An unlikely mentor helped Henry Flores ’01 regain not only his academic standing, but also the confidence to take his seat at any table.

In October 2023, Flores shared his story as part of the “Purpose and Place: Voices of Middlebury” event during the campus launch of For Every Future: The Campaign for Middlebury. 

Watch Flores’s talk above or read the transcript below.

Transcript

So I first arrived at Middlebury in September of 1997. I was decked out in my Woodbury Common Outlet finds. I had a fresh fade from my barber, Felix.

And I was confident that Middlebury had never seen a student like me before. You know, Dominican kid from the projects of Spanish Harlem, raised by a single mother, first in my family to go to college, National Merit Scholar, Presidential Scholar, et cetera, et cetera. I was pretty confident when I arrived on campus. So confident that, you know, having come from an all-boys Catholic school being repressed, I spent the whole few weeks partying it up at social houses, trying to meet girls.

That was until I got my first graded paper back from Miguel Fernández and it looked like he killed a leprechaun on it. It was like all green ink and it basically said, Henry, you can do better than this.

So from then on, the only girls I was hanging out with were Jane Austen and Gertrude Stein at my new social house, Starr Library.

And one Friday night, as I was there still studying, my friends, each one of them coming patting me on the back saying, “Hey, let’s go party.” I’m like, “I can’t, can’t tonight, can’t tonight.”

It dawned on me that, you know, my friends can afford to do this. They’ve gone to schools like Choate, Andover, Brearley. They’ve already done four years of college in high school.

And, you know, by the end of the semester, my swagger was gone.

You know, I had an afro. There was no barber on campus. I gained 15 pounds due to my friends Ben and Jerry. And I was on academic probation.

You know, I was a straight-A student in high school. And now academic probation, like what in the world happened?

And I was at a crossroads.

I was stressed, you know, I thought I’d bit off more than I could chew, and I was thinking of transferring.

J-term comes around and while my friends are taking classics, like Physics for Poets, and hitting the Snowbowl, I was taking Caribbean Anthropology and History with Professor Arnold Raymond Highfield, a visiting lecturer from the U.S. Virgin Islands in St. Croix. Now, that classroom looked a lot like my classroom in the South Bronx. Every Black, Latino, and woke white student on campus was in that class, 8:30 on the dot hits, and in walks Professor Highfield.

I didn’t know what I was expecting.

I was expecting a Black militant professor with a huge afro, with a comb—with a pick—and a daishiki. And what I see is this elderly white man with piercing blue eyes, a red beret, and a twang that I can’t quite place.

And he had a kind of limp to him, which I kind of recognized from my neighborhood. We call it “hood swag” in Spanish Harlem. Like he had that, he had that thug walk, I thought.

And I thought, “There’s more than meets the eye to this professor.”

So for the next couple of weeks, he taught us about colonial racism, racism in the colonies and in the U.S., and how people often judge you by your skin color rather than you know, your culture, your language, or your faith.

And it made sense to me why I always felt so isolated at Middlebury after hearing that. ’Cause I felt that way too.

Plus I felt isolated academically as well. So I remember going up to talk to Professor Highfield after class one day and I remember him saying, “Well, Henry, this is gonna take a lot more than five minutes, so why don’t you come to my house for dinner tonight and we can chat then.” 

So I remember pulling up to his house and the door was wide open and he was sitting there in his study, grading papers. And before I can knock, he sensed my presence.

He’s like, “Henry, buenas noches, come on in, make yourself at home.”

I come inside. His wife, Shirley, this Black Cruzan woman, gives me a huge hug, and she tells me to sit down and wait for him. And as I’m sitting, I’m looking at the frames on his walls. There’s family pictures: four beautiful biracial children. And before I could get too comfortable, I hear him say, “Henry, come on inside, let’s talk about this.”

So I go into his office, I sit across from him, his piercing blue eyes there, he sat back, his legs crossed.

He’s like, “So tell me why you hate Middlebury and why you want to transfer.”

And I’m like, “Where do I start?” So I just unload on him. I’m like, “I don’t understand how you do it. I don’t feel home at home here at all. I feel like a complete outsider.

“You’re a white guy who teaches Black history to Cruzan kids in St. Croix. How do you fit in? How do you make it work? Aren’t you tired of being an outsider?”

And he just laughs and he says, “Wow, you really get right to it. I like that.” 

And he says, “Look, I was just rereading your essay, and we have a lot in common, actually. I grew up poor, but I grew up poor in Appalachia. I lost my father when I was young too, like you did. You suffer from chronic asthma. I suffered, I survived childhood polio. This is why I have this limp. And I too was the first in my family to go to college. And being the first is really hard.”

And he told me, “Middlebury is not a level playing field for students like us.”

He’s like, “I’m gonna make a proposition for you. It’s gonna be like an independent study of sorts. You come and sit with me two to three times a week and I will give you reading assignments.”

I’m like, “Great, more reading.”

He’s like, “I will assign you some reading that I think will help you catch up.

“I’ll give you some, you know, additional writing assignments to do. And before you turn in your actual papers for your classes, let me take a look at them and I’ll grade them for you, I’ll correct them for you and make some suggestions. But think about it. You know, you’re a smart kid, you just have to want it more than everybody else does.”

I didn’t think about it long. This was an opportunity that I needed. This was the lifeline I’d been praying for. So I immediately said yes.

And for the next year, he and I met two to three times a week. Sometimes at the Panda House in Marble Works, the Chinese restaurant—we went there so often the owners there thought I was their kid—or at their house in Chipman Park. 

And you know, Shirley and Arnold had become my surrogate family in Middlebury for four years.

Their home became my home. Every time I showed up, Arnold would always say, “Hey, come on in, make yourself at home.”

And what I learned through all the many lessons that he taught me and through everything that I was learning, was that he was teaching me how to be at home with myself.

How to have the confidence to walk into any room, to talk to any person and feel like I belong there.

Like that seat at that table was mine and nobody was gonna take it from me.

Arnold and I were friends for 23 years. I came up every year to visit him here at Middlebury or at their house in St. Croix. And he met my mom.

My mom would send them food all the time ’cause he loved Dominican food.

He met plenty of my girlfriends, some he liked, some he didn’t like. He met my wife and eventually my daughter.

On September 8, 2019, Arnold Raymond Highfield passed away. And for the first time since I was a freshman, I felt alone again.

I felt without a place in this world, without a home. That further compounded it with the pandemic.

My wife and I were in a two-bedroom apartment in New York City with a five-year-old. And we, like so many other families, were looking for a second home as an escape valve.

We picked one in Woodstock, New York.

And as I’m driving up there, the GPS chimes on and it says, “Make a right on Arnold Drive. Make a left on Raymond Road, and you’ll be home.” To this day. Arnold Raymond Highfield is still leading me home.

Thank you.