Dennis Raymond Santoli

Dennis Raymond Santoli died peacefully in the company of family on January 25, 2026, in Naples, Florida. He was 79 years old. Dennis was preceded in death by his parents, Raymond and Dorothy Santoli, whom he revered. He is survived by his beloved wife of 27 years, Cynthia Booth. Dennis’s legacy shines brightest through his and Cynthia’s blended family, to whom he devoted all his love: two precious children and their spouses—Adriana Santoli (husband Jimmy Brown) and Nicolas Santoli (wife Heather); four esteemed brothers and their wives—Michael (wife Jan), Donald (wife Caryn), Mark (wife Marielena), and David (wife Gladys); two adored step-children and their spouses—J.P. Cooney (wife Maureen) and Meghan Rinehart (husband Michael); 13 cherished grandchildren and step-grandchildren—Steven, Nicole, Alaina, Brayden, Gabriella, Aaron, Maximus, Joshua, Eleanor, Ryan, Connor, Mary, and Annie; six treasured great grandchildren—Wyatt, Easton, Barrett, Walker, Carter, and Caylee; six dear nephews and nieces—Denise, Traci, Anthony, Joseph, Daniel, and Marcus; 42 admired first cousins; and scores of Sigma Chi Fraternity brothers, friends, business partners, employees, and in-laws—all of whom Dennis considered and treated like family. Dennis was immensely proud of the family with which he was blessed through blood and that he built through marriage and lived experience. Dennis Raymond Santoli, the eldest of five sons to Raymond and Dorothy Santoli, was born on February 12, 1946, in Cleveland, Ohio. Dennis’s father Ray, the son of Italian immigrants, started and managed a thriving insurance business in Cleveland; Dorothy, the granddaughter of Polish immigrants, was a devoted homemaker. The Santolis made their original home in a modest house on Dove Avenue in Cleveland proper. As the family and Ray’s insurance business expanded, when Dennis was still a young boy, they left Dove Avenue for a three-bedroom home with one bath in Walton Hills, a suburban village in Cuyahoga County about 30 minutes southeast of the city. Ray and Dorothy raised five sons in that home and remained there until they passed away in 2007 and 2018, respectively. Ray and Dorothy afforded Dennis and his brothers a warm and supportive upbringing—rich in faith, community, and family ritual. The Santolis were parishioners at St. Mary of the Immaculate Conception in Bedford, where Dennis solidified his enduring Catholic faith; they were active in Cleveland’s Italian American Golf Association and countless civic endeavors; and they hosted large and boisterous Fourth of July, Labor Day, Thanksgiving, Christmas, and Sunday gatherings of their extended Italian and Polish families, which often featured Dorothy’s homemade ravioli and spaghetti sauce. Dennis so admired his parents, whose love and exemplar were the foundation for the family, business, and legacy Dennis would build for himself. Dennis attended Bedford High School, where he distinguished himself as a student—he graduated near the top of his class—and as an athlete—he was a four-year letterman on the wrestling team. He went on to become one of Bedford High’s most distinguished Bearcats, earning induction to its alumni Hall of Fame later in life. He graduated from Bedford in 1963 at the age of 17 and went on to college at Western Reserve University—now Case Western Reserve University—in Cleveland. Dennis intended to commute from home during college, but the birth of his youngest brother David that year necessitated that he move out—the Santoli family’s Walton Hills home was just too snug for a college freshman and infant son to bookend the three other Santoli brothers, Michael, Donald, and Mark. Dennis moved in with his immigrant grandparents, Matteo and Teresa, who, in addition to putting a roof over Dennis’s head, taught him to cook the delicious traditional Italian meals that he later became renowned for preparing. In 2017, Case Western Reserve recognized Dennis as a Distinguished Alumni of the Year in recognition of his life achievements, his role as an Alumni Admission Ambassador, and his service as a member of the Dean of the College of Arts and Sciences’ visiting committee. But neither the classroom nor his grandparents’ kitchen had the greatest impact on Dennis during his college years. That came through his initiation into Sigma Chi, a fraternal brotherhood devoted to Friendship, Justice, and Learning. Dennis embraced those values at Western Reserve, where he was a charter member of the Beta Alpha Chapter, and held them close throughout his life. He strove always to meet the Fraternity’s Jordan Standard, which simply reads: The standard with which the Fraternity started was declared by Isaac M. Jordan to be that of admitting no man to membership in Sigma Chi who is not believed to be: A Man of Good Character, A Student of Fair Ability, With Ambitious Purposes, A Congenial Disposition, Possessed of Good Morals, Having a High Sense of Honor, and A Deep Sense of Personal Responsibility. Inspired by that Standard, shaped by Santoli values, and armed with a Western Reserve degree and unrelenting work ethic, Dennis headed east to the National Capital Region in 1967. Although he remained ever connected to his Cleveland roots, Dennis never looked back. In 1967, Dennis enrolled in Georgetown University Law Center, a premier Catholic law school run by Jesuits, whose mission to train “Men for Others” resonated with his upbringing and morals. Most law students attend full time—not Dennis. He doubled as a law student and bank employee to pay his tuition and support a new family—his first daughter, Adriana, was born in 1970. Dennis’s legal education was interrupted by the Vietnam War. He was drafted into active duty and commissioned as an Army First Lieutenant on July 23, 1970. Dennis was spared armed conflict—he was assigned to a military base in Germany where he conducted fraud investigations. He earned an honorable discharge on March 24, 1972, enabling him to complete his law degree under the GI Bill. So moved by his military service, Dennis reenlisted in the Army Reserves, from which he retired in 1985 as a Major. Following law school, Dennis joined a Washington law firm specializing in civil litigation. But his law practice lasted only briefly—the entrepreneurial spirit and fierce independence instilled by his father rapidly drew Dennis into business. For approximately 15 years, Dennis managed a major national firm specializing in underwriting insurance for psychiatric hospitals. In 1992, Dennis struck out on his own. Using personal savings and investments entrusted to him by faithful friends and family members, Dennis launched The Campania Group, named for the region in southern Italy from which his grandparents immigrated to the United States. The Campania Group offered professional liability solutions for a range of small- and middle-market healthcare providers, including durable medical equipment suppliers, behavioral health specialists, eldercare providers, and podiatrists. Dennis’s innovation, which distinguished Campania from competitors, was providing individually tailored risk management. Campania did not sell product lines—it sold Dennis and his team’s expert foresight and counsel. Dennis prided himself in personally answering the phone when clients called. He carefully anticipated and mitigated clients’ risks; stood by their side through high stakes litigation and unforeseeable hazards; and scrupulously safeguarded their viability, including traveling to London each year to look Lloyds’ underwriters in the eye to make sure no client would ever be abandoned or suffer a shortfall. Dennis had the unique vision and disposition to combine good business with good practice, bringing superior attention and sincere personal service to bear on risk and crisis management so that healthcare professionals could focus on serving patients and customers. By 2010, Dennis had grown Campania to 40 employees with service accounts in 30 states and the District of Columbia. That year, he negotiated Campania’s acquisition by The Hanover Insurance Group, a publicly traded titan in the insurance industry. Dennis conditioned the Hanover deal on the company’s loyalty to Campania’s employees—to which Hanover agreed; and Hanover conditioned the deal not just on obtaining Campania’s portfolio, but also on ensuring Dennis’s continued leadership—to which Dennis agreed. Dennis promised to join Hanover as president of its healthcare division for three years; he remained for six, helping to establish Hanover as an industry leader in end-to-end insurance solutions for healthcare businesses. And just as he did with his original Campania employees—many of whom remain with Hanover to this day—Dennis kept his word to the clients who put their trust in him. Even after retiring, Dennis staked his own estate on continuing to insure and personally manage the risk of the existing litigation claims against Campania’s original clients. When all was said and done, Dennis’s principled and steadfast leadership of Campania rewarded the faith of the family and friends who bet on him in 1992, protected the well-beings of the employees he hired, and sustained the viability of the small healthcare businesses that entrusted him to insure their livelihoods. Following in and extending beyond the footsteps of his father, Dennis personified integrity, ethics, and personal responsibility in business. Dennis’s success in business was eclipsed only by his achievement as a father and Santoli patriarch. In addition to his daughter Adriana, Dennis was blessed with his son Nicolas in 1977. A single father, Dennis raised Adriana and Nic in Vienna, Virginia. Both graduated from James Madison High School and became the first Santoli grandchildren to attend and graduate from college—Adriana from Marymount University and Nic from George Mason University. Both joined Dennis at The Campania Group—Adriana as an underwriter, a profession in which she continues to this day; and Nic to develop and manage the company’s information technology, a profession in which he also continues. Dennis raised Adriana and Nic in the Vienna home on Wexford Way that he purchased in 1982, and that he lived in the remainder of his life. Dennis cherished his Wexford Way home, making it equally as warm and welcoming as the home in which he was raised in Walton Hills. Dennis frequently hosted Sunday Italian-style gatherings of friends, family, Campania employees, business partners, and Sigma Chi brothers, for whom he prepared generous meals and shared copious amounts of Italian wine and limoncello; outdoor pig roasts; Italian card games (briscola and scopa were his favorites); family reunions; large Easter, Christmas, and Thanksgiving gatherings; a much loved barbeque of kielbasa and Italian sausage the Sunday afternoon before the annual Campania Charity Golf Outing; and countless special events, including baby showers, engagement parties, charity fundraisers, and even weddings. Dennis’s Wexford Way home was the source of much joy and a throughline of Dennis’s dedication to family, friends, community, and business. The joy at Wexford Way spread and became more profound in 1998, when Dennis married Cynthia Booth, to whom he pledged and gave all his love. Over 27 years, they shared a blended family of children, grandchildren, great grandchildren, siblings, nephews and nieces, cousins, and in-laws. Dennis loved and cared for Cynthia’s children, J.P. Cooney and Meghan Rinehart—and their families and extended families—as his own; and Cynthia embraced Dennis’s family with equal love and vigor. Together, Dennis and Cynthia fortified Wexford Way as the home and epicenter of their combined family. They were business partners as well, sharing together in the success and fruits of Campania, including the gift of retiring together. In 2013, Dennis and Cynthia opened a winter home in Bonita Springs, Florida. Together, they strove to make Bonita Springs a southern outpost of Wexford Way—a home of abundant warmth, generous hospitality, and long-lasting memories. Dennis relished hosting grandchildren over school breaks and watching them splash in the back porch pool, welcoming friends and family from the north seeking respite from the cold weather, and spending more dedicated and quiet time with Cynthia in the warm climate. He took delight in weekly golf rounds, competing in bocci at the Pelican Isle Yacht Club—Dennis proudly captained a three-time club championship team—and indulging more dinners out after devoting so much time to cooking for others. More broadly, in retirement Dennis cherished traveling in Italy and throughout Europe with Cynthia, teaching grandkids to prepare the same Italian meals he learned from his mother and grandparents, playing golf with the Retired Men’s Golf Association and hosting the annual Italian American Open at his treasured Westwood Country Club, and cheering on his long suffering Cleveland sports teams. He devoted substantial time to philanthropic pursuits, serving as a corporate member of the Board of Directors of The Robert A. Facchina Italian American Museum of Washington, D.C., supporting educational causes through his own Blue and Gold Foundation, and, most of all, remaining active in Sigma Chi. Though nothing gave Dennis more pride than The Campania Group, or more pure joy than his family and friends, he found deep purpose and personal reward as a loyal and faithful servant of Sigma Chi’s White Cross. Dennis exemplified the Jordan Standards of character, ambitious purpose, good morals, honor, and personal responsibility, and he personified and relentlessly promoted Sigma Chi’s core values of Friendship, Justice, and Learning. Dennis was initiated into the Beta Alpha Chapter of Sigma Chi at Western Reserve University on February 1, 1964. He served his undergraduate chapter as Recruitment Chairman, Quaestor (treasurer), and Pro Consul (vice-president). Dennis became a Life Loyal Sig in 1995 and served as an alumni chapter president, Grand Praetor (regional governor), and as a member of nearly every major Fraternity committee, including as a longtime member of the Executive Committee. In 2004, Dennis was inducted into the Order of Constantine, Sigma Chi’s highest honor for dedication and service to the Fraternity; and in 2015 he was named a Significant Sig, an honor recognizing brothers whose exemplary achievements in their fields of endeavor have brought honor and prestige to the name of Sigma Chi. Dennis also received numerous Certificates of Achievement and Grand Consul Citations. In 2011, Dennis was elected Sigma Chi’s 67th Grand Consul, the Fraternity’s highest office—a position he was privileged to occupy and which he counted as perhaps his proudest personal achievement. During his two-year term, Dennis visited dozens of undergraduate chapters, enhanced individual chapters’ attention to risk management, and hosted more than 600 delegates in Washington, D.C. for the Fraternity’s 79th Grand Chapter convention. Upon his tenure’s end, Dennis joined the Board of Directors of Sigma Chi’s Risk Management Foundation, which he chaired for more than a decade until his passing. Dennis truly adored and respected his Sigma Chi brothers. He appreciated hosting them at Wexford Way and in Bonita Springs, periodically vacationing with them in the Outer Banks of North Carolina, competing at countless Sigma Chi charity golf outings, and mentoring young brothers in business and in life. Dennis was enormously proud that his brothers Michael and David and son Nic were also his brothers in Sigma Chi. A Catholic funeral Mass will be held for Dennis at Holy Rosary Church—Chiesa del Santo Rosario—in Northwest Washington, D.C., on Saturday, February 14 at 11:00 a.m. Thereafter, Dennis’s Sigma Chi Fraternity brothers will conduct a White Rose Ceremony, a public recognition of his entrance into the Chapter Eternal and a final tribute to his life and 62 years of loyal and faithful service to the White Cross. The White Rose Ceremony will be conducted at Casa Italiana Sociocultural Center, which is connected to Holy Rosary and home of The Robert A. Facchina Italian American Museum of Washington, D.C.—which Dennis supported generously and on whose Board of Directors he served. A repast will follow at 1:30 p.m. at Westwood Country Club in Vienna, Virginia—where, across five decades, Dennis savored friendship and companionship. All are welcome. Parking for the funeral Mass and White Rose Ceremony will be available on the street and in the Capitol Crossing parking garage located at 3rd and G Streets, Northwest, for which vouchers will be provided at the church. In lieu of flowers, Dennis’s family kindly requests that those who wish to honor his legacy— for character, ambitious purpose, good morals, honor, and personal responsibility—perform in his name any act of goodwill or charity to an individual or organization of their choosing.

Dennis Raymond Santoli

February 12, 1946 - January 25, 2026