Prepping to Make a Difference

Jessica Alcantara reached seemingly unattainable educational heights through her impressive work ethic as well as the guidance of Manhattan-based nonprofit Prep for Prep. The organization places New York City’s academically gifted African-American, Latino and Asian-American students in selective day and boarding schools and mentors them on their pedagogical paths.

A student at The Mott Hall School in Harlem when she connected with Prep for Prep, the program placed Alcantara at Phillips Academy in Andover, Massachusetts, for high school. That was the Washington Heights native’s first time out of New York and she embraced the experience. “It was a nice change, but I liked both. I liked coming home for breaks and I liked going back,” she said.

That was just the beginning of her journey towards lifelong learning. She attended Dartmouth, then received a master’s at Fordham, and is currently earning a law degree at Columbia. When she graduates this spring, she will be relocating to Washington, D.C., where she will work with Advancement Project, a civil rights organization rooted in implementing policy change. Alcantara, who won the prestigious Skadden Fellowship awarded to graduating law students who will use their degrees in pursuit of public interest, will focus on black and Latino communities facing school closures.

What was your experience like growing up in Washington Heights?I enjoyed my time growing up there. Looking back, it’s hard to describe because I don’t know another way of growing up. I loved getting a quarter and buying an ice cream from the ladies who would park themselves outside of school. And going to the bodega before class starts or meeting up with friends and getting Chinese food. Things that are very uniquely a New York young person’s experience. I loved that aspect of it, that there are always things to do. We could just hang out outside on the stoop or go to a park.

When did you first connect with Prep for Prep? The public school system is different now in New York, but back then, when I was going through in the 90s, it was pre-charter schools. I was District 6 because I’m from the Heights at a magnet school for gifted and talented students called The Mott Hall School … Mott Hall had been sending kids to Prep; they had a history. So in fifth grade, they handed out Prep applications. I remember everyone in line and getting an application. And I remember not applying because I didn’t want to not graduate. Because I had left elementary school after third grade, I didn’t get to graduate in fifth grade. [Prep for Prep places fifth- and-sixth-graders in day schools.] These are the thoughts of a 10-year-old. Prep for Prep also had another version called PREP 9 [their boarding school program]. And that’s what I ended up doing. Two years later, in seventh grade, is when I applied to PREP 9.

You left New York to attend Phillips Academy. What was that transition like? It was a big change for many reasons. I don’t know how familiar you are with Washington Heights, but it’s predominately Dominican. If not Dominican, definitely Spanish speaking. Maybe it’s different now, but in the 90s, you could live in Washington Heights and never speak English. So the biggest change was probably, culturally, language wise, going to a suburban small town. Andover has that one main street where all the businesses are on, and that’s it. The rest is houses. But Andover was pretty diverse. I want to say it was one-third students of color when I was there. I think that’s around what it was. And they had a lot of international students.

Who were your mentors throughout high school?Prep had a mentorship component, so while we were still in the city, we were in advising groups led by older Prep alum. And then, while you’re at boarding school, Prep assigns you a placement counselor and every semester they come up and visit all of us there at Andover. We each meet with them individually; they buy us dinner one night. We still had the Prep support system as well as Andover’s own mentors and teachers.

You went back to teach at Prep. What subject did you instruct on?I taught there the summer before I started law school. I didn’t teach in Prep 9, the program I was in, I taught in Prep for Prep, the fifth-grade program. I taught a class called Invictus which was created by the founder of Prep, Gary Simons. It’s a class meant to help students think about how to be successful in school, work and life.

How did you choose Dartmouth for college? What did you study and what were your extracurricular activities there?I loved my time at Andover. I loved everything about it. And I wanted that again, essentially, for my college experience. I double-majored in geography and Latin American and Latino studies. I didn’t do much besides working. I had two jobs and worked about 20 hours a week. I worked in the school convenience store and I also interned at the medical school like an office assistant. Towards the end of college, I helped found a Dominican student group on campus.

After college, you joined the Peace Corps as a youth development facilitator in Azerbaijan. What did your job entail? It’s the type of development and extracurricular activities that they do in a Boys & Girls Club here. I did a lot of English conversation clubs. We did an arts camp in our town over the summers.

Now you’re in law school at Columbia. Did you always want to study law?No, but I always knew I wanted to go to graduate school because I enjoy learning. While I was in the Peace Corps, one of the counterparts I worked with was an awesome female lawyer. I saw all the power that she had and thought, “Maybe this is a path to implement change.”

You’re graduating this year and got a fellowship to work in D.C.The organization I’ll be working with is Advancement Project, where I interned last summer. And they have a partnership with the Journey for Justice Alliance, which is a national collation of grassroots organizations that are doing work on school closures. So with them, we’ll be deciding where, geographically, I’ll be focusing the work.

What are your future plans?The fellowship is two years, so I’ll be at Advancement Project for that time. And hopefully, if it’s possible, I would like to stay with Advancement Project because I love the organization.