Gerald Caplan, Cuba Hollaway, Lloyd Rich, and John Rotole
September/October 2024
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In Memoriam is a complimentary service of the CBA honoring the lives and work of recently deceased members. Please email submissions to Susie Klein at sklein@cobar.org. High-resolution photos are appreciated.
Gerald A. Caplan
October 15, 1931–June 26, 2024
Gerald A. “Jerry” Caplan, noted attorney and cofounder of the Boulder-based law firm of Caplan & Earnest LLC, passed away on June 26, 2024. He was 92.
Jerry helped establish education law as a distinct practice area within the legal profession, a practice area that is now taught as a class in law schools across the country. He cofounded Caplan & Earnest in 1969 to focus on representing public school districts across Colorado, and today more than half the school districts in Colorado are clients. He also served as lead attorney in several cases that established the legal framework for the law surrounding public education, including Lujan v. Colorado State Board of Education, a landmark school finance case that resulted in significant legislative changes to financing of public education in Colorado and established the foundation for local community control.
Jerry earned his bachelor’s and JD degrees from Syracuse University, and then served in the Judge Advocate Generals Corps of the Army before starting his law practice in Boulder. He immediately established a reputation as a skillful trial and appellate attorney, earning his first victory in front of the Colorado Supreme Court in 1963. His name appears in more than 50 published judicial decisions.
Jerry served as chair of the Board of Trustees of the University of Northern Colorado and as adjunct faculty member of the University of Colorado’s School of Journalism, teaching First Amendment Law. He held the offices of president of the Boulder County Bar Association, Boulder County Public Trustee, Boulder municipal judge, and special assistant attorney general of Colorado. Caplan was the founding president of the Colorado Council of School Attorneys, president of the National School Boards Association Council of School Attorneys, the second recipient of the organization’s Lifetime Achievement Award, a Fellow of the American Bar Foundation, and a Fellow in the American College of Trial Lawyers, one of the most selective honors in the legal community.
Jerry is survived by his wife Betsy, daughter Lindsay (Ford) Smith, son Jeffrey (Emily) Caplan, and grandchildren Kendall Smith, William “Fordie” Smith, Lucy (Chase) Caplan, and Laurel Caplan.
Cuba Y. Hollaway
February 6, 1927–June 16, 2024
Cuba Y. Hollaway passed away on June 16, 2024, at 97 years of age. In the last 10 years of his life, he went scuba diving in Honduras, deep sea fishing in Costa Rica, and on cruises to Alaska and the Caribbean. He lived with his daughter but always remained independent and enjoyed mowing the grass on his riding lawn mower, watering the yard, going out to eat with family and friends, and spending time with his daughter and many pets. He was a loving husband, devoted father, loyal business partner, and friend, and he will be greatly missed by all who knew him.
Cuba was born on February 6, 1927, in Sulphur, Oklahoma, to Ruby Mae and Joy Roy
Hollaway. After graduating from Byrd High School in Shreveport, Louisiana, in 1945, he briefly attended Louisiana State University on an athletic football scholarship but left to join the United States Navy at age 17. He honorably served during WWII from March 9, 1945, until the end of the war and was awarded the World War II Victory Metal. He was an aviation ordnance-man third class aboard aircraft carrier USS Rudyerd Bay in the Pacific. After the war, he was a second lieutenant in the US Air Force Reserves.
Cuba attended college and law school on the GI Bill and an athletic football scholarship. He graduated with a BA in business administration from Southern Methodist University in Dallas, Texas, where he also attended two years of law school. He received his JD from the University of Wyoming in 1953. For 10 years he practiced law in Wyoming in both private practice and as a partner in the law firm of Halsey, Whitley, Hollaway & Liamos.
In 1964, he moved his family to Colorado Springs and raised them in the beautiful Rocky Mountains. He was a deputy district attorney in the El Paso County District Attorney’s Office for several years and prosecuted the first murder case in 20 years that resulted in a death sentence verdict. He practiced law in Colorado for over 50 years and was a partner in the law firm of Bennett & Hollaway. The El Paso County Legal Secretaries Association named him “Boss of the Year” in 1991–92, and he loved and respected his loyal secretaries, Dolly and Lois, of over 20 years.
Cuba had many interests and contributed much to his community. He was involved in the National Little Britches Rodeo Association for many years and served as president in 1976. He was a Shiner at the Al Kaly Temple in Colorado Springs since 1972. He and his wife enjoyed playing golf and spending time on their houseboat on Lake Pueblo. He was an animal lover and had many pets, including cats, dogs, horses, pigs, rabbits, chinchillas, chickens, ducks, peacocks, and an African Grey parrot. He was also a talented poet, cartoonist, and inventor, and he loved history and English literature.
Cuba was a devoted and loving family man, always honoring the memory of his parents, grandparents, two brothers, aunts, uncles, and cousins. He married the love of his life and high school sweetheart, Betty, on June 16, 1957, and they celebrated their 50th wedding anniversary before she passed away. He was also an adoring and supportive father, grandfather, and uncle. His son, Joe, preceded him in death. He is survived by his daughter Rebecca, grandchildren John and Lindsay, five great granddaughters, and nieces and nephews.
Memorial contributions in his name may be directed to St. Jude Children’s Research Hospital, stjude.org; Shriner’s Children’s Hospital, shinerschildren.org; or Pikes Peak Humane Society, 610 Abbot Lane, Colorado Springs, CO 80905.
Lloyd Leonard Rich
October 16, 1941–June 2, 2024
Lloyd Leonard Rich was born in Brooklyn, New York, to Alfred Irving Rich and Ruth Pearl Lampel. He grew up in Edgemere, New York, where he honed his athletic skills playing baseball and football. These skills earned him a full sports scholarship at Marietta College.
After graduation, Lloyd enlisted in the Air Force and was stationed with the 48th Tactical Fighter Wing at Lakenheath, England. While there, he enrolled at Sydney Sussex College at Cambridge University and began his studies in economics. While at Cambridge, he joined the basketball team and played against former New York Knicks star and future New York Senator Bill Bradley, who was a Rhodes Scholar at Oxford University at that time. He met and married Luisa Fabris and after his tour was over, he left the Air Force and moved to New Jersey, where his son Claude was born. Lloyd enrolled at the New School of Social Research in New York City and pursued a doctorate in economics.
Lloyd began his career in publishing by taking a sales job at Prentice Hall. He rose through the ranks, and in 1979, he became president of Prentice Hall Media at the age of 38. When that company was sold to Simon & Schuster, Lloyd spent a year as a vice president of that company and then left to become a consultant with Mosley & Associates, focusing on mergers and acquisitions.
While Lloyd lived in New Jersey, he took up tennis, and he and Claude traveled all over the country playing in father/son tournaments. Later in life, he took up golf. Lloyd was a huge Yankees fan who cherished his sculpture of the Yankees 1927 “Murderers’ Row,” which sat atop his desk throughout his lifetime.
When Lloyd turned 50, he decided to follow in his brother’s footsteps and go to law school. He enrolled at St. Mary’s University in San Antonio, Texas, in 1990. That year, he married his second wife, Carol Ann Waugh. After graduation, they moved to Denver and Lloyd started a new career as an attorney.
Lloyd was a leader in publishing law and assisted other attorneys in learning the arcane nuances of the field. One of his mentees, Steven Weigler, attests that Lloyd was an impactful legal mentor. “Lloyd had the combination of business sense, a wonderful personality, and a deep appreciation of the law. I would never be where I am without his patient advise and scholarship in trademark, copyright, and contract. He just had amazing qualities that I seek to emulate.” He worked until he retired at age 80. Despite Lloyd’s new focus, he and Carol always found time to support their extended family, their grandchildren, and many nieces and nephews. His untold influence on the lives he has touched will resonate for eternity.
Lloyd died peacefully on June 2, 2024, due to natural causes, and he will be immensely missed by his many friends, clients, and family members. He is survived by his wife Carol, his first wife Luisa, his son Claude, his grandchildren Valentina and Giorgio, and his brother Paul Rich.
John F. Rotole
July 9, 1943–April 30, 2024
John F. “Jack” Rotole passed away peacefully at home on April 30, 2024, with his true love, best friend, and spouse of 40 years, Jackie, at his side while being serenaded by Elvis.
Jack was a proud Denver native, born on July 9, 1943, to an Italian Irish family. He was one of nine siblings. He attended St. Philomena grade school, Cathedral High School, the University of Colorado, and the University of Denver law school. Jack loved being a lawyer and practiced law in Colorado for 52 years. He began his legal career as an assistant district attorney in the Denver District Court under Dale Tooley and Jarvis Seccombe. In 1974, he and two of his law school classmates started their own private practice, where he practiced criminal defense, plaintiff’s personal injury, liquor licensing, and commercial law until his death.
Jack was a highly successful, gifted, and skilled trial lawyer and negotiator who possessed considerable legal acumen for which he received many accolades. He was greatly admired by his peers, judges, and clients. Jack was a champion of the underdog, a fierce advocate, and a man of compassion. He had many high-profile clients and interesting cases throughout his career. His law partners, associates, and employees always appreciated his generosity, leadership, kindness, and wit.
Jack was charismatic, dynamic, and a true force of nature. He filled a room when he entered it. He was an eternal optimist, a loyal friend, and a loving spouse, grandfather, sibling, uncle, and cousin. His family members greatly admired him, loved being with him, and sought his advice. When you were with Jack, life just felt good. He had a sharp wit, keen intellect, and wonderful sense of humor.
Jack loved Denver, his many red Corvettes, his “rock and roll emporium,” horse racing, all the Denver professional sports teams, the CU Buffs, the Cherry Cricket, and traveling to Hawaii, Sanibel Island, and Italy. He was a huge Elvis fan. He liked to discuss and argue politics, philosophy, the law, current events, and sports. He was never at a loss for words.
Jack is survived by his spouse Jackie, his stepsons John (Christine) and Christian (Michelle) McConnell, and his grandchildren Isabella and Johnny McConnell. He was preceded in death by his parents and his brothers Phil, Joe, and Jimmy Rotole. He is also survived by his siblings Trudy (Jerry) O’Connor, Tom (Brooke) Rotole, Bob Rotole, Dick (Sheri) Rotole, Mary Yeager, Beverly Rotole (spouse of the late Phil Rotole), and numerous nephews, nieces, and cousins.
Memorial contributions in his name may be directed to the International Myeloma Foundation and the Denver Dumb Friends League.
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