Since I mentioned it...
A number of years back, I got a call from a singer I had been doing some work with. He wanted to know if I would be willing to come up with him and two other well-known singers to perform for the Jewish prisoners at the Otisville Federal Penitentiary upstate on the night before Shavuot. Although I was not convinced that it fell into the category of a "mitzvah gig", I volunteered to do it so long as he would drive me there and back. I figured that if nothing else, I'd get a good story out of it. As expected, I did.
When he showed up to pick me up that night, the mandatory sidekick all these guys travel with was along for the ride. I got into the car and "Sidekick" asks if I'm hungry. I ask what he has, assuming he'll offer chips, cookies, and the like. Instead, he asks if I'd like shnitzel or stuffed cabbage.
Turns out there are quite a few trays of shnitzel, stuffed cabbage, deli, etc. in the back. The guys than tell me that the real reason the concert was scheduled is so that we could smuggle the food into the prison. It turns out that the brother of one of the prisoners owned a restaurant and they'd set this event up as a way of getting the food into the prison for Shavuos. This guy wanted to "give kiddush" for all his friends. Apparently, you couldn't legitimately bring in that amount of food in, so it had to be smuggled in. I felt uncomfortable with the situation, but there wasn't much I could do at that point, so I just kept quiet.
The other two singers were driving up in another car and every now and again, "Sidekick" would check in with them via cell phone. (This will be relevant on the way back.)
When we got to the low-security prison, a Chassidish man in prison uniform comes out and motions to us to park behind the building. We park and get out of the car. One of the guards comes over and asks the singer why he parked in the back, instead of parking in one of the clearly marked visitor parking spaces in front. The singer tells him that one of the prisoners directed us to park there. The guard asked which one it was, and the singer replied, "oh, they all look the same." The guard first asked us to move the car, but since we'd already gotten out and begun unloading, he relented and let us leave the car there, even though it was out of sight of the guard booth.
We entered the prison, leaving the car doors unlocked, and set up for the show. After first davening mincha, we began the concert. I'd say there were about twenty people at the show. (There were more at Mincha.) Some of the Jewish inmates refused to attend because they were embarrassed and a few skipped the show for "religious reasons." It was a very strange gig.
Incidentally, the prison has a vending machine with "Meal Mart" deli sandwiches in it. And a Daf Yomi shiur.
It was interesting to speak to the prisoners. Some were clearly embarrased by what they'd done, but others were just as clearly not remorsefull at all. One guy proudly informed me what he'd done to get there. (It involved fraud with Govt. programs.)
Before we left, some of the prisoners came and snuck the food out of the car.
One of the most surreal moments of my life has to have been sitting in jail playing the song the prisoners requested, "Just One Shabbos" with its chorus of "Just one Shabbos and we'll all be free" as they all sang along.
Finally, to cap the night off...
On the way back, "Sidekick" was on the phone repeatedly with the singers in the other car and was laughing hysterically. Eventually, he told us that the other guys were, um, er, getting high and it wasn't on Torah. In other words, these guys (who had a reputation for uh, indulging) were stupid enough to bring the stuff into a Federal prison, potentially getting us all into trouble. Nice.
It was quite a night.
Note: Names have been omitted to protect the guilty.