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Henry Cole - I Made My Own Path

Nate Smith September 20, 2025

Henry Cole and I were almost classmates in music school. I missed him by one year.

What I did not realize at the time was that at the time I saw him performing in the concert hall with the Afro Cuban Big Band, Henry was in the middle of “some sh#t.” He had just gone home to San Juan, after quitting Berklee, before meeting John Riley, and becoming convinced that New York would be a better environment.

Acquainted with Miguel Zenon, Henry became the go-to sub when previous guest Antonio Sanchez was on tour with Pat Metheny, and eventually the drummer in the band. Cole admits he didn’t consider himself as good as Sanchez at the time, but says he made up for it in hard work - memorizing all of Zenon’s songs.

“This guy is not really great, but he knows the music already, sooo…” says Henry of Miguel’s apparent state-of-mind.

Before we go forward, I wanted to circle back to Berklee. Because - he quit Berklee? The Berklee of JP and Matt Garstka, and Zyck The Freak? Of (next week’s guest) Diego Ramirez, and (last week’s guest) Roni? The same Berklee with the “Snarky Puppy Ensemble” or the “Indian Ensemble”?

Berklee in the late ‘90s was, by Henry’s description, a very different place. In one anecdote, Cole recounts being shown a “clave” beat by a teacher with no background in Afro-Latin music, and preferring to do it the “authentic way” - the way he grew up doing it - and as a result receiving a number grade that barred him from playing with any of the “higher level” musicians. So yea, I can see why he’d want to save his money.

Fast forward to the 20-teens, and Henry is living in New York, “rage caving”. Aware of the chasm of ability he needed to make up, he describes an ascetic practice routine, starting in the early morning, breaking only for lunch, and going till early evening.

At that time, he was touring steadily with Miguel, and starting to play with friend of the channel Ben Wendel, as well as our mutual classmates Fabian Alazan and Linda Oh.

Then, in 2019, everything changed. A fire destroyed his New York apartment. Having lost everything, Henry returned to San Juan once again to pick up the pieces. It’s there that he currently resides. But he seized the opportunity to make his mark on the local scene and started his own bands, and recorded his own albums.

Henry also isn’t a stranger to New York these days. The week I’m writing this, he was at the Vanguard again.

Hope you enjoy this fascinating life story.

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