05 Jun NiteCap Journal: Why NiteCap Live in the VI?

When the young waiter came up to me at dinner I wasn’t in a particularly good mood.

It was one of those days spent navigating the mental fog we’ve all found ourselves in post Irmaria and now COVID – the melancholy blues that echo cries of loved ones gone too soon.

Needless to say, I chose a discreet corner of the restaurant, a secret gem nestled on the sand on one of my favorite beaches to sort out my mind’s ramblings.

Sitting there watching the tide roll out I beamed a broad smile in anticipation of what I came for.

The sunset began to creep in beneath my sunglasses, so I took a deep breath and exhaled.

Only on St. Thomas.

“I knew it was you!” the waiter said emphatically, now standing over me at my table.

Startled, I arose out of my daydream. By now, I should’ve been accustomed to being intruded upon. Imagine standing 6’8” in a world where few ever stop to ponder this:

I probably may be the millionth person to ask this man if he plays basketball and it just might irritate him.

I waited.

“You’re Peter Bailey,” he told me, quite adamant about it. “I attended one of your NiteCap Live shows when I was in high school.”

I lowered my shades then sat upright.

“That show really helped me. It really opened my mind to a lot of things,” he continued.

I peered into him, oblivious to the other patrons, primarily tourists who were now all enthralled by our conversation.

“Nancy, I told you he was an NBA player,” whispered one portly fellow patron wearing an I love St. Thomas T-shirt. “Dad, can I go ask him for a picture?” asked his eager son. “No, Paul that would be rude,” his mother chimed back.

The waiter looked around.

“Oh, I got bigger dreams than this Mr. Bailey,” he affirmed to me. “I’m saving up to be an entrepreneur. Just like you.”

I nodded.

By now, I had forgotten about the missed sunset. This exchange was more than I had wished for and it compelled a moment of reckoning, one that reminded me of why I brought NiteCap home to local high school students.

As I’ve shared in this journal before, I always felt geographically isolated from my dreams growing up in the Virgin Islands so I’ve long desired to create a bridge to connect the next generation to theirs in a forum on their terms. Enter NiteCap Live in the VI. It’s where I was first introduced to Indira Labone and her resounding talent, now featured in The Unbreakable Virgin Islanders. During that memorable NiteCap Live featuring Julius Jackson, I decided to invite both public and private school students, because our society has been divided along economic lines for far too long. As irony would have it, some of the All-Saints Cathedral students in attendance asked me to give their graduation commencement speech leading me to stay in the territory.

In a tortured twist of fate, myself and Julius would find ourselves picking up the pieces of what Irmaria left some four months later.

Since that fateful restaurant encounter, I’ve had many former students and teachers share their NiteCap Live memories and how it built a bridge to realizing their own potential so I’m dedicating this Sunday’s journal to this defining chapter in our journey from our very first NiteCap Live in the VI featuring actress Bresha Webb. Take a look below:

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