On the night of his performance for Live at Halekulani’s Lewers Lounge, trumpeter Eddie Henderson, dressed in a dapper suit and penny loafers, is the epitome of cool. Though he’s a man of 75 years, Henderson has got the chops of someone far his junior. This makes sense, considering that he’s been honing his craft since he was 9 years old, when legendary singer and composer Louis Armstrong first taught him to make a sound on the trumpet while backstage at the Apollo Theater.

Interactions with such esteemed musicians as Armstrong, Billie Holiday, Duke Ellington, and Count Basie were hallmarks of young Eddie’s life. His mother was one of the dancers at Harlem’s original Cotton Club Revue, which featured the most prominent jazz musicians in its heyday in the 1920s and 1930s; his father sang with Billy Williams and The Charioteers, one of the most popular American gospel and harmony groups in the early 1940s. But it wasn’t until Henderson was 17, when he heard Miles Davis perform live, that he knew he wanted to play music for the rest of his life. “I’ve always loved music, but for me, that’s when the lights came on,” he says. “I heard that sound, and I was like, ‘I didn’t know you could do that with a horn.’”

Given his musical background, Henderson’s path toward music may have seemed fixed, but like any good scat tune, it meandered. When Henderson was just 9, his father passed away, and his mother later remarried a doctor, who moved the family to San Francisco when Henderson was 14. It was here where Henderson took up figure skating after his stepfather bought him a ticket to see the Ice Follies. He went on to become the first African American to compete in the U.S. Figure Skating Championships, having won the sectional Pacific and Midwestern titles. Henderson also continued to study trumpet at the San Francisco Conservatory of Music. His stepfather, however, wanted him to study medicine. So, following a three-year stint in the United States Air Force, Henderson completed undergraduate work at the University of California at Berkley, then received his M.D. at Howard University in 1968. “I remember one day [my stepfather] told me, ‘Being a doctor is the closest thing to being God,’” Henderson tells me. “But I was really only interested in music. He told me, ‘If you keep with just music, you’re going to be a bum on the waterfront.’ So I went out of my way to become a doctor to prove him wrong.”

Henderson has since retired from medicine and spends his days immersed in music in New York City, where he lives. He teaches at Juilliard School and Oberlin College and Conservatory, and spends about four months on the road performing with a group called The Cookers. After his time performing at Lewers Lounge in Hawai‘i, he will travel back to New York City for a short while before heading back out on The Cookers’ 2016 European tour.

For now, Henderson concentrates on his island performance—his second Lewers Lounge in two years. The deep sounds that come from his vintage Martin trumpet swell in the small lounge, where Henderson has begun a favorite of tune of his, “Cantaloupe Island,” composed by his hero and mentor Herbie Hancock. The prolific trumpeter is nearly halfway through his two-hour set, but it seems like he is just getting started.

Lewers Lounge, named after Robert Lewers who opened the original Halekulani in 1907, has become an oasis for jazz fans and cocktail enthusiasts alike, featuring contemporary and classic cocktails, paired with delectable bites and live entertainment. Since its launch in 2013, the Live at Lewers series has featured performances by the likes of Tony Bennett, Diana Krall, Jack Jones, Tierney Sutton, Robert Cazimero, and other legends of jazz. For more information, call Dining Reservations at 808-923-2311.