Dennis Lynn Randall Jr.

Dennis Lynn Randall Jr. obituary, Aptos, CA

Dennis Lynn Randall Jr.

Dennis Randall Obituary

Obituary published on Legacy.com by Santa Cruz Watsonville Cremation & Burial Service on Feb. 19, 2026.
Dennis L Randall Jr. passed peacefully at home in Aptos, CA on Wednesday January 14th, after being diagnosed with cancer in December of 2023, which he battled courageously and trusted God's plan for his life.

Dennis was born on April 1, 1964, to his parents Dennis Lynn Randall and Carolyn Anne Luck Randall at John Gaston Hospital, in Memphis TN, where his father was a resident. His first 8 years were in Nashville while his father served with the Marine Corps and Naval Reserves Medical Corps. The family then moved to Tustin, CA where Dennis Sr. completed his residency at UC Irvine. Dennis and his younger siblings, Gregory and Kristen, spent their childhood growing up in Tustin. Dennis attended Foothill High School and played on their CIF championship football team. Dennis attended Orange Coast College for 2 years before he transferred to the University of Southern California, graduating with a BA in Political Science. He was affiliated with the Alpha Upsilon chapter of the Sigma Chi Fraternity.

In 1987, he began his 40-year career in commercial real estate specializing in property management, marketing and development. He worked for the Paragon Group, Cushman & Wakefield, Prometheus Development and Opus Group. He founded Insight Development Partners in June of 2004 to take advantage of real estate opportunities in the Bay Area and Silicon Valley. He was also part of Insight Realty Co., Acquity Realty and Acquity Capital Group in recent years. He served for many years on the San Jose Downtown Association and was a founding member of the Downtown Committee for the Silicon Valley Chamber of Commerce. Dennis was also a member of numerous feedback and selection committees for both the City of San Jose and the San Jose Redevelopment Agency. He was known to be a fierce negotiator with a brilliant, creative mind for land use and development opportunities. He loved his chosen field driven by his love and protection of his family. He was a generous man of integrity and loyalty in all things.

Dennis married "smokin' hot" Brooke Manchee Randall in August of 1993 in Pasadena, CA. They loved and supported each other through thick and thin. They led an adventurous life, moving often over their 32-year marriage, raising their children, Pearson and Portia, in Los Gatos, CA. Dennis was baptized into the Catholic faith in 2004 at St. Mary of the Immaculate Conception in Los Gatos. Their St. Mary's community has been central to their lives ever since. He was always most proud of being a father and husband.

Dennis was beloved for his irreverent humor, intelligence, passion for his faith and political dialogue. Dennis loved skiing, golfing, fly fishing, Trojan football (Fight On!!) and travel. His final overseas trip was to Lourdes, France, seeking healing from our Lady of Lourdes. Wine tasting was a favorite pastime, with weekend trips to Sonoma and Napa in the 1990's; his favorite appellation was the Santa Cruz Mountains after moving to Aptos in 2020. He loved life on the Northern California coast, where he enjoyed beach walks with Figgy, the beloved family corgi…the only dog he ever had.

Dennis is survived by his wife Brooke; son Pearson of San Jose, CA; daughter Portia of Brooklyn, NY; brother Gregory of Murrieta, CA; and sister Kristen Berens (Shawn) of Indianapolis, IN. Dennis was godfather and "Uncle Awesome" to his nephews Jackson and William Berens.

A memorial mass celebrating Dennis' life will be at St. Mary of the Immaculate Conception, 219 Bean Ave, Los Gatos on March 6, 2026 at 3pm. A private reception will be held following. In lieu of flowers, please consider a donation to the Order of Malta, Western Association, USA for the benefit of the Lourdes Pilgrimage (add to notes). https://orderofmaltawestern.us/donate/

To plant trees in memory, please visit the Sympathy Store.

Sign Dennis Randall's Guest Book

Not sure what to say?

March 9, 2026

Phillip La Plante posted to the memorial.

February 25, 2026

Cara Peracchi Douglas Heneweer posted to the memorial.

February 19, 2026

Santa Cruz Watsonville Cremation & Burial Service posted an obituary.

2 Entries

Phillip La Plante

March 9, 2026

All honor to your name Dennis. You were the definition of a Trojan. See you in the Chapter Eternal. In hoc signo vinces. Fight On!

Cara Peracchi Douglas Heneweer

February 25, 2026

Dennis Randall... Wow. I could fill a book with the wonderful memories of our time together.

To begin at the beginning, I want to thank Dennis - because he took me in when I was truly broken, healing from the recent loss of my late husband. In that fragile season, Dennis became an instant friend and protector. He was a big brother in spirit, a kind and steady soul whom I first met through my dearest friend, "Brookie". Yet beyond that connection, Dennis and I built a friendship entirely our own.

Together, we worked to help rebuild the City of San Jose after the recession. I remember telling him, half-laughing, "I took the job because I was a mess - and so was the City." Dennis understood that perfectly. He had a way of finding humor at the most unexpected moments, a gift that could lift even the heaviest day. He made me laugh when I needed it most. And yes - his unwavering opinions could frustrate me - but through it all, he ALWAYS had my back.

Dennis was a beautiful blend of contradictions: kind and silly, focused yet serious, strong yet deeply gentle. I loved him dearly. He was my friend, and he knew I was his friend too.

I will miss so many things. Our Dennis-Curated Santa Cruz Mountains Wine Tours, where nothing short of spectacular! New Year´s celebrations in Truckee that will never feel quite the same. Amazing meals made and enjoyed, trips, walks, quiet moments, laughter, and most of all, our conversations about life and the great beyond.

And in close, I'd like to send a message to my dear friend, Dennis Randall... So Dennis, now that you have taken the lead, forge ahead. Make a place for us where we may someday meet again in His glory. You have built a path, and one day we will find our way to you there.

Until then, you will be deeply missed, lovingly remembered, and forever cherished, your rascal spirit and all!

With love always,
Cara

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Santa Cruz Watsonville Cremation & Burial Service

550 Soquel San Jose Road, Soquel, CA 95073

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Sign Dennis Randall's Guest Book

Not sure what to say?

March 9, 2026

Phillip La Plante posted to the memorial.

February 25, 2026

Cara Peracchi Douglas Heneweer posted to the memorial.

February 19, 2026

Santa Cruz Watsonville Cremation & Burial Service posted an obituary.