Hail to the Chief

Growing up, nobody told Gregory Haile about college. Now, as president of Broward College, he wants to tell everyone.

This summer, Gregory Haile takes the helm of Broward College. Here, he’s photographed at the handball courts at Hollywood Beach, a place that provides him an opportunity to de-stress.

By Ryan Pfeffer
Portrait by Eduardo Schneider

“I had a bullet come through my living room window,” Gregory Haile says, loosening his tie with one long pull before popping it over his head and tossing it aside. He is sitting at a slightly sticky wooden table inside a mostly empty Italian restaurant along the Hollywood Beach boardwalk. It’s hot and the air conditioning has apparently taken the day off. But Haile, dressed in a suit minus the tie, is all poise and concentration. “I lost friends growing up. Across the street from my house, they were selling drugs.”

We are only a few minutes into his narrative, but it’s clear that life has not always been easy for Haile, 40, who is currently describing what it was like to grow up in the ’80s in South Jamaica, Queens, where life was difficult for many. But good luck finding any trace of bitterness or resentment in his voice. Go ahead and spend an hour searching every square millimeter of his face for the slightest involuntary leak of anything resembling cynicism. You will come up empty. Trust us, we’ve tried.

What you’ll get instead from the man selected to become the next president of Broward College is an otherworldly amount of charisma and a passion for education that makes no attempt to hide itself. Starting on July 1, Haile will be responsible for the second-largest institution of the Florida College System’s 28 colleges, taking over for J. David Armstrong Jr., who held the position since 2007 and who leaves big shoes to fill. Under Armstrong’s tenure, Broward College expanded its services considerably, launching four-year bachelor’s degrees and finding itself as a finalist for The Aspen Institute’s Aspen Prize for Community College Excellence. Haile, most recently the general counsel and vice president for public policy and government affairs for Broward College, looks to build on Armstrong’s successes as he prepares to oversee a diverse enrollment of over 62,000 with a graduating class that, last year, included students ranging in age from 16 to 79. Haile was unanimously picked by the college’s board of trustees in May, and he can’t wait to get going.

All this from a kid who never gave higher education much thought for much of his life. No one in his family had been to college. It was not a common topic of conversation, especially once he got to the notoriously rough Springfield Gardens High School (which has since closed due to poor performance). “It was essentially the worst school in the city,” Haile says. “It was actually one of the first high schools in New York to be piloted with metal detectors.”

Naturally, college was less of a priority than survival. And even that was tough. The reason Haile has chosen this meeting spot in Hollywood Beach is not for the pizza but for the handball courts next door. Growing up, he played often. It kept him out of trouble and helped him blow off steam. But one day on the court things went bad. “Before I knew it, there were about 12 guys behind me,” Haile says. He was beaten terribly. It took “about 60 stitches” to close his forehead, which still bears the scars today.

Sitting on the gurney in the ambulance, he remembers looking to his mother and asking her why they had to live in their neighborhood. “I always think about how inappropriate it probably was for me to ask my mother that at that time,” he says. “But, I asked anyway.”

Haile wanted out—and who could blame him? When he finally started looking at colleges, he had no desired major or dream school. “I had no interest other than going as far as I could possibly go.” His 2.7 GPA was still enough to put him in the top 25 percent of his class and get him into Arizona State University.

In his role as Broward College’s president, Haile will oversee the second-largest institution in the Florida College System.

Things have looked up for Haile since then— but it’s never been easy. As a first-generation college student, he did not arrive on campus with the tools many take for granted. For example, he had no idea how to study. He remembers hearing a vague theory about comprehension being at its peak right before you sleep. “I said, ‘What if I study for an hour before bed and then I sleep for an hour and then I wake up and study for another hour, and do the same thing throughout the night?’ I did that for an entire semester,” Haile says. He does not, by the way, recommend that. Still, by his second year, he found success through sheer will. “I got my first 4.0 and never got anything less than an A after that,” he says. After ASU it was on to Columbia University for law school. He also recently taught classes at Harvard University.

Haile clearly figured out how to navigate the system of higher education, but he knows that is often not how it goes for students in similar situations. “A school like Broward College should be focused on penetrating communities that, frankly, don’t know we exist,” Haile says. “I learned about college for the first time in sixth grade. I don’t think that should ever happen.” And that’s one of his big goals as the president of Broward College: to ensure that the community, from elementary school students to high school seniors to single parents, not only knows what educational opportunities await at the college but also know how to take advantage of them. The unemployment rate in Broward County hovers around 3.5 percent, and Haile sees no reason why Broward College can’t help lower that number.

He thinks his experience gives him a unique opportunity to connect with the student population he will soon lead, and it’s hard to argue that point. Many Broward College students are first-generation college students. So was he. Many Broward College students require remedial education. So did he. Many Broward College students are Pell Grant recipients. So was he.

Haile is a father now. He and his wife, Chae, who he met during his freshman year at Arizona State University, have two daughters, 6 and 3 years old. “One of the things I have always promised them is that they would never remember the first time they learned about college,” Haile says. “They’ve been on college campuses since they were born. That’s part of the difference. It is a lot easier to persuade them now than it is at 16 or 17 years old. That is not a short-term strategy—that’s a long-term play. We want to build a different kind of culture around education.”

This article originally appeared in the Summer 2018 Issue.