Over the course of 30 years....yea, several, but I spent most my life in Indiana with a CCW law dating back to 1934 so it is no big deal, even to cops.
My buddy Tony drove sprint cars (race cars) and I was dating the daughter (Linda) of the track promoter (Ed) in Lawrenceburg IN, I had just turned 21 and got my permit, I was in the Marine Corps officer selection program and planning on being a pilot. One night I had worn a T shirt with a crazy cartoon character of a jet pilot during the race, but had changed into more presentable clothes because we ate dinner with the promoter’s family after the race. Tony and I were in the concession office while Ed and his wife counted out the payoff money and Linda was cleaning up the concession stand and there were 6 local cops Ed paid for security. Linda suddenly jerks open my cover jacket and says “I want to see this T shirt everyone is talking about.” Well there is my S&W 19 round butt in a cross draw holster for all the world to see, Linda’s eyes get big as saucers and she looks over at the cops, expecting me to get shot or hauled off in irons. This is how the exchange went…
Cop 1 “is that a round butt 19?”
Me “Yes”
Cop 1 “I bought one for off duty but I don’t like it, the grip is too small and I can’t get a good hold on it.
Me "have you tried a Tayler's T Grip adapter?"
Cop1 "A what?"
Me “Here let me show you” I upholster, empty it and hand it over to the cop and tell him he can dry fire it to get the feel
Cop1 dry firing my RB19 “Hey, this is nice, what did you say this is called?"
Me “Tayler’s T Grip adapter, here I’ll write it down, any gun shop should be able to order it for you.”
Cop 2 to Tony “You carrying too?”
Tony “Just this” as he pulls a stainless chief’s special from an ankle holster, empties it and gives it to Cop2
Me to cop 1 “Is that a new S&W 66?”
Cop1 “Yea, check this out.” He upholsters, empties it and hands it to me.
Any way it turns into a general “I’ll show you mine if you show me yours” session, meanwhile Ed and the family are standing there shell shocked.
A couple weeks later Ed had trouble with a stock car team and threw them out, and the cops had left early when Ed discovered they were laying for him and his family just outside the track. He sent his son to make sure Tony and I were still there, asked me to get his kids out safely…but that is another story.
Another time we were on our way home from this same track and stopped to help a couple high school girls on their way home from a school dance had blown a heater hose in an old Ford Falcon. This was on a very deserted stretch of highway with a reputation for danger. Since we had all the tools for the race car it was pretty easy to rig up a bypass. As I was finishing up a state cop headed the other way stopped to see what was going on and held his flashlight in the engine compartment as I worked. Well we wore waist leanth team jackets and I had switched to a 4" S&W 66 carried OWB just behind the hip and the jacket had fallen behind the grip. As we watched to make sure the bypass would hold the state cop shined his light on my gun and said "Oh, by the way, you do have a permit for that don't you?" I said I did and started to reach for my wallet, he said "That's OK, just asking, your buddy carrying too?" I said he was and reached for my wallet again and he says "No problem, I just thought you were pretty stupid for stopping on this stretch of highway late at night, but I see you have things covered so I'll be on my way." Gets in his car and heads off, we tell the girls we'll follow them home to make sure they make it OK and off we went.
Or do want to hear the one where I was driving the little truck of a buddy that had a leather booth at the state fair. Every other night we alternated taking the deposit back to our home town 50 miles away, and I had spent the night with my girlfriend and was running late getting back to the fair the next morning and was speeding. Well I got stopped by a state cop and while looking for the registration I explained it wasn't my truck, I opened the center console and there was a chief's special laying on top of a baggie of grass

:whacko: