Lena's paternal eighth great-grandfather was a man named Stephanus van Cortlandt.

Stephanus was born in 1643, in what was then the Dutch settlement of New Amsterdam, and is now part of New York City.

Holy moly.

Did you have any idea that your roots in the city go back to the 1600s?

Absolutely not.

I mean, I always felt like, okay, my parents came to New York in 1971, and then came me, and I knew that we'd had relatives who lived in upstate New York and maybe had homes in the city, but this is a pretty wild connection to the city.

Stephanus wasn't just any New Yorker, he was a successful merchant with a talent for politics.

When the British conquered New Amsterdam in 1664, he won their trust, held on to his business and ultimately became the first Mayor of New York who had actually been born in the city.

- He was the mayor?

- He was the mayor.

My eighth great-grandfather was the Mayor of New York?

He was the mayor, and not only was he the mayor, he served two terms as the mayor.

Wow.

First between 1677 and 1678, and then later from 1686 to 1688.

That is not something that I ever would've guessed at.

Stephanus had some positive effects on his hometown, and even helped to plan New York's first public wells.

But he also made a series of deals with the Lenape, a Native American tribe, obtaining access to thousands of acres of land in exchange for goods that were likely of little value, a revelation that saddened Lena, even though it didn't surprise her.

I always assumed that there would be plenty of things that my ancestors had been involved with that were things that I would find to be sort of morally and spiritually reprehensible, if we wanna use that word.

And we all have to reconcile ourselves to the fact that we have members of our family who may have thought that they were doing the right thing for their families and for the people in their, you know, he may have thought he was doing the right thing as a leader, but I think we understand now that that's not how we want people to lead.

And so we all have to find a way to both be interested in our history and embrace our history, and also really reckon with the parts of it that we would love to rectify.

Mm-hmm, parts that you find unsavory.

That's exactly right.

And I think it's important not to hide from those things or pretend that they're not there, but instead to examine them and think about how we can not do modern repetitions of ancient behavior like that.

There was another beat to this story, one that would render it even more unsavory.

In 1691, Stephanus wrote a letter to a fellow merchant, detailing some of his business plans and laying bare one source of his wealth.

"I have written to you before my departure for Long Island.

I am now going to Staten Island to rouse up the collection of the tax there.

I will supply myself in order to send up as much pork in the spring as you will order, if you can, let Rensselaer to provide the people with small beer.

He got a Negro boy from me, and thus it will be easy for him and me to settle with each other.

So you know what that means.

- Yeah.

- Most of us think of slavery as unfolding in Mississippi and Alabama.

But it was everywhere in the United States.

- Absolutely.

- And certainly in New York in the 17th century.

- Yeah.

- Did you ever assume that your ancestors would've owned slaves?

I think like many Americans, I naively hoped that because they had always been living sort of in Yankee territory, that it looked different.

But of course, that is a part of the lives of those people too, especially stretching this far back.

And it makes it impossible to kind of celebrate or be excited about any of these other, you know, great, he was the mayor, but... That's... To me, that's the stain on the record.