Online Edition

Celebrating Dick Wingate ’70 HGS: A Legacy of Passion, Innovation, and Positive Disruption

Dick Wingate ’70 HGS, Hopkins’ 2025 Distinguished Alumnus, recalls the exact moment he first heard “I Want to Hold Your Hand” by The Beatles on the radio. He remembers precisely whose car he was in and the street he was riding on too.
 
“It had that kind of impact,” he reflected. “The Beatles changed the way we, as kids, looked at the world. That was the first glimmer of feeling like anything’s possible.”
 
This glimmer of possibility was a guiding light in Wingate’s life. As he explained to the Hopkins community in a school-wide Assembly on November 15, 2024, the cultural force of music fueled his passion for media, shaped his career in the music industry, and taught him that change is always a good thing. 
 
“I ultimately followed my passion into the music business,” Wingate said. “But I could have never imagined the technology revolution, and the resulting changes that were to come in my industry.” 
 
Anything’s Possible
Now a renowned music and tech trailblazer, Wingate returned to the Hill to accept the 2025 Distinguished Alumnus accolade and to inspire the community that nurtured his early passions into remarkable career milestones.
 
“Hopkins prepared me and gave me the ability to take the enormous knowledge that I learned, apply it to my personal interests, and then apply it to a career,” Wingate said. “Without the base of knowledge that I learned at Hopkins, I don’t know that I ever would have been able to do that.”  
 
Before establishing his expansive career at Columbia Records, Epic Records, PolyGram Records, Arista Records, BMG Music, Liquid Audio, and now DEV Advisors, Wingate was an academically dedicated Hopkins student. He fondly recalled his favorite teachers, History teacher Karl Crawford and Math teacher Ib Jorgensen, as two adults who nurtured his love for learning. “I looked forward to those classes more than any,” Wingate said. 
 
As a student, he served as a features editor at The Razor and was a teenager who loved pop culture, New Haven’s top 40 radio station WAVZ, and attending rock concerts—all early signs of his passion for music and media.
 
“I was fascinated with the magazines that would come into the house that my parents subscribed to,” Wingate said. “I gravitated toward wanting to see and hear the latest media—that was the tip of the spear for me.”
 
After graduating from Hopkins in the top five of his class, Wingate studied at Brown University. His decision to attend Brown was driven by the school's curriculum, which allowed him to design an independent study program. It was not until Wingate established his own media studies program, became a DJ, and then a music and program director at WBRU-FM (Brown’s renowned student radio station) that he began to see the possibility of a career in media.
 
“It just started to come together for me once I got to Brown and heard the station, as it wasn’t anything like a top 40 station,” Wingate said. “It was one of the very earliest progressive rock stations in the country. The signal covered all of Rhode Island and the record industry doted on us as a result.”
 
From Brown to the Big Leagues
After spending a year at an independent record label (while also moonlighting on WPLR on weekends), Wingate landed a job in 1976 at Columbia Records as the youngest product manager on staff. This move secured his place on the business side of the music industry. During his Assembly speech, Wingate shared a rundown of his experiences at major record companies such as Arista, Epic, PolyGram, and BMG Records in the late ’70s, ’80s, and ’90s. While recounting his storied career, Wingate presented a slideshow of photos featuring him smiling beside music icons like Peter Tosh of The Wailers, Bruce Springsteen, Elvis Costello, Aimee Mann, Annie Lennox, and Robert Cray. He executive-produced hits and marketed the careers of these musicians and many others.
 
Although he never identified as a musician himself, Wingate credits his ears for his accomplished career.
 
“It was about my ability to identify talent,” said Wingate. “In the parlance of the music industry,
I had great ears.”
 
Foreseeing and Welcoming Change
A testament to his knack for anticipating the next big thing, Wingate devoted himself in the second half of his career to “evangelize change,” as he described it. “I’ve learned from the many different twists and turns in my career and reinvented myself a handful of times,” he said.
 
Evangelizing change helped Wingate continue forward in his career with success. He foresaw the rise of digital downloads in the 1990s—personally negotiating the first licenses from major record companies to offer their vast libraries digitally—and foretold the consumption of music through mobile phones in the early 2000s, a prediction
he stated in an LA Times article four years before the invention of the iPhone. 
 
“What I’ve learned in the music industry is that the status quo will inevitably be disrupted,” Wingate said. “And change can be very difficult to accept, especially when the status quo is working.” 
 
After helping develop some of the earliest mobile streaming apps for music and media companies in the early to mid-2000s, including Warner Music, MTV, and ABC Television, Wingate now runs a digital entertainment consulting firm, DEV Advisors, where he leverages his reputable expertise in the entertainment industry.
 
“For the last 15 years, I’ve helped dozens of new companies, artists, and investors to navigate the ever-changing landscape of the music and tech businesses,” Wingate said. 
 
Inspiring the Next Generation
In his Assembly speech, Wingate urged students to step out of their comfort zones and follow the path that makes them happiest, just as he did. “The biggest lesson that I’ve learned is: don’t be afraid to disrupt yourself. Don’t be afraid to take on a new challenge and pivot when the time is right."
 
Reflecting on his opportunity to address the Hopkins community and on being named a Distinguished Alumnus, Wingate expressed his deep gratitude and excitement: “I was tremendously honored when I received the offer to come and to receive the accolade and to speak. It was really exciting and I spent a lot of time preparing for that and enjoyed every minute of it.”
 
After Wingate’s speech, he roamed around campus, reminiscing about buildings like Baldwin Hall and Hopkins House, where he used to attend classes. He hosted a Q&A session in the Calarco Library, answering questions about industry trends and working with music legends, and visited a concert band class, sharing anecdotes from his career. “It was great to get some questions from the students,” Wingate said.
 
Wingate will be returning to the Hill during Alumni Weekend 2025 to receive the Distinguished Alumni Award and celebrate his 55th reunion with his peers, which he looks forward to. “I feel very blessed to have been at Hopkins all six years and to come back to celebrate.”

Watch Dick Wingate's Assembly Address from November 2024

Back
    • Voted #1
      Best Day School
      in CT, 2024

Hopkins is a private middle school and high school for grades 7-12. Located on a campus overlooking New Haven, CT, the School takes pride in its intellectually curious students as well as its dedicated faculty and staff.