Thomas Jack Riddle was born in Oklahoma City, August 14, 1936, the third child of JD and Ruby Riddle. He was born with a veil on his face, which portends good fortune. Indeed, Tom lived a life that was full of good fortune.
The titles for Tom Riddle are many — husband, father, grandfather, great-grandfather, brother, brother-in-law, uncle, friend, technology innovator, realtor and property manager, blue water sailor. Tom developed a great love of the sea and sailed with many a wind off his starboard quarter.
Tom died quietly, October 23, at home. He and his wife Debbie (O’Toole) were holding hands and listening to Hawaiian music when he took his last breath. He was a happy and fulfilled man.
Tom’s early childhood was influenced by life as a migrant family that followed labor opportunities, working in mines in Cottonwood, AZ, Twenty-Nine Palms and Sheep Ranch, CA in the Sierra foothills.
“Little” Tom’s life was that of a “free range” child, tagging along behind brother and sister. Tom and his siblings lived by the simple rules:
“Don’t drink water from the creek” (arsenic was a byproduct of the mining process) and, “be home before dark.”
At the onset of WWII, the mines closed and the family migrated to Los Angeles in search of jobs in the defense industry. Tom’s formative years progressed, ultimately, in El Segundo, CA, where he attended high school. During this time, half way through his senior year, Tom joined the Marine Corps. It was here, in 1954, that Tom discovered his fascination and love for the sea, as one of 5,000 marines on board a troop ship steaming to Japan.
He graduated high school, married (Hallie Hutton), and started a family. Tom raised his family in Huntington Beach. Their marriage of 22 years ended in 1977.
Tom’s good fortune was further highlighted by a 30-year career in the computer industry, beginning in 1959 while working for Space Technology Lab as an apprentice programmer. This concluded with Tom becoming Director of International Sales for FileNet Corporation.
In the infancy of document image processing, Tom sold a system that, in 1988, had a starting price of $1 million dollars. That same technology is now the “scan” feature on your smart phones.
Tom’s career was punctuated by his participation in developing cutting edge technology, much of that being in banking and communications. His enthusiasm and willingness to volunteer for any and all new product development challenges took Tom to more than 12 countries, creating business relationships with countless companies and industries.
In 1969, Tom’s oldest son, Steven, had just finished reading “Moby Dick.” He came to his dad and said “Dad, we need to buy a sailboat,” to which Tom replied, “Well, Steve, we have two problems. One: we don’t know how to sail. And two: we don’t have any money!”
Steve replied, “I’ll take care of the first part, you take care of the second part!”
Not long after this, Tom saw an ad in “Sports Illustrated” for a 12-foot boat that could be purchased for $88 (and “two end flaps from a carton of Kool Cigarettes.” The purchase of that little Kool boat started Tom, and his entire family down through the generations, on a trajectory that figures prominently in the lives of each and every one of his family. In 1981, Tom’s good fortune continued. He purchased a larger boat, and was introduced to his wife of 41 years, Debbie, while working at a start-up computer company in Irvine, CA.
He was living on his 38’ sailboat in Newport Harbor at the time. In one of their first conversations Tom told Debbie “when I turn 50 I’m going to sail away.” They married in 1984 and set in place a “five-year plan” to accomplish that dream.
In 1988 they sailed away on, what would become, a three-year, 15,000-mile blue-water journey upon their Downeast-38 sailing yacht, Pelican. Despite the hardships of blue water sailing, both Tom and Debbie carried specific memories they never tired of sharing.
“I’ll never forget sailing into the harbor in the Marquesas under a full moon,” said Tom. “We could smell the island long before we could see it — the organic smell of vegetation that is so suddenly divergent to the smell of the sea.”
All it took was one South Seas port-o-call to convince the Riddles that sailing around the world wasn’t so important after all. They ended up spending three months in the Marquesas, tossing their carefully planned agendas and deadlines overboard while enjoying the climate and sailing that the South Pacific has to offer.
It was en route to Huahine that “adventures in paradise” for Tom and Debbie Riddle hit a near-devastating turn of events. They were mid-ocean and under a full spread of sail. It was dark, and a 72-foot party boat crashed into their sloop.
Tom and Debbie had been sailing on alternate six-hour shifts. The accident took place just after midnight on Debbie’s watch. She heard a “bang” and Tom was thrown from the bunk down below. “Tom came up to see what had happened,” said Debbie. “He thought we hit a submarine. I thought we hit the island.”
The two boats had collided, locked rigging, and by the time the other boat pulled free it had taken out both of the Downeast-38’s lower port shrouds, nearly toppling their mast. Fortunately, no one was injured.
The offending vessel continued on into the night with their lights off. A cruising couple the Riddles had met in Mexico was fortunately sailing in-company with the Pelican at the time. They motored with them 60 miles to Raiatea, the only other place outside of Hawaii and Tahiti with a hoist large enough to lift their boat out of the water.
Upon their return from this massive adventure, Tom’s good fortune continued as he and Debbie embarked upon another 30-year career, this time in real estate sales and property management. First working for his father-in-law, Lee Mather, and ultimately buying Lee Mather Company, a Coronado institution and Coronado’s oldest real estate brokerage, from Phyllis and Lee Mather in 1998, along with business partner Mike Herlihy.
Tom enjoyed a rich, full life, with countless friends, a loving and devoted family, and endless adventures. He led a vigorous life until a heart attack in May of 2025 diminished his condition. Tom ultimately succumbed to congestive heart failure.
Special thanks and gratitude to Norma Peńa, and her band of angels, as well as the entire team at Radiant Hospice, who were there for Tom and Debbie these past months. Debbie reflected on those who helped make Tom’s passing comfortable. “Their care and attention to all our needs was so special, filling each of Tom’s final days with love and affection. He especially enjoyed having a new audience for his numerous stories, many of which were recorded for posterity.”
Tom is survived by his wife Debbie, his daughter, Cindy (Greg) Newman of Corona Del Mar, son Jim (Kris) Riddle of San Clemente, grandchildren, Jessica (Max) Moosmann (Costa Mesa), Dylan Newman (Costa Mesa), Holley (Kye) See (Tulsa OK), Cameron Carlson Riddle (San Diego), Merrik Riddle and Maliea Riddle (San Clemente). He is also survived by great grandchildren, Josephine and Tommy Moosmann, brother, Bob Riddle (San Diego), sister Susan Harris (Las Vegas) and numerous nieces and nephews. Tom was pre-deceased by his son, Steven.
A Memorial Service is set for Sunday, December 7, 2025, 12:30 p.m., at the Coronado Golf Course. A short reception will follow.
Tom donated his body to the Willed Body Program at Western University of Health Sciences (alma mater of granddaughter, Holley, and grandson-in-law Kye See).
In the words of his granddaughter, Dr. Holley See: “He is in great hands at Western University. The things I learned from donor-patient relationships continue to influence my understanding and practice of medicine daily.”
In lieu of flowers, the family requests that donations be made, “In Memory of Tom Riddle,” to Western University of Health Sciences (COMP-Northwest):
200 Mullins Dr.
Lebanon, OR 97355-3983
(541) 259-0200
For information on Willed Body Donation:
https://mediaweb.westernu.edu/Mediasite/Play/ff7771e7b8b34b459df9a5fe3b5779621d
Editor’s Note: A terrific adventure of Tom and Debbie’s sailing voyage can be found at the link below:
TOM AND DEBBIE RIDDLE: From South Seas Adventurers To Coronado Realtors (Long Version)
Tom was a man who always had a smile on his face. He was such a gracious neighbor to all of us. He lived a full life and was due every blessing he received.
Til we meet again,
The Lowerys
What a great person…Tom was just a true gentleman and he’ll be missed.
This was really well written. Good to see that small town journalism is still alive.