The story begins with his 15th great-grandfather, a man named Andrés de Llerena.

In records, Andrés is described as a Guanche, the Spanish word for a Native Islander, and it seems that he suffered a great deal for that very reason.

Whoa.

"He, Andrés, specifically states that because they are Guanches, Fernández de Lugo hates them and drives them from their land, and from said island of Tenerife wherever he wants."

Your 15th great-grandfather, Andrés, wasn't Spanish.

He was a member of the indigenous people whom Spain conquered when they colonized that island.

That's unbelievable.

How about that?

What's it like to learn that?

It's deep.

I can't imagine, you know?

It's like you, it's people just driving you out.

The Spanish conquest of Tenerife was brutal.

Significant numbers of indigenous people died in battle or from disease, but Anthony's ancestor faced a different ordeal.

A record from the year 1506 places Andrés on the estate of a conquistador, and makes clear that he was not there by choice.

"You, Fernando de Llerena, have a Guanche slave named Andrés."

Did it ever occur to you that you descend from someone who had been enslaved?

Explains why I got that fight in me, yo.

Yeah.

But... You know, I always had thoughts like what if, you know?

You never know when you're Puerto Rican or you come from one of the islands, or your family comes from one of the islands, you just don't know.

Right, no, you don't know.

It's a mixed bag.

You don't know who's from where or from what happened, so you know, I've definitely wondered like, I mean.

Well Anthony, we do not know exactly the circumstances under which Andrés became enslaved or how long he lived in bondage, but we believe it was for at least 10 years, considering the conquest of Tenerife ended in 1496.

That's a long time to be a slave, man.

This story was about to take an incredible turn.

Records show that in 1506, Andrés persuaded his enslaver to allow him to find another human being to serve as his permanent replacement, thereby allowing him to go free.

He had to find a substitute slave to take his place.

How do you convince somebody to do that?

"Yo, my man, can you just like take my place with this family?

I'm just trying to get this freedom real quick.

I promise like when I get my freedom, Imma try and come back and get you, or something."

Like what kind of, how you make that deal?

Well, you said your father was a fast talker.

That's what I was literally thinking, my dad.

My dad would've talked his way into freedom, 100%.

I remember those cans of Raid.

My dad would've been the only slave like, "Yo, trying to, yo I promise Imma get this freedom.

You want this freedom too?

Come on with me."

Andrés's deal was unusual, but it wasn't unprecedented.

By this time, a trade system was already in place bringing enslaved Africans to the Canary Islands, and that's likely how Andrés obtained his replacement, possibly with financial assistance from his extended family.

Even so, it's hard to believe that anyone could have predicted what Andrés would do with his freedom.

After marrying and starting a family, he joined a Spanish military expedition against North Africa and was never seen again.

We believe he died fighting for Spain.

What do you make of this?

I don't know.

I can only imagine that he was probably like, "Yo, this is probably the easiest way for me to have a better life."

Yeah.

"So, you know, F it, I'm out."

Yeah.

"I'm gonna side with these guys 'cause they got it better, and if I got a, if I see a window, then..." You know?

The only way up, the Spanish weren't going anywhere.

Right.

I mean, they're still there, - in effect.

- Yeah.

So the only way was to become part of the system, and that's what he did.

Right.

It's that every man for himself kind of thing, you know what I'm saying?

Like I can't imagine that he was really thinking - about morals, - No.

in that moment.

No, no, but what a story.

It's unbelievable, man.