
He steps up makes 2 great shots and looks good for the rack and then... Thump... Dunks whitey in the side off the bottom rail. I held in my smile and smoothly ran the rest of the rack to up my winnings to $300!!
Now he was a little hot but the games where very close and I was still no where near my speed. So to him I was playing good bar pool and not hustling him :lol:
He then offered to play me one more for $300 and it would be our last game of the night. I said sure no problem at all. I will let you try to get even and I have no problem with that.
He racks and I noticed the head ball was very loose in the front. I didnt demand a re-rack due to the situation I was in like gambling HUGE in a bar and playing a guy stuck 300 and going for it so I broke. BAM!!!!!! I smashed the second ball in and the 8 ball came flying out and went in the corner pocket and the cueball stopped on the rail next to the side!!! The place went NUTS!!! My friend that was with me had his jaw on the ground as I gave him a huge bear paw hug and shook him back and forth laughing!! My opponent handed me the $300 out of his grapefruit sized roll of cash and smiled.
"Nice shooting tex!! You got luck but you aint too bad either..."
I smiled and shook my head and said.. "Better to be lucky then good!!" Ive always wanted to say that to somebody :lol:
I bought him and his buddies a round on me and tip the bartender $200. She came around the bar, grabbed me and laid a big wet kiss on me and grabbed my ass.

:lol: She smiled at me and said to stop back by soon to see her. No diggity... No doubt..
Turned out the guy was a high end attorney that just loved to gamble and I was in the right place at the right time so $600 to him was no big deal so there wasn't any hard feelings or a sense of impending doom that can happen in bar room sessions. Would I do that nowadays?? HELL NO!!! The payoffs are too small to end up in the hospital or dead.
Here's a pic of the place:
I do miss laying low and putting on the show by being slick but I was younger and didnt know any better. It's like what others have said in this thread. I rather jump in the box with a world champion and try my best to smoke em. Testing myself against the best is where its at and I dont care if I lose. As long as I go down swinging he or she will remember me and my game and to me that's where its at
