James Kenneth Drennen

James Kenneth Drennen, 81, passed away on Tuesday, December 16, 2025, surrounded by his loving family. Jim was a man of strong contrasts—solitary yet adventurous, humble yet commanding, thoughtful yet stubborn. Standing 6’6” with a large frame and unmistakable presence, he could fill a room instantly. And yet, at heart, he was an introverted man who enjoyed his independence, lived by his "golden rules", and did things his own way. He enjoyed life and nature and was grateful for each day he was given. He cherished his family and friends, delighted in his precious land along the Pequea Creek, and was a proud bar owner—there is no rock like The Shamrock. In his younger years, he did drywall work and loved hunting and fishing with his buddies. He adored and participated in the Ocean City White Marlin Tournament for many years. He completely loved taking long road trips out west and frequent short trips to Atlantic City. He encouraged his family and friends to join whenever they could go along, sharing his favorite routes and spots with them like rare and valuable treasures. He was fascinated with reading the newspaper, especially the weather section and his favorite nature columnist, Ad A. Crable, III. He often said the three strangest things in life were love, death, and the weather—and he had strong opinions about all three (and everything in between). Jim had a deep appreciation for words, quotes, and phrases that carried meaning to him. One motto he loved—and frequently inculcated into his children—was, “All for one, and one for all.” It mattered deeply to him that his family stayed close, forgave freely, and helped one another. In recent months, he was especially fond of an Irish blessing he never quite quoted correctly but always meant sincerely. He'd say... “May the best day you ever have, be the worst you ever see.” Jim was known by all as The Music Man. He was our Shazam before it ever existed, always whistling a tune or singing a song—sometimes even into our voicemails. He often said there were three songs he wanted his children to know and remember: “Candida," “I Only Have Eyes for You,” and “Close to You.” He also held songs close to his heart for his ex-wife, friend, and close companion of 54 years, Eileen, including “Long As I Can See the Light” for their first dance together and, “Can We Still Be Friends” for after their divorce. Jim loved a good argument (just ask his best friend, Joey DeMora). People either loved him or hated him, and he was perfectly fine with that. Many of his choices were bold, unconventional, and often very funny. His size helped him get away with things most people couldn’t, which was sometimes shocking to witness. James brought five children into this world. In birth order, they are...James Jr., Kelly, Corina, Talia, and Brandy. Unfortunately, and to his regret, he was estranged from his first two born and never got to meet three of his grandchildren. He didn't know how to mend that brokenness, so he just held love for them in his heart. They mattered to him always, and he prayed for the best for each of them. He had four grandchildren in his life that were blessed to know his love. In birth order, they are... Thaddeus, Wyatt, Maeve, and Raeya who already greatly miss their beloved Buckaroo. He will be remembered as a man who lived fully, argued passionately, laughed often, and loved his family deeply—quiet in some ways, unmistakably bold in others, and always entirely himself. May he rest in peace within the good graces of our Heavenly Father. We love you Buckaroo, forever and a day.