Raymond Chavez and Rupert Keesler: A Legacy of Love and Humility

Raymond Chavez and Rupert Keesler: A Legacy of Love and Humility
From left to right: Raymond Chavez and Rupert Keesler

Raymond (Ray) Chavez and Rupert Keesler, both former San Diegans and transformational philanthropists, were best friends, business and life partners for more than 65 years.

Ray, born in 1925 and Rupert, born in 1923, met as they were beginning new careers shortly after serving in the military. To say they formed an immediate bond would be an understatement.

Ray’s degree in economics helped with their business development and led to his love of debating economic policies, while Rupert’s degree in social work was the perfect complement to drive the couple’s success. Together, they amassed significant wealth by purchasing and developing land and commercial real estate across California and Arizona.

But it was never about accumulating money. It was how they could use it.

They cared very much for each other and were happy to live and work together in Escondido. Over the course of their lives, Ray and Rupert were always finding ways to give back to the community, and they had a deep love for animals and people.

As Ray put it, he “made it in America” and was proud of his Chicano heritage, which meant that he also had a responsibility to help others with similar backgrounds. As a result, Ray and Rupert developed programs for underserved Chicanos at the high school and college level, one of many initiatives and charitable causes they supported.

Selfless Philanthropists

Together, Ray and Rupert lived a life for others.

Although they could afford to live a life of luxury, that was never their desire. They preferred to keep a low profile and live humbly, while sharing all that they could with those who needed it most.

Rupert’s estate planning attorney Laura Nichols shared a memory that perfectly encapsulated the couple’s personality. While at a grocery store shopping together, Laura asked Rupert what he wanted to get and he responded, “Apples and ice cream.” When she asked what type of ice cream, he quickly answered, “The kind that is on sale.”

Today, Ray and Rupert’s legacy lives on through the charitable causes they supported and the endowed legacy funds at The San Diego Foundation that continue to make a difference.

Ray and Rupert always said that they wanted as much of their money to go to charity as possible.

After Ray passed away in 2013, Rupert actively engaged more nonprofits and worked with The San Diego Foundation to donate more of his assets to charity, including gifting the condominium he lived in when he moved into a retirement home.

Rupert would pass away a few years after, but shortly before that time, he told Laura to review a packet of financial documents on his kitchen table. The documents were his final will and trust. After looking at the documents, Laura asked him, “What are your thoughts about all this money going to charity?”

He said simply, “I lived a very good life and I hope that others can as well. This money will last for a long time and do a lot of good.”

In addition to donating real estate, Ray and Rupert both created Charitable Remainder Trusts with The San Diego Foundation which provided them with an income stream for life and consistent tax deductions. Most importantly, upon their passing, the value of those trusts, combined with their legacy gifts, was more than $35 million which has since gone on to help dozens of San Diego charitable organizations, helping orphans and foster youth, supporting the Episcopal Church, improving animal welfare, and numerous other passions of theirs.

Ray and Rupert were never the most well-known philanthropists in San Diego, but their impact is as deep as any.

Their humility is what made them special and their generosity will forever change the lives of San Diegans past, present and future.

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