The work itself attracts people of a certain character and calibur, and even though we only worked together for just 5 days in a single year, it was a joy to co-manage that group.
I built tremendous rapport and trust with the group over those years, and for many, I was not just a leader, but I was their leader. On quite a few occasions I asked for some pretty ridiculous things and even if they didn't have the whole picture, my people were happy to jump on it because they knew the end result would be worth it.
One thing I did for the group was to create an afterparty so we could get together one last time after our work was finally over. As part of my planning process one year, I headed to Fenway Park at 11:00PM on a Monday (the same time the actual afterparty would be), and spent a couple hours in zero degree Boston weather scouting locations near Fenway Park.
A lot of places were packed with people despite it not even being Baseball season, but the Flask and Cagon was the perfect size and it was so empty I thought they were closing. I spoke with the manager and mentioned that I had a group of 50 looking to get together in a month at this very date/time. She said she would be delighted to have us because it's normally a slow period, and we locked it in.
I was among the first to arrive at the afterparty, and the Flask and Cagon was empty as expected. The team started trickling in. One of my forward-thinking team members pulled me aside and said "hey, I just realized they're checking IDs and one of our people is under 21. Do you think they'll be allowed in?"
I checked with the bouncer who said "absolutely not."
It was a perfect oversight on my part.
Luckily, the team member in question was considerably smaller than I was, and it was freezing freaking Boston cold, so I developed an ingenious plan: I went outside, waited for our team member to appear, told them to hide in my gigantic winter coat while I was wearing it, and while someone distracted the bouncer we would sneak in like ninjas.
He immediately saw through my 200 IQ play, and made it clear that people under 21 were not allowed and they did not use special wristbands.
I vividly remember the look on my contraband team member's face, and they told me to not worry about it, and that they would just leave and it wouldn't be a problem. To which I immediately replied something like "oh no, don't worry, we're getting you into this bar."
Understanding the guard's situation, I politely asked him if there were any other bars or restaurants nearby that could accommodate 50 people. He said no, so I opened the doors wide and said
"Everyone close out your tabs and stop ordering things - we're finding a new location."
The bouncer immediately realized the situation I put him in, told me to hold on a second, and literally ran to the backroom. Three minutes later he had a sharpie, put an X on their hand, and profusely apologized.